Peptides are heteropolymers composed by amino acid residues linked by peptidic bonds between the carboxyl group of one amino acid residue and the α-amino group of the next one. The definition is rather vague in terms of chain length, peptides ranging from two residues to a few dozens residues. Its upper limit of molecular mass has been set rather arbitrarily in 6,000 Da. The size of the molecule determines the technology most suitable for its production. Recombinant DNA technology is particularly suitable for the synthesis of large peptides and proteins, as illustrated by the case of insulin and other hormones (Walsh 2005). Chemical synthesis is a viable technology for the production of small and medium size peptides ranging from about 5 to 80 residues (Kimmerlin and Seebach 2005). Enzymatic synthesis is more restricted and has been hardly applied for the synthesis of peptides exceeding 10 residues. Its potential relies on the synthesis of very small peptides and, in fact, most of the cases reported correspond to dipeptides and tripeptides (Kumar and Bhalla 2005). In this sense, the technologies for peptide production are not competitive with each other in most of the cases.
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References
Abrahamsen L, Tom J, Burnier J et al. (1991) Engineering subtilisin and its substrates for efficient ligation of peptide bond in aqueous solution. Biochemistry 30:4151-4159
Adamczak M, Hari Krishna S (2004) Strategies for improving enzymes for efficient biocatalysis. Food Technol Biotech 42(4):251-264
Ahn, JM, Boyle NA, Macdonald MT et al. (2002) Peptidomimetics and peptide backbone modifi-cations. Mini Rev Med Chem 2(5):463-473
Albericio F (2000) Orthogonal protecting groups for Nα -amino and C-terminal carboxyl functions in solid-phase synthesis. Biopolymers (Peptide Sci) 55:123-139
Ambulos NP, Bibbs L, Bonewald LF et al. (2000) Analysis of synthetic peptides In: Kates SA, Albericio F (eds). Solid-phase synthesis: a practical guide. Marcel Dekker, New York, pp 751-789
Amorim Fernandes J, McAlphine M, Halling P (2005) Operational stability of subtilisin CLECs in organic solvents in repeated batch and continuous operation. Biochem Eng J 24:11-15
Andersson L, Blomberg L, Flegel M et al. (2000) Large-scale synthesis of peptides. Biopolymers 55:227-250
Arnold F (2001) Combinatorial and computational challenges for biocatalyst design. Nature 409:253-257
Aso K (1989) Enzymatic approach to the synthesis of a lysine-containing sweet peptide, N -acetyl-L-phenylalanyl-L-lysine. Agr Biol Chem 53:729-733
Baca M, Muir TW, Schn ölzer M et al. (1995) Chemical ligation of cysteine-containing pep-tides: synthesis of a 22 kDa tethered dimer of HIV-1 protease. J Am Chem Soc 117:1881-1887
Baile C, McLaughlin C, Della-Fera M (1986) Role of cholecystokinin and opioid peptide in control food intake. Physiol Rev 66:172-234
Banfi D, Mutter M, Patiny L (2004) Versatile synthesis of Boc protected hydrazinoacetic acid and its application to the chemoselective ligation of TASP molecules. Protein Peptide Lett 11 (6):539-542
Barberis S, Illanes A (1996) Cat álisis enzim ática en fase org ánica. Ing Quim March :165-173
Barberis S, Quiroga E, Arrib ére MC et al. (2002) Peptide synthesis in aqueous-organic biphasic systems catalyzed by a protease isolated from Morrenia brachystephana (Asclepiadaceae). J Mol Catal B: Enzym 17:39-47
Barberis S, Quiroga E, Morcelle S et al. (2006) Study of phytoproteases stability in aqueous-organic biphasic systems using linear free energy relationships. J Mol Catal B: Enzym 38:95-103
Barlos K, Gatos D (1999) Fluorenylmethyloxycarbonyl/tbutyl-based convergent protein synthe-sis. Biopolymers 51(4):266-278
Barlos K, Chatzi O, Gatos D et al. (1991) Studies on anchoring of Fmoc-amino acids and peptide cleavage. Internat J Peptide Protein Res 37(6):513-520
Bj örup P, Adlercreutz P, Clap és P (1999) Useful methods in enzymatic synthesis of peptides: a comparative study focusing on kinetically controlled synthesis of Ac-Phe-Leu-NH2 catalyzed by α-chymotrypsin. Biocatal Biotransform 17(5):319-345
Bordusa F (2002) Proteases in organic synthesis. Chem Rev 102:4817-4867
Bordusa F, Ullmann D, Elsner C et al. (1997) Substrate mimetics mediated peptide synthesis: an irreversible ligation strategy that is independent of substrate specificity. Angew Chem Int Edit 36:2473-2475
Brahms S, Brahms J (1980) Determination of protein secondary structure in solution by vacuum ultraviolet circular dichroism. J Mol Biol 138:149-178
Bray BL (2003) Large-scale manufacture of peptide therapeutics by chemical synthesis. Nature Rev 2:587-593
Bruckdorfer T, Marder O, Albericio F (2004) From production of peptides in milligram amounts for research to multi-tons quantities for drugs of the future. Curr Pharm Biotechnol 5:29-43
Cabezas M, Del Campo C, Llama E et al. (1990) Organic reactions catalyzed by insolubilized enzymes. Part II. Influence of structure of the acyl donor in selectivity of α-chymotrypsin. J Mol Catal 62(3):353-367
Calvo JC, Choconta KC, Diaz D et al. (2003) An alpha helix conformationally restricted peptide is recognized by cervical carcinoma patients’ sera. J Med Chem 46(25):5389-5394
Cao L, van Rantwijk F, Sheldon R (2000) Cross-linked enzyme aggregates: a simple and effective method for the immobilization of penicillin acylase. Org Lett 2:1361-1364
Cao L, van Langen L, Sheldon R (2003) Immobilised enzymes: carrier-bound or carrier free? Curr Opin Biotech 14:387-394
Capellas M, Caminal G, Gonz ález G et al. (1996) Enzymic synthesis of a CCK-8 tripeptide frag-ment in organic media. Biotechnol Bioeng 50:700-708
Capellas M, Caminal G, Gonz ález G et al. (1997) Enzymatic condensation of cholecystokinin CCK-8 (4-6) and CCK-8 (7-8) peptide fragments in organic media. Biotechnol Bioeng 56 (4):456-463
Carrea G, Riva S (2000) Properties and synthetic applications of enzymes in organic solvents. Angew Chem Int Edit 39:2226-2254
Castro R (2000) Properties of soluble α-chymotrypsin in neat glycerol and water. Enzyme Microb Technol 27:143-150
Chan WC, White PD (2000) Fmoc solid phase peptide synthesis: a practical approach. Oxford University Press, Oxford, 341 pp
Chellapan S, Jasmin C, Basheer S et al. (2006) Production, purification and partial characterization of a novel protease from Engyodontium album BTMFS 10 under solid state fermentation. Proc Biochem 41:956-961
Clap és P, Mata-Alvarez J, Valencia G et al. (1989) Continuous enzymatic synthesis of Z-kyotorphin amide in an enzyme-immobilized fixed-bed reactor. J Chem Technol Biotechnol 45:191-202
Clap és P, Adlercreutz P, Mattiasson B (1990a) Enzymatic peptide synthesis in organic media: a comparative study of water-miscible and water-immiscible solvent systems. J Biotechnol 15 (4):323-338
Clap és P, Adlercreutz P, Mattiasson B (1990b) Enzymatic peptide synthesis in organic media: nu-cleophile specificity and medium engineering in α-chymotripsin-catalyzed reactions. Biotech-nol Appl Biochem 12:376-386
Clap és P, Caminal G, Feliu JA et al. (2000) Peptide synthesis in non-aqueous media. In: Gupta MN (ed). Methods in non-aqueous enzymology. Birkh äuser, Bassel, pp 110-132
Clap és P, Espelt L, Navarro M et al. (2001) Highly concentrated water-in-oil emulsions as novel reaction media for protease-catalysed kinetically controlled peptide synthesis. J Chem Soc Perk T 2:1394-1399
Clark D (2004) Characteristics of nearly dry enzymes in organic solvents: implications for bio-catalysis in the absence of water. Philos Trans R Soc London B 359:1299-1307
Du Vigneaud V, Ressler C, Swan J et al. (1953) The synthesis of an octapeptide amide with the hormonal activity of oxytocin. J Am Chem Soc 75:4879-4880
Ellman GL (1958) A colorimetric method for determining low concentrations of mercaptans. Arch Biochem Biophys 74:443-450
Feli ú J, De Mas C, L ópez-Santín J (1995) Studies on papain action in the synthesis of Gly-Phe in two-liquid-phase media. Enzyme Microb Technol 17:882-887
Filippova I, Lysogorskaya E (2003) Modified proteinases in peptide synthesis in organic media. Bioorg Khim 29(5):544-550
Fischer U, Zeitschel U, Jakubke H (1991) Chymotrypsin-catalyzed peptide synthesis in an acetonitrile-water-system: studies on the efficiency of nucleophiles. Biomed Biochim Acta 50 (10-11):S131-S135
Fit é M, Clap és P, L ópez-Santín J et al. (2002) Integrated process for the enzymatic synthesis of the octapeptide PhAcCCK-8. Biotechnol Progr 18:1214-1220
Floersheimer A, Kula M, Schuetz H et al. (1989) Continuous production of kyotorphin. Biotechnol Bioeng 33(11):1400-1405
Frank R (2002) The SPOT-synthesis technique. Synthetic peptide arrays on membrane supports: principles and applications. J Immunol Meth 267(1):13-26
Gill I, Valivety R (2002) Pilot-scale enzymatic synthesis of bioactive oligopeptides in eutectic-based media. Org Proc Res Develop 6(5):684-691
Gill I, López-Fandiño R, Vulfson E (1995) Enzymatic oligopeptide synthesis using a minimal protection strategy: sequential assembly of a growing oligopeptide chain. J Am Chem Soc 117 (23):6175-6177
Gill I, López-Fandiño R, Jorba X et al. (1996) Biologically active peptides and enzymatic ap-proaches to their production. Enzyme Microb Technol 18:162-183
Grunberg R, Domgall I, Gunther R et al. (2000) Peptide bond formation mediated by substrate mimetics. Eur J Biochem 267:7024-7030
Guis án J, Polo E, Aguado J et al. (1997) Immobilization-stabilization of thermolysin onto activated agarose gels. Biocatal Biotransfor 15:159-173
Guzm án F, Jaramillo K, Salazar LM et al. (2003) H-NMR structures of the Plasmodum falci-parum 1758 erythrocyte binding peptide analogues and protection against malaria. Life Sci 71 (23):2773-2785
Guzm án F, Barberis S, Illanes A (2007) Peptide synthesis: chemical or enzymatic. Electron J Biotechnol 10(2):279-314
Halling PJ (1994) Thermodynamic predictions for biocatalysis in nonconventional media: the-ory, tests, and recommendations for experimental design and analysis. Enzyme Microb Technol 16:178-206
Halling PJ, Eichhorn U, Khul P et al. (1995) Thermodynamics of solid-to-solid conversion and application to enzymic peptide synthesis. Enzyme Microb Technol 17:601-606
Hamel E, Covell DG (2002) Antimitotic peptides and depsipeptides. Curr Med Chem Anti-Cancer Agents 2(1):19-53
Hou R, Zhang N, Li G et al. (2005) Synthesis of the tripeptide RGD amide by a combination of chemical and enzymatic methods. J Mol Catal B: Enzym 37:9-15
Hou R, Yang Y, Huang Y et al. (2006a) Alcalase-catalyzed, kinetically controlled synthesis of a precursor dipeptide of RGDS in organic solvents. Prep Biochem Biotech 36(1):93-105
Hou R, Yang Y, Li G et al. (2006b) Synthesis of a precursor dipeptide of RGDS (Arg-Gly-Asp-Ser) catalysed by the industrial protease alcalase. Biotechnol Appl Biochem 44(2):73-80
Houghten RA (1985) General method for the rapid solid-phase synthesis of large numbers of pep-tides: specificity of antigen-antibody interaction at the level of individual amino acids. Proc Natl Acad Sci USA 82(15):5131-5135
Houghten RA, Wilson DB, Pinilla C (2000) Drug discovery and vaccine development using mixture-based synthetic combinatorial libraries. Drug Discov Today 5:276-285
Hudson E, Eppler, Clark D (2005) Biocatalysis in semi-aqueous and nearly anhydrous conditions. Curr Opin Biotech 16:637-643
Illanes A, Fajardo A (2001) Kinetically controlled synthesis of ampicillin with immobilized peni-cillin acylase in the presence of organic cosolvents. J Mol Catal B: Enzym 11(4-6):587-595
Illanes A, Wilson L (2003) Enzyme reactor design under thermal inactivation. Crit Rev Biotechnol 23 (1):61-93
Illanes A, Anjarí S, Altamirano C et al. (2004) Optimization of cephalexin synthesis with immobi-lized penicillin acylase in ethylene glycol medium at low temperatures. J Mol Catal B: Enzym 30:95-103
Jakubke H, Kuhl P, Konnecke A (1985) Basic principles of protease-catalyzed peptide bond for-mation. Angew Chem Int Edit 24:85-93
Johnson EC, Malito E, Shen Y et al. (2007) Insights from atomic-resolution X-ray structures of chemically synthesized HIV-1 protease in complex with inhibitors. J Mol Biol 373(3):573-586
Kasche V (1996) Proteases in peptide synthesis. In: Beynon R, Nond J (eds). Proteolytic enzymes -a practical approach. IRL Press, Oxford, pp 125-143
Kimmerlin T, Seebach D (2005) A100 years of peptide synthesis: ligation methods for peptide and protein synthesis with applications to β-peptide assemblies. J Pept Res 65:229-260
Kimura Y, Nakanishi K, Matsuno R (1990a) Enzymatic synthesis of precursor of Leu-enkephalin in water-immiscible organic solvent systems. Enzyme Microb Tech 12:272-280
Kimura Y, Muraya K, Araki Y et al. (1990b) Synthesis peptides consisting of essential amino acids by a reactor system using three proteinases and an organic solvent. Agr Biol Chem 54:3331-3333
Klibanov A (1997) Why are enzymes less active in organic solvents than in water? TIBTECH 15:97-101
Kumar D, Bhalla T (2005) Microbial proteases in peptide synthesis: approaches and applications. Appl Microbiol Biotechnol 68:726-736
Lei H, Chen L, Li X et al. (2004) The preparation of catalytically active papain immobilized on magnetic composite microspheres. Enzyme Microb Technol 35:15-21
Lioy E, Suarez J, Guzman F et al. (2001) Synthesis, biological, and immunological properties of cyclic peptides from Plasmodium falciparum merozoite surface protein-1. Angewand Chem Internat Ed 40(14):2631-2635
Liu P, Gui-Ling T, Kin-Sing L et al. (2002) Full enzymatic synthesis of a precursor of bioactive pentapeptide OGP (10-14) in organic solvents. Tetrahed Lett 43:2423-2425
Lloyd-Williams P, Giralt E (2000). Solid-phase convergent approaches to the synthesis of native peptides and proteins. In: Kates SA, Albericio F (eds). Solid-phase synthesis: a practical guide. Marcel Dekker, New York, pp 377-418
Lombard C, Saulnier J, Wallach J (2005) Recent trends in protease-catalyzed peptide synthesis. Protein Peptide Lett 12:621-629
Lou W, Zong M, Wu H (2004) Enhanced activity, enantioselectivity and stability of papain in asymmetric hydrolysis of D ,L-p-hydroxyphenylglycine methyl ester with ionic liquid. Biocatal Biotransform 22(3):171-176
Lu YA, Tam JP (2005) Peptide ligation by a reversible and reusable C-terminal thiol handle. Org Lett 7(22):5003-5006
Manabe K, Mori Y, Wakabayashi T et al. (2000) Organic synthesis inside particles in water: Lewis acid-surfactant-combined catalysts for organic reactions in water using colloidal dispersions as reaction media. J Am Chem Soc 122:7202-7207
Meng L, Joshi R, Eckstein H (2006) Application of enzymes for the synthesis of the cholecys-tokinin pentapeptide (CCK-5): a contribution to green chemistry. Chimica Oggi 24(3):50-53
Merrifield B (1963) Solid phase peptide synthesis. I. The synthesis of a tetrapeptide. J Am Chem Soc 85:2149-2154
Merrifield B (1986) Solid phase synthesis. Science 232:341-347
Merrifield B (1996) The chemical synthesis of proteins. Protein Sci 5:11947-11951
Mesiano A, Beckman E, Russell A (1999) Supercritical biocatalysis. Chem Rev 99:623-634
Miyazawa T, Nakajo S, Nishikawa M et al. (2001a) Chymotrypsin-catalysed peptide synthesis via the kinetically controlled approach using activated esters as acyl donors in organic solvents with low water content: incorporation of non-protein amino acids into peptides. J Chem Soc Perk 1:82-86
Miyazawa T, Tanaka K, Ensatsu E et al. (2001b) Broadening of the substrate tolerance of α-chymotrypsin by using the carbamoylmethyl ester as an acyl donor in kinetically controlled peptide synthesis. J Chem Soc Perk T 1 1:87-93
Murakami Y, Yoshida T, Hayashi S et al. (2000) Continuous enzymatic production of peptide precursor in aqueous/organic biphasic medium. Biotechnol Bioeng 69:57-65
Nakanishi K, Takeuchi A, Matsuno R (1990) Long term continuous synthesis of aspartame precur-sor in a column reactor with an immobilized thermolysin. Appl Microbiol Biot 32:633-636
Nardin EH, Calvo-Calle JM, Oliveira GA et al. (1998). Plasmodium falciparum polyoximes: highly immunogenic synthetic vaccines constructed by chemoselective ligation of repeat B-cell epi-topes and a universal T-cell epitope of CS protein. Vaccine 16:590-600
Nilsson B, Soellner M, Raines R (2005) Chemical synthesis of proteins. Annu Rev Biophys Biomol Struct 34:91-118
Obreg ón WD, Arrib ére MC, Morcelle Del Valle S et al. (2001) Two new cysteine endopeptidases obtained from the latex of Araujia hortorum fruits. J Protein Chem 20:317-325
Ogino H, Uchiho T, Yokoo J et al. (2001) Role of intermolecular disulfide bonds of the organic solvent stable PST-01 protease in its organic solvent stability. Appl Environ Microb 67:942-947
Park S, Kazlauskas R (2003) Biocatalysis in ionic liquids - advantages beyond green technology. Curr Opin Biotechnol 14:432-437
Patarroyo JH, Guzman F (2004) Peptideos sinteticos como vacinas. In: De Almeida MR, Borem A, Franco GR (eds). Biotecnologia e saude. Ed. Folha de Viçosa, Viçosa, pp 113-139
Patarroyo ME, Amador R, Clavijo P et al. (1988) A synthetic vaccine protects humans against challenge with asexual blood stages of Plasmodium falciparum malaria. Nature 332:158-161
Priolo N, Morcelle Del Valle S, Arrib ére MC et al. (2000) Isolation and characterization of cysteine protease from the latex of Araujia hortorum fruits. J Prot Chem 19:39-49
Quiroga E, Priolo N, Marchese J et al. (2005) Behaviour of araujiain, a new cystein phytoprotease, in organic media with low water content. Electron J Biotechnol 9:18-25
Quiroga E, Priolo N, Marchese J et al. (2006) Stability of araujiain, a novel plant protease, in different organic systems. Acta Farmacol Bonaer 24(2):204-208
Rance M, Sorensen OW, Bodenhausen G et al. (1983) Improved spectral resolution in cosy 1H NMR spectra of proteins via double quantum filtering. Biochem Biophys Res Commun 117 (2):479-485
Richards A, Gill I, Vulfson E (1993) Continuous enzymatic production of oligopeptides: synthesis of an enkephalin pentapeptide in a multistage bioreactor. Enzyme Microb Technol 15(11):928-935
Sarabia F, Chammaa S, Ruiz, AS et al. (2004) Chemistry and biology of cyclic depsipeptides of medicinal and biological interest. Curr Med Chem 11(10):1309-1332
Schmid A, Dordick J, Hauer B et al. (2001) Industrial biocatalysis today and tomorrow. Nature 409:258-268
Schwartz GJ, Netterville L, McHugh P et al. (1991) Gastric loads potentiate inhibition of food intake produced by a cholecystokinin analogue. Am J Physiol Reg 261(5 30-5):R1141-R1146
Schwarz A, Wandrey C, Steinke D et al. (1992) A two-step enzymatic synthesis of dipeptides. Biotechnol Bioeng 39(2):132-140
Sinisterra J, Alcantara A (1993) Synthesis of peptides catalyzed by enzymes: a practical overview. J Mol Catal 84(3):327-364
Stewart JM, Young JD (1984) Solid phase peptide synthesis, 2nd edn. Pierce Chemical Company, Rockford, 176 pp
Takagi H, Hirai K, Maeda Y et al. (2000) Engineering subtilisin E for enhanced stability and activity in polar organic solvents. J Biochem Tokyo 127:617-625
Tam JP, Heath WF, Merrifield B (1983) SN2 deprotection of synthetic peptides with a low con-centration of HF in dimethyl sulfide: evidence and application in peptide synthesis. J Am Chem Soc 105(21):6442-6456
Tam JP, Lu Y, Liu CF et al. (1995) Peptide synthesis using unprotected peptides through orthogonal coupling methods. Proc Natl Acad Sci USA 92(26):12485-12489
Thormann M, Thurst S, Hofmann H et al. (1999) Protease-catalyzed hydrolysis of substrate mimet-ics (inverse substrates): a new approach reveals a new mechanism. Biochemistry 38(19):6056-6062
Thurst S, Koksche B (2003) Protease-catalysed peptide synthesis for the site specific incorporation of alpha-fluoroalkyl amino acids into peptides. J Org Chem 68:2290-2296
Trusek-Holownia A (2003) Synthesis of Z-Ala-Phe.OMe, the precursor of bitter dipeptide in the two-phase ethyl acetate-water system catalysed by thermolysin. J Biotechnol 102:153-163
Tuchscherer G, Mutter M (1996) Template assisted protein de novo design. Pure Appl Chem 68 (11):2153-2162
van Unen D, Engbersen F, Reinhoudt D (1998) Large acceleration of α-chymotrypsin-catalyzed dipeptide formation by 18-crown-6 in organic solvents. Biotechnol Bioeng 59:553-556
van Unen D, Engbersen F, Reinhoudt D (2001) Studies on the mechanism of crown-ether-induced activation of enzymes in non-aqueous media. Biotechnol Bioeng 75:154-158
van Unen D, Engbersen F, Reinhoudt D (2002) Why do crown ethers activate enzymes in organic solvents. Biotechnol Bioeng 77:248-255
Villanueva M, Collins S, Jensen R et al. (1982) Structural requirements for action of cholecys-tokinin on enzyme secretion from pancreatic acini. Am J Phys 242(4):G416-422
Walsh G (2005) Therapeutic insulins and their large scale manufacture. Appl Microbiol Biotechol 67:151-159
West J, Hennen W, Lalonde J et al. (1990) Enzymes as synthetic catalysts: mechanistic and active-site considerations of natural and modified chymotrypsin. J Am Chem Soc 112:5313-5320
Wilson L, Illanes A, Abi án O et al. (2004a) Co-aggregation of penicillin G acylase and polyionic polymers: an easy methodology to prepare enzyme biocatalysts stable in organic media. Bio-macromolecules 5:852-857
Wilson L, Illanes A, Pessela B et al. (2004b) Encapsulation of crosslinked penicillin G acylase aggregates in Lentikats: evaluation of a novel biocatalyst in organic media. Biotechnol Bioeng 86:558-562
Xiang H, Xiang G, Lu Z et al. (2004) Total enzymatic synthesis of cholecystokinin CCK-5. Amino Acids 27(1):101-105
Yan LZ, Dawson PE (2001) Synthesis of peptides and proteins without cysteine residues by native chemical ligation combined with desulfurization. J Am Chem Soc 123(4):526-533
Yin H, Frederick KK, Liu D et al. (2006) Arylamide derivatives as peptidomimetic inhibitors of calmodulin. Org Lett 8(2):223-225
Zaks A, Dodds D (1997) Application of biocatalysis and biotransformations to the synthesis of pharmaceuticals. Drug Discov Today 2:513-531
Abian A, Wilson L, Mateo C (2002) Preparation of artificial hyper-hydrophilic micro-environments (polymeric salts) surrounding enzyme molecules. New enzyme derivatives to be used in any reaction medium. J Mol Catal B: Enzym 19-20:295-303
Abian A, Mateo C, Fern ández-Lorente G et al. (2003) Improving the industrial production of 6-APA: enzymatic hydrolysis of penicillin G in the presence of organic solvents. Biotechnol Prog 19:1639-1642
Abraham EP, Newton GGF (1961) The structure of cephalosporin C. Biochem J 79(2):377-393
Aguirre C, Toledo M, Medina V et al. (2002) Effect of cosolvent and pH on the kinetically con-trolled synthesis of cephalexin with immobilised penicillin acylase. Proc Biochem 38(3):351-360
Aharonowitz Y, Cohen G (1981) The microbiological production of pharmaceuticals. Scientific Amer 245(3):141-152
Alkema WB, de Vries E, Floris R et al. (2003) Kinetics of enzyme acylation and deacylation in the penicillin acylase-catalyzed synthesis of β-lactam antibiotics. Eur J Biochem 270:3674-3683
Alvaro G, Fern ández-Lafuente R, Blanco RM et al. (1990) Immobilization-stabilization of peni-cillin acylase from E. coli. Appl Biochem Biotech 26:186-195
Alvaro G, Fern ández-Lafuente R, Rosell CM et al. (1992) Penicillin G acylase from Kluyvera citrophila. New choice as industrial enzyme. Biotechnol Lett 14(4):285-290
Arroyo M, Torres-Guzm án R, de la Mata I et al. (2000) Activation and stabilization of penicillin V acylase from Streptomyces lavendulae in the presence of glycerol and glycols. Biotechnol Prog 16:368-371
Babu PSR, Panda T (1991) The role of phenylacetic acid in biosynthesis of penicillin amidase in E. coli. Bioproc Eng 6:71-74
Báez-Vásquez MA, Adrio JL, Piret JM et al. (1999) Further studies on the bioconversion of peni-cillin G into deacetoxycephalosporin G by resting cells of Streptomyces clavuligerus NP-1. Appl Biochem Biotechnol 81:145-152
Baldaro E (1991) Effect of temperature on enzymatic synthesis of cephalosporins. In: Pandit U (ed). Chemistry in healthcare and technology. Plenum Press, New York, pp 237-240
Basso A, Biffi S, De Martin L et al. (2001) Quantitative acylation of amino compounds catalysed by penicillin acylase in organic solvent at controlled water activity. Croatica Chem Acta 74(4):757-762
Basso A, De Martin L, Ebert C et al. (2003) Organically modified xerogels as novel tailor-made supports for covalent immobilisation of enzymes (penicillin G acylase). Tetrahed Lett 44:5889-5891
Basso A, Spizzo P, Toniutti M et al. (2006) Kinetically controlled synthesis of ampicillin and cephalexin in highly condensed systems in the absence of a liquid aqueous phase. J Mol Catal B: Enzym 39:105-111
Batchelor FR, Doyle FP, Nayler JHC et al. (1959) Synthesis of penicillin: 6-amino penicillanic acid in penicillin fermentations. Nature 183:257-258
Bruggink A (2001) Synthesis of β-lactam antibiotics. Kluwer Acad Publ, Dordrecht, 335 pp
Bruggink A, Roos EC, de Vroom E (1998) Penicillin acylase in the industrial production of β-lactam antibiotics. Org Proc Res Develop 2:128-133
Bryjak J, Trochimczuk AW (2006) Immobilization of lipase and penicillin acylase on hydrophobic carriers. Enzyme Microb Technol 39:573-578
Cao L, van Rantwijk F, Sheldon RA (2000) Cross-linked enzymes aggregates: a simple and effec-tive method for the immobilization of penicillin acylase. Org Lett 2:1361-1364
Cao L, van Langen LM, van Rantwijk F et al. (2001) Cross-linked aggregates of penicillin acylase: robust biocatalysts for the synthesis of β-lactam antibiotics. J Mol Catal B Enzym 11:665-670
Cao L, van Langen LM, Sheldon RA (2003) Immobilised enzymes: carrier-bound or carrier-free? Curr Opin Biotechnol 14:1-8
Chisti Y, Moo-Young M (1991) Fermentation technology, bioprocessing, scale-up and manufac-ture. In: Moses V, Cape RE (eds). Biotechnology: the science and the business. Harwood Aca-demic, New York, pp 167-209
Crawford L, Stepan PC, McAda JA et al. (1995) Production of cephalosporin intermediates by feeding adipic acid to recombinant Penicillium chrysogenum strains expressing ring expansion activity. Bio/Technology 13:58-62
de los Ríos AP, Hernández-Fernández FJ, Rubio M et al. (2007) Stabilization of native penicillin G acylase by ionic liquids. J Chem Technol Biotechnol 82:190-195
Demain A (1991) Production of beta-lactam antibiotics and its regulation. Proc Natl Sci Counc Repub China B 15(4):251-265
Demain A, Cho H, Piret JM et al. (2002) Penicillin conversion. US Patent 6383773. Issued on May 7,2002
Diender MB, Straathof AJ, Heijnen JJ (1998) Predicting enzyme catalyzed reaction equilibria in cosolvent-water mixtures as function of pH and solvent composition. Biocatal Biotransform 16:275-289
Diender MB, Straathof AJJ, van der Does T (2000) Course of pH during the formation of amoxi-cillin by a suspension-to-suspension reaction. Enzyme Microb Technol 27:576-582
Duggleby HJ, Tolley SP, Hill CP et al. (1995) Penicillin acylase has a single-amino-acid catalytic centre. Nature 373:264-268
Ebert C, Gardossi L, Linda P (1996) Control of enzyme hydration in penicillin acylase catalysed synthesis of amide bond. Tetrahed Lett 37(52):9377-9380
Elander RP (2003) Industrial production of β-lactam antibiotics. Appl Microbiol Biotechnol 61(5-6):385-392
Erbeldinger M, Ni X, Halling PJ (1998) Effect of water and enzyme concentration on thermolysin-catalyzed solid-to-solid peptide synthesis. Biotechnol Bioeng 59(1):68-72
Fern ández-Lafuente R, Alvaro G, Blanco RM et al. (1991) Equilibrium controlled synthesis of cephalotin in water-cosolvent systems by stabilized penicillin acylase. Appl Biochem Biotech-nol 27:277-289
Fern ández-Lafuente R, Rosell CM, Guisan JM (1995) The use of stabilized penicillin acylase derivatives improves the design of kinetically controlled synthesis. J Mol Catal A: Chemical 101:91-97
Fern ández-Lafuente R, Rosell CM, Guisan JM (1996a) Dynamic reaction design of enzymic bio-transformations in organic media: equilibrium-controlled synthesis of antibiotics by penicillin G acylase. Biotechnol Appl Biochem 24:139-143
Fern ández-Lafuente R, Rosell CM, Piatkowska B et al. (1996b) Synthesis of antibiotics (cephalo-glycin) catalyzed by penicillin G acylase: evaluation and optimization of different synthetic approaches. Enzyme Microb Technol 19:9-14
Fern ández-Lafuente R, Rosell CM, Guisan JM (1998) The presence of methanol exerts a strong and complex modulation of the synthesis of different antibiotics by immobilized penicillin G acylase. Enzyme Microb Technol 23:305-310
Fernandez-Lafuente R, Rosell C, Caanan-Haden L et al. (1999) Facile synthesis of artificial en-zyme nano-environments via solid-phase chemistry of immobilized derivatives: dramatic stabi-lization of penicillin acylase versus organic solvents. Enzyme Microb Technol 24:96-103
Ferreira JS, Straathof AJJ, Franco TT et al. (2004) Activity and stability of immobilized penicillin acylase at low pH values. J Mol Catal B: Enzym 27:29-35
Fit é M, Capellas M, Benaiges MD et al. (1997) N -protection of amino acid derivatives catalyzed by penicillin G acylase. Biocatal Biotransform 15:317-332
Fuganti C, Graselli P, Seneci PF et al. (1986) Immobilised benzylpenicillin acylase: application to the synthesis of optically active forms of carnitin and propanolol. Tetrahed Lett 27:2061-2062
Gabor EM, de Vries EJ, Janssen DB (2005) A novel penicillin acylase from the environmental gene pool with improved synthetic properties. Enzyme Microb Technol 36:182-190
Gavrilescu M, Chisti Y (2005) Biotechnology - a sustainable alternative for chemical industry. Biotechol Adv 23:471-499
Giordano RC, Ribeiro M, Giordano RL (2006) Kinetics of β-lactam antibiotics synthesis by penicillin acylase (PGA) from the viewpoint of the industrial enzymatic reactor optimization. Biotechnol Adv 24:27-41
Gonçalves LRB, Fern ández-Lafuente R, Guisan JM et al. (2000) A kinetic study of synthesis of amoxicillin using penicillin acylase immobilized on agarose. Appl Biochem Biotechnol 84-86:931-945
Gonçalves LR, Fern ández-Lafuente R, Guisan JM et al. (2002) The role of 6-aminopenicillanic acid on the kinetics of amoxicillin enzymatic synthesis catalyzed by penicillin G acylase immo-bilized onto glyoxyl agarose. Enzyme Microb Technol 31:464-471
Gorziglia G, Altamirano C, Conejeros R et al. (2002). Determination of kinetic parameters in the synthesis of ampicillin with immobilized penicillin acylase. Annals of the XV Chilean Congress of Chemical Engineering, Punta Arenas, October 2002, pp 107-112.
Guisan JM, Alvaro G, Fern ández-Lafuente R (1990) Immobilization-stabilization of penicillin G acylase. An integrated approach. Ann NY Acad Sci 613:552-559
Svedas VK (2004) PH stability of penicillin acylase from Escherichia coli. Biochem 69(12):1700-1705
Hernández-Jústiz O, Fernández-Lafuente R, Terreni M et al. (1998) Use of aqueous two-phase systems for in-situ extraction of water soluble antibiotics during their synthesis by enzymes immobilized on porous supports. Biotechnol Bioeng 59:73-79
Hernández-Jústiz O, Terreni M, Pagani G et al. (1999) Evaluation of different enzymes as catalysts for the production of β-lactam antibiotics following a kinetically controlled strategy. Enzyme Microb Technol 25:336-343
Hsu JS, Yang YB, Deng CH et al. (2004) Shuffling of expandase genes to enhance substrate speci-ficity for penicillin G. Appl Environ Microbiol 70(10):6257-6263
Hyun CK, Kim JH, Ryu DD (1993) Enhancement effect of water activity on enzymatic synthesis of cephalexin. Biotechnol Bioeng 42:800-806
Illanes A, Fajardo A (2001) Kinetically controlled synthesis of ampicillin with immobilized peni-cillin acylase in the presence of organic cosolvents. J Mol Catal B: Enzym 11:587-595.
Illanes A, Torres R, Cartagena O et al. (1993) Evaluation of penicillin acylase production by two strains of Bacillus megaterium. Biol Res 26:357-364
Illanes A, Acevedo F, Gentina JC et al. (1994) Production of penicillin acylase from Bacillus megaterium in complex and defined media. Proc Biochem 29(4):263-270
Illanes A, Wilson L, Tomasello G (2000) Temperature optimization for reactor operation with chitin-immobilized lactase under modulated inactivation. Enzyme Microb Technol 27:270-278
Illanes A, Anjarí S, Arrieta R et al. (2002) Optimization of yield in the kinetically controlled synthesis of ampicillin with immobilized penicillin acylase in organic media. Appl Biochem Biotechnol 97:165-179.
Illanes A, Cabrera Z, Wilson L et al. (2003) Synthesis of cephalexin in ethylene glycol with glyoxyl-agarose immobilised penicillin acylase: temperature and pH optimisation. Proc Biochem 39:111-117
Illanes A, Anjarí S, Altamirano C et al. (2004) Optimization of cephalexin synthesis with immobi-lized penicillin acylase in ethylene glycol medium at low temperatures. J Mol Catal B: Enzym 30:95-103
Illanes A, Altamirano C, Fuentes M et al. (2005a) Synthesis of cephalexin in organic medium at high substrate concentrations and low enzyme to substrate ratio. J Mol Catal B: Enzym 35:45-51
Illanes A, Rodríguez F, Bahamondes C et al. (2005b) Determination of lumped kinetic parame-ters and their thermal dependence for the synthesis of cephalexin with immobilized penicillin acylase in organic medium. Biochem Eng J 24:209-215
Illanes A, Wilson L, Caballero E et al. (2006) Crosslinked penicillin acylase aggregates for syn-thesis of β-lactam antibiotics in organic medium. Appl Biochem Biotechnol 133:189-202.
Illanes A, Wilson L, Altamirano C et al. (2007a) Production of cephalexin in organic medium at high substrates concentrations with CLEA of penicillin acylase and PGA-450. Enzyme Microb Technol 40:195-203
Illanes A, Wilson L, Corrotea O et al. (2007b) Synthesis of cephalexin with immobilized penicillin acylase at very high substrate concentrations in fully aqueous medium. J Mol Catal B: Enzym 47:72-78
Ishimura F, Seijo H (1991) Immobilization of penicillin acylase using porous polyacrilonitrile fibers. J Ferment Bioeng 71:140-143
Jager SAW, Jekel PA, Janssen DB (2007) Hybrid penicillin acylases with improved properties for synthesis of β-lactam antibiotics. Enzyme Microb Technol 40:1335-1344
Janssen MHA (2006) http://repository.tudelft.nl/file/200584/169747 ISBN:909020 7546
Jiang Y, Xia H, Guo C et al. (2007) Enzymatic hydrolysis of penicillin in mixed ionic liquids/water two-phase system. Biotechnol Prog 23:829-835
Kallenberg A, van Rantwijk F, Sheldon R (2005) Immobilization of penicillin G acylase: the key to optimum performance. Adv Synth Catal 347:905-926
Kasche V (1985) Ampicillin and cephalexin synthesis catalyzed by E. coli penicillin amidase. Yield increase due to substrate recycling. Biotechnol Lett 7(12):877-882
Kasche V (1986) Mechanism and yields in enzyme catalysed equilibrium and kinetically controlled synthesis of β-lactam antibiotics, peptides and other condensation products. Enzyme Microb Technol 8:4-16
Kemperman GJ, de Gelder FJ, Dommerholt PC et al. (1999) Clathrate-type complexation of cephalosporins with β-naphthol. Chem Eur J 5:2163-2168
Kheirolomoom A, Ardjmand M, Fazelina H et al. (2001) Clarification of penicillin acylase reaction mechanism. Proc Biochem 36:1095-1101
Kim MG, Lee SB (1996) Penicillin acylase-catalyzed synthesis of β-lactam antibiotics in water-methanol mixtures: effect of cosolvent content and chemical nature of substrate on reaction rates and yields. J Mol Catal B: Enzym 1:201-211
Kohsaka M, Demain AL (1976) Conversion of penicillin N to cephalosporin(s) by cell-free extracts of Cephalosporium acremonium. Biochem Biophys Res Commun 70(2):465-473
Koreishi M, Tani K, Ise Y et al. (2007) Enzymatic synthesis of β-lactam antibiotics and N -fatty-acylated amino compounds by the acyl transfer reaction catalyzed by penicillin V acylase from Streptomyces mobaraensis. Biosci Biotechnol Biochem 71(6):1582-1586
Kupka JY, Shen, YQ, Wolfe S et al. (1983) Partial purification and properties of the alpha-ketoglutarate-linked ring expansion enzyme of beta-lactam biosynthesis of Cephalosporium acremonium. FEMS Microbiol Lett 16:1-6
Kurochkina VB, Nys PS (2002) Kinetic and thermodynamic approach to design of processes for enzymatic synthesis of betalactams. Biocatal Biotransform 20(1):35-41
Lee SB, Ryu DDY (1982) Reaction kinetics and mechanism of penicillin amidase: a comparative study of computer simulation. Enzyme Microb Technol 4:35-38
Lin WJ, Kuo BY, Chou CP (2001) A biochemical engineering approach for enhancing production of recombinant penicillin acylase in Escherichia coli. Bioproc Biosys Eng 24:239-247
Lindsay JP, Clark DS, Dordick JS (2004) Combinatorial formulation of biocatalyst preparation for increased activity in organic solvents: salt activation of penicillin amidase. Biotechnol Bioeng 85 (5):553-560
Liu SL, Wei DZ, Song QX et al. (2006) Effect of organic cosolvent on kinetic resolution of tert-leucine by penicillin G acylase from Kluyvera citrophila. Bioproc Biosyst Eng 28:285-289
L ópez-Gallego F, Betancor L, Hidalgo A et al. (2004) Optimization of an industrial biocatalyst of glutaryl acylase: stabilization of the enzyme by multipoint covalent attachment onto new amino-epoxy Sepabeads. J Biotechnol 111:219-227
L ópez-Serrano P, Cao L, van Rantwijk F et al. (2002) Cross-linked enzyme aggregates with en-hanced activity: application to lipases. Biotechnol Lett 24:1379-1383
Lummer K, Rieks A, Galunsky B et al. (1999) PH dependence of penicillin amidase enantioselec-tivity for charged substrates. Biochim Biophys Acta 1433:327-334
Maeda K, Fang A, Demain AL et al. (1995) The substrate specificity of deacetoxycephalosporin C synthase (“expandase”) of Streptomyces clavuligerus is extremely narrow. Enzyme Microb Technol 17(3):231-234
Marín M, Gudiol F (2003). Antibi óticos betalact ámicos. Enferm Infecc Microbiol Clin 21(1):42-55
Martín L, Prieto MA, Cort és E et al. (1995) Cloning and sequencing of the pac gene encoding the penicillin G acylase of Bacillus megaterium ATCC 14945. FEMS Microbiol Lett 125(2-3):287-292
Mateles RI (1998) Penicillin: a paradigm for biotechnology. Candida Corp, Illinois, 114 pp
Mateo C, Palomo JM, van Langen L et al. (2004) A new mild cross-linking methodology to prepare cross-linked enzyme aggregates. Biotechnol Bioeng 86:273-276
Mateo C, Abian A, Bernedo M et al. (2005) Some special features of glyoxyl supports to immobi-lize proteins. Enzyme Microb Technol 37:456:462
Matsumoto K (1993) Production of 6-APA, 7-ACA and 7-ADCA by immobilized penicillin and cephalosporin amidases. In: Tanaka A, Tosa T, Kobayashi T (eds). Industrial application of immobilized biocatalysts. Marcel Dekker, New York, pp 67-88
McDougall B, Dunnill P, Lilly MD (1982) Enzymic acylation of 6-aminopenicillanic acid. Enzyme Microb Technol 4:114-115
Meevootisom V, Saunders J (1987) Cloning and expression of penicillin acylase genes from over-producing strains of Escherichia coli and Bacillus megaterium. Appl Microbiol Biotechnol 25:372-378
Michels PC, Khmelnitsky YL, Dordick JS et al. (1998) Combinatorial biocatalysis: a natural ap-proach to drug discovery. TIBTECH 16(5):210-215
Mislovi čova D, Mas árov á J, Bu čko M et al. (2006) Stability of penicillin acylase modified with various polysaccharides. Enzyme Microb Technol 39:579-585
Montes T, Graz ú V, Manso I et al. (2007) Improved stabilization of genetically modified peni-cillin G acylase in the presence of organic cosolvents by coimmobilization of the enzyme with polyethyleneimine. Adv Synth Catal 349:459-464
Nam DH, Kim C, Ryu DDY (1985) Reaction kinetics of cephalexin synthesizing enzyme from Xanthomonas citri. Biotechnol Bioeng 27:953-960
Newton GGF, Abraham EP (1955) Cephalosporin C, a new antibiotic containing sulphur and D-α-aminoadipic acid. Nature 175:548
Nierstrasz VA, Schro ën CGPH, Bosma R et al. (1999) Thermodynamically controlled synthesis of cefamandole. Biocatal Biotransform 17:209-223
Novella IS, Fargues C, Grevillot G (1994) Improvement of extraction of penicillin acylase by a combined use of chemical methods. Biotechnol Bioeng 44:379-382
Ospina S, L ópez-Munguía A, Gonz ález R et al. (1992) Characterization and use of a penicillin acylase biocatalyst. J. Chem Technol Biotechnol 53:205-214
Ospina SS, Merino E, Ramírez OT et al. (1995) Recombinant whole cell penicillin acylase bio-catalyst: production, characterization and use in the synthesis and hydrolysis of antibiotics. Biotechnol Lett 17:615-620
Ospina S, Barzana E, Ramírez OT (1996) Effect of pH in the synthesis of ampicillin by penicillin acylase. Enzyme Microb Technol 19:462-469
Ozturk DC, Kazan D, Erarslan A (2002) Stabilization and functional properties of Escherichia coli penicillinG acylase by covalent conjugation of anionic polysaccharide carboxymethyl cellulose. World J Microbiol Biotechnol 18:881-888
Pan JL, Syu MJ (2004) A thermal study on the use of immobilized penicillin G acylase in the formation of 7-amino-3-deacetoxy cephalosporanic acid from cephalosporin G. J Chem Technol Biotechnol 79(10):1050-1056
Pan JL, Syu MJ (2005) Kinetic study on substrate and product inhibitions for the formation of 7-amino-3-deacetoxy cephalosporanic acid from cephalosporin G by immobilized penicillin acylase. Biochem Eng J 23:203-210
Parmar A, Kumar H, Marwaha SS et al. (1998) Recent trends in the enzymatic conversion of cephalosporin C to 7-aminocephalosporanic acid (7-ACA). Critic Rev Biotechnol 18(1):1-12
Parmar A, Kumar H, Marwaha S et al. (2000) Advances in enzymatic biotransformation of penicillins to 6-aminopenicillanic acid (6-APA). Biotechnol Adv 18:289-301
Rajendhran J, Krishnakumar V, Gunasekaran P (2003) Production of penicillin G acylase from Bacillus sp: effect of medium components. World J Microbiol Biotechnol 19:107-110
Rajendhran J, Gunasekaran P (2004) Recent biotechnological interventions for developingim-proved penicillin G acylases. J Biosci Bioeng 97(1):1-13
Rajendhran J, Gunasekaran P (2007a) Application of cross-linked enzyme aggregates of Bacillus badius penicillin acylase for the production of 6-aminopenicillanic acid. Lett Appl Microbiol 44:43-49
Rajendhran J, Gunasekaran P (2007b) Molecular cloning and characterization of thermostable β-lactam acylase with broad substrate specificity from Bacillus badius. J Biosci Bioeng 103 (5):457-463
Ramírez OT, Zamora R, Espinoza G et al. (2004) Kinetic study of penicillin acylase production by recombinant E. coli in batch cultures. Proc Biochem 29:197-206
Rocchietti S, San Vicente-Urrutia A, Pregnolato M et al. (2002) Influence of the enzyme derivative preparation and substrate structure on the enantioselectivity of penicillin G acylase. Enzyme Microb Technol 31:88-93
Roche D, Prasad K, Repic O (1999) Enantioselective acylation of β-aminoesters using penicillin G acylase in organic solvents. Tetrahed Lett 40:3665-3668
Rolinson GN, Batchelor FR, Butterworth D et al. (1960) Formation of 6-aminopenicillanic acid from penicillin by enzymatic hydrolysis. Nat Lond 187:236-237
Rolinson GN, Geddes AM (2007) The 50th anniversary of the discovery of 6-aminopenicillanic acid (6-APA). Internatl J Antimicrob Agents 29:3-8
Rosell CM, Fern ández-Lafuente R, Guis án JM (1993) Resolution of racemic mixtures by synthesis reactions catalyzed by immobilized derivatives of the enzyme penicillin G acylase. J Mol Catal 84:365-371
Rosell CM, Terreni M, Fern ández-Lafuente R et al. (1998) A criterion for the selection of monophasic solvents for enzymatic synthesis. Enzyme Microb Technol 23:64-69
Roy JJ, Abraham TE (2004) Strategies in making cross-linked enzyme crystals. Chem Rev 104 (9):3705-3721
Schro ën CGP, Nierstrasz VA, Kroon PJ et al. (1999) Thermodynamically controlled synthesis of β-lactam antibiotics. Equilibrium concentrations and side-chain properties. Enzyme Microb Tech-nol 24:489-506
Schro ën CGPH, Nierstrasz VA, Moody HM et al. (2001a) Modelling of the enzymatic kinetic syn-thesis of cephalexin-influence of substrate concentration and temperature. Biotechnol Bioeng 73:171-178
Schro ën CGPH, Mohy Eldin MS, Janssen AE et al. (2001b) Cephalexin synthesis by immobi-lized penicillin acylase under non-isothermal conditions: reduction of diffusion limitation. J Mol Catal B: Enzym 15:163-172
Schro ën CGPH, Nierstrasz VA, Bosma R et al. (2002a) Integrated reactor concept for the enzymatic kinetic synthesis of cephalexin. Biotechnol Bioeng 80:144-154
Schro ën CGPH, Fretz CB, De Bruin VH et al. (2002b) Modelling of the enzymatic kinetically con-trolled synthesis of cephalexin. Influence of diffusional limitation. Biotechnol Bioeng 80:331-340
Senerovic L, Stankovic N, Spizzo P et al. (2005) High level production and covalent immobiliza-tion of Providencia rettgeri penicillin G acylase (PAC) from recombinant Pichia pastoris for the development of a novel and stable biocatalyst of industrial applicability. Biotechnol Bioeng 93 (2):344-354
Sheldon RA, van Rantwijk F, van Langen LM et al. (2001) Biocatalysts and biocatalysis in the syn-thesis of β-lactam antibiotics. In: Bruggink A (ed). Synthesis of β-lactam antibiotics. Kluwer Acad Publ, Dordrecht, pp 103-148
Shewale J, Sivaraman H (1989) Penicillin acylase: enzyme production and its application in the manufacture of 6-APA. Proc Biochem 24(4):146-154
Shewale J, Deshpande S, Sudhakaran V et al. (1990) Penicillin acylase: applications and potentials. Proc Biochem 26:97-103
Shewale JG, Sudhakaran V (1997) Penicillin V acylase: its potential in the production of 6-aminopenicillanic acid. Enz Microb Technol 20:402-410
Stapley EO, Jackson M, Hernandez S et al. (1972) Cephamycins, a new family of β-lactam antibi-otics I. Production by Actinomycetes, including Streptomyces lactamdurans sp. n1. Antimicrob Agents Chemother 2(3):122-131
Sudhakaran V, Desphande B, Ambedkar S et al. (1992) Molecular aspects of penicillin and cephalosporin acylases. Proc Biochem 27:131-143
Svedas VK, Savchenko MV, Beltser AI et al. (1996) Enantioselective penicillin acylase-catalyzed reactions. Ann NY Acad Sci 799:659-669
Terreni M, Pagani G, Ubiali D et al. (2001) Modulation of penicillin acylase properties via immo-bilization techniques: one-pot chemoenzymatic synthesis of cephamandole from cephalosporin C. Bioorg Med Chem Lett 11:2429-2432
Terreni M, Ubiali D, Pagani G et al. (2005) Penicillin G acylase catalyzed acylation of 7-ACA in aqueous two-phase systems using kinetically and thermodynamically controlled strate-gies: improved enzymatic synthesis of 7-[(1-hydroxy-1-phenyl)-sacetamido]-3acetoxymethyl-Δ3 -cephem-4-carboxylic acid. Enzyme Microb Technol 36:672-679
Travascio P, Zito E, de Maio A et al. (2002) Advantages of using non-isothermal bioreactors for the enzymatic synthesis of antibiotics: the penicillin G acylase as enzyme model. Biotechnol Bioeng 79:334-346
Ulijn RV, Janssen AEM, Moore BD et al. (2001) Predicting when precipitation-driven synthesis is feasible: applications to biocatalysis. Chem Eur J 7:2089-2098.
Ulijn RV, De Martin L, Halling PJ et al. (2002a) Enzymatic synthesis of β-lactam antibiotics via direct condensation. J Biotechnol 99(3):215-222
Ulijn RV, De Martin L, Gardossi L et al. (2002b) Solvent selection for solid-to-solid synthesis. Biotechnol Bioeng 80(5):509-515
Valle F, Balb ás P, Merino E et al. (1991) The role of penicillin amidases in nature and industry. Trends Biochem Sci 16:36-40
Vandamme E (1981) Use of microbial enzymes and cell preparations to synthesise oligopeptide antibiotics. J Chem Technol Biotechnol 31:637-659
van de Sandt EJ, de Vroom E (2000) Innovations in cephalosporin and penicillin production: paint-ing the antibiotics industry green. Chimica Oggi 18:72-75
van der Klein PAM, Castelijns J, Hirs HGJ et al. (1996) Ring expansion of norpenicillin to 3-norcephalosporin. Rec Trav Chim Pays-Bas 115:185-190
van der Weilken LA, Ottens M, Straathof JJ (2001) Process technology and process integration in the preparation of penicillins. In: Bruggink A (ed). Synthesis of β-lactam antibiotics. Kluwer Acad Publ, Dordrecht, pp 153-205
van Langen LM, Oosthoek NHP, Guranda DT et al. (2000) Penicillin acylase-catalyzed resolution of amines in aqueous organic solvents. Tetrahed Asymm 11:4593-4600
Verweij J, de Vroom E (1993) Industrial transformations of penicillins and cephalosporins. Recl Trav Chim Pays-Bas 112:66-81
Wang T, Zhu H, Ma X et al. (2006) Structure-based stabilization of an enzyme: the case of peni-cillin acylase from Alcaligenes faecalis. Prot Pept Lett 13:177-183
Wang Z, Wang L, Xu JH et al. (2007a) Enzymatic hydrolysis of penicillin G to 6-aminopenicillanic acid in cloud point system with discrete countercurrent experiment. Enzyme Microb Technol 41:121-126
Wang J, Zhang Q, Huang H et al. (2007b) Increasing synthetic performance of penicillin G acylase from Bacillus megaterium by site-directed mutagenesis. Appl Microbiol Biotechnol 74:1023-1030
Wegman M, Janssen M, van Rantwijk F et al. (2001) Towards biocatalytic synthesis of β-lactam antibiotics. Adv Synth Catal 343:559-576
Wegman MA, van Langen LM, van Rantwijk F et al. (2002) A two-step one-pot enzymatic syn-thesis of cephalexin from D-phenylglycine nitrile. Biotechnol Bioeng 79:356-361
Wei DZ, Zhu JH, Cao JX (2002) Enzymatic synthesis of cephalexin in aqueous two-phase systems. Biochem Eng J 11:95-99
Wei DZ, Yang L (2003) Effect of ethylene glycol on the synthesis of ampicillin using immobilized penicillin acylase. J Chem Technol Biotechnol 78:431-436
Wei D, Yang L, Song Q (2003) Effect of temperature on the enzymatic synthesis of cefaclor with in situ product removal. J Mol Catal B Enzym 26:99-104
Wilson L, Illanes A, Abian O et al. (2002) Encapsulation of very soft cross-linked enzyme aggre-gates CLEAs in very rigid LentiKats. FAL Agric Res 241:121-125
Wilson L, Illanes A, Abian O et al. (2004a) Co-aggregation of penicillin G acylase and polyionic polymers: an easy methodology to prepare enzyme biocatalysts stable in organic media. Bio-macromolecules 5:852-857
Wilson L, Illanes A, Pessela CB et al. (2004b) Encapsulation of crosslinked penicillin G acylase aggregates in Lentikats: evaluation of a novel biocatalyst in organic media. Biotechnol Bioeng 86 (5):558-562
Yang L, Wei Z (2003) Enhanced enzymatic synthesis of a semi-synthetic cephalosporin, cefaclor, with in situ product removal. Biotechnol Lett 25:1195-1198
Yang S, Zhou L, Tang H et al. (2002) Rational design of a more stable penicillin G acylase against organic cosolvent. J Mol Catal B Enzym 18:285-290
Yang Y, Biedendieck R, Wang W et al. (2006) High yield recombinant penicillin G amidase pro-duction and export into the growth medium using Bacillus megaterium. Microb Cell Fact 5:36
Svedas VK (2000) Kinetics of ampicillin synthesis catalyzed by penicillin acylase from E. coli in homogeneous and heterogeneous systems. Biochemistry (Moscow) 65:1367-1375
Svedas VK (2002) Penicillin acylase-catalyzed solid-state ampicillin synthesis. Adv Synth Catal 344(8):894-898
Youshko MI, van Langen LM, de Vroom E et al. (2000) Penicillin acylase-catalyzed synthesis of ampicillin in “aqueous solution-precipitate” system. High substrate concentration and supersat-uration effect. J Mol Catal B Enzym 10:509-515
Youshko MI, van Langen LM, de Vroom E et al. (2001) Highly efficient synthesis of ampicillin in an “aqueous solution precipitate” system: repetitive addition of substrates in a semicontinuous process. Biotechnol Bioeng 73: 426-430
Youshko MI, Chilov GG, Shcherbakova TA et al. (2002) Quantitative characterization of the nu-cleophile reactivity in penicillin acylase-catalyzed acyl transfer reaction. Biochim Biophys Acta 1599:134-140
Youshko MI, Bukhanov AL, Svedas VK (2003) Study of the nucleophile binding in the penicillin acylase active center. Kinetic analysis. Biochemistry (Moscow) 68(3):334-338
Youshko MI, Moody H, Bukhanov A et al. (2004) Penicillin acylase-catalyzed synthesis of β-lactam antibiotics in highly condensed aqueous systems: beneficial impact of kinetic substrate supersaturation. Biotechnol Bioeng 85:323-329
Zhang WG, Wei DZ, Yang XP et al. (2006) Penicillin acylase catalysis in the presence of ionic liquids. Bioproc Biosyst Eng 29:379-383
Zhang Y, Wei D, Li D et al. (2007) Optimisation of enzymatic synthesis of cefaclor with in situ product removal and continuous acyl donor feeding. Biocatal Biotransform 25(1):59-64
Aires-Barros MR, Cabral JMS (1991) Selective separation and purification of two lipases from Chromobacterium viscosum using AOT reversed micelles. Biotechnol Bioeng 38:1302-1307
Aires-Barros MR, Taipa MA, Cabral JMS (1994) Isolation and purification of lipases. In: Wooley P, Petersen SB (eds). Lipases - their structure, biochemistry and application. Cambridge University Press, Cambridge, pp 243-270
Alc ántara AR, Domínguez de María P, Fern ández M et al. (2004) Resolution of racemic acids, esters and amines by Candida rugosa lipase in slightly hydrated organic media. Food Technol Biotechnol 42(4):343-354
Allen LH (2000) Pitch control in pulp mills. In: Back EL and Allen LH (eds). Pitch control, wood resin and deresination. TAPPI Press, Norcross, pp 265-288
Alvarez L (2005) Immobilization of Alcaligenes sp. lipase QL for its use in the selective trans-esterification of stanols from a mixture of wood stanols and sterols. MSc Thesis, School of Biochemical Engineering, Universidad Cat ólica de Valparaíso, Valparaíso, 190 pp
Al-Zuhair S (2007) Production of biodiesel: possibilities and challenges. Biofuels Bioprod Bioref 1 (1):57-66
Anderson RE, Hedlund GB, Jensson V (1999) Thermal inactivation of a heat resistant lipase pro-duced by the psychrotrophic bacterium Pseudomonas fluorescens. J Dairy Sci 62:361-367
Ando M, Sanaka T, Nihei H (1999) Eicosapentanoic acid reduces plasma levels of remnant lipopro-teins and prevents in vivo peroxidation of LDL in dialysis patients. J Am Soc Nephrol 10:2177-2184
Archelas A, Furstoss R (1997) Synthesis of enantiopure epoxides through biocatalytic approaches. Annu Rev Microbiol 51:491-525
Arnold FH (2001) Combinatorial and computational challenges for biocatalyst design. Nature 409:253-257
Arroyo M, Sanchez-Montero JM, Sinisterra JV (1999) Thermal satabilization of immobilized li-pase B from C. antarctica on different supports: effect of water activity on enzymatic activity in organic media. Enzyme Microb Technol 24:3-12
Balcao VM, Paiva AL, Malcata FX (1996) Bioreactors with immobilized lipases: state of the art. Enzyme Microb Technol 18:392-398
Bandmann N, Collet E, Leijen J et al. (2000) Genetic engineering of the Fusarium solani pisi lipase cutinase for enhanced partitioning in PEG-phosphate aqueous two-phase system. J Biotechnol 79:161-172
Bastida A, Sabuquillo P, Armisen P et al. (1998) A single step purification, immobilization and hy-peractivation of lipases via interfacial adsorption on strongly hydrophobic supports. Biotechnol Bioeng 58:486-492
Beaton JM (1978) Preparation of sterol substrates for bioconversion. US Patent 4124607. Issued on November 7, 1978
Berglund P (2001) Controlling lipase enantioselectivity for organic synthesis. Biomol Eng 18: 13-22
Bloomer S, Adlercreutz P, Mattiasson B (1990) Triglyceride interesterification by lipases. Cocoa butter equivalents from a fraction of palm oil. JAOCS 67(8):519-524
Bornscheuer UT (2002) Methods to increase enantioselectivity of lipases and esterases. Curr Opin Biotechnol 13(6):543-547
Bradoo S, Saxena RK, Gupta R (1999) Two acidothermolerant lipases from new variants of Bacil-lus sp. World J Microbiol Biotechnol 15:87-91
Brady L, Brzozowski AM, Derewenda ZS et al. (1990) A serine protease triad forms the catalytic centre of a triacylglycerol lipase. Nature 343:767-770
Brzozowski AM, Derewenda U, Derewenda ZS et al. (1991) A model for interfacial activation in lipases from the structure of fungal lipase-inhibitor complex. Nature 351:491-494
Cameron PA, Davison BH, Frymier PD et al. (2002) Direct transesterification of gases by “dry” immobilized lipase. Biotechnol Bioeng 78(3):251-256
Cardenas J, Alvarez E, de Castro-Alvarez MS et al. (2001) Screening and catalytic activity in organic synthesis of novel fungal and yeast lipases. J Mol Catal B: Enzym 14:111-123
Cernia E, Palocci C, Soro (2000) Solvent engineering modulates stereoselectivity of microbial lipase. In: Alberghina L (ed). Protein engineering in industrial biotechnology. Harwood Acad-emic Publishers, Newark, pp 135-146
Cos O, Resina D, Ferrer P et al. (2005) Heterologous production of Rhizopus oryzae lipase in Pichia pastoris using the alcohol oxidase and formaldehyde dehydrogenase promoters in batch and fed-batch cultures. Biochem Eng J 26:86-94
Cowan D (1996) Industrial enzyme technology. TIBTECH 14:177-178
Cui Y, Wei D, Yu J (1997) Lipase-catalyzed esterification in organic solvent to resolve racemic naproxen. Biotechnol Lett 19:865-868
De Crescenzo G, Ducret A, Trani M et al. (2000) Enantioselective esterification of racemic keto-profen in non-aqueous solvent under reduced pressure. J Mol Catal B: Enzym 9(1-3):49-56
de Lathouder KM, Marques Fl ó T, Kapteijn F et al. (2005) A novel structured bioreactor: develop-ment of a monolithic stirrer reactor with immobilized lipase. Catal Today 105:443-447
de Oliveira D, Di Luccio M, Faccio C et al. (2004) Optimization of enzymatic production of biodiesel from castor oil in organic solvent medium. Appl Biochem Biotechnol 115(1-3):771-780
Demirjian DC, Moris-Varas F, Cassidy CS (2001) Enzymes from extremophiles. Curr Opin Chem Biol 5:144-151
Derewenda U, Brzozowski AM, Lawson DM et al. (1992) Catalysis at the interface: the anatomy of a conformational change in a trglyceride lipase. Biochemistry 31:1532-1541
Dong H, Gao S, Han S et al. (1999) Purification and characterization of a Pseudomonas sp. lipase and its properties in non aqueous media. Appl Microbiol Biotechnol 30:251-256
Donova MV, Dovbnya DV, Sukhodolskaya GV et al. (2004) Microbial conversion of sterol-containing soybean oil production waste. J Chem Technol Biotechnol 80(1):55-60
Dosanjh NS, Kaur J (2002) Immobilization, stability and esterification studies of a lipase from a Bacillus sp. Biotechnol Appl Biochem 36:7-12
Du W, Xu Y, Liu D et al. (2004) Comparative study on lipase-catalyzed transformation of soybean oil for biodiesel production with different acyl acceptors. J Mol Catal B: Enzym 30(3-4):125-129
Ducret A, Trani M, Lortie R (1998) Lipase catalysed enantioslective esterification of ibuprofen in organic solvent under controlled water activity. Enzyme Microb Technol 22:212-216
Elibol M, Ozer D (2001) Influence of oxygen transfer on lipase production by Rhizopus arrhizus. Proc Biochem 36:325-329
Faber K (1997) Biotransformations in organic chemistry. Springer, Berlin, Heidelberg, New York, 402 pp
Ferrer P, Montesinos JL, Valero F et al. (2001) Production of native and recombinant lipases by Candida rugosa: a review. Appl Biochem Biotechnol 95:221-255
Fregapane G, Sarney DB, Vulfson EN (1991) Enzymic solvent-free synthesis of sugar acetal fatty acid esters. Enzyme Microb Technol 13(10):796-800
Fuenzalida M, Markovits A, Martínez I (2006) Process for producing sterol or stanol esters by enzymatic transesterification in solvent and water free media. EP 1285969 B1. Issued on No-vember 10, 2006
Fujii R, Nakagawa Y, Hiratake J et al. (2005) Directed evolution of Pseudomonas aeruginosa lipase for improved amide-hydrolyzing activity. Protein Eng Des Sel 18(2):93-101
Fukuda H, Kondo A, Noda H (2001) Biodiesel fuel production by transesterification of oils. J Biosci Bioeng 92:406-416
Ghanem A, Aboul-Enein HY (2004) Lipase-mediated chiral resolution of racemates in organic solvents. Tetrahed Assym 15(21):331-3351
Ghanem A, Aboul-Enein HY (2005) Application of lipases in kinetic resolution of racemates. Chirality 17:1-15
Ghanem EH, Al-Sayeed HA, Saleh KM (2000) An alkalophilic thermostable lipase produced by a new isolate of Bacillus alcalophilus. World J Microbiol Biotechnol 16:459-464
Gotor V (2002) Lipases and (R)-oxynitrilases: useful tools in organic synthesis. J Biotechnol 96:35-42
Gulati R, Isar J, Kumar V et al. (2005) Production of a novel alkaline lipase by Fusarium globulo-sum using neem oil, and its applications. Pure Appl Chem 77(1):251-262
Gupta R, Gupta N, Rathi P (2004) Bacterial lipases: an overview of production, purification and biochemical properties. Appl Microbiol Biotechnol 64:763-781
Guti érrez A, del Río JC, Martínez J et al. (2001) The biotechnological control of pitch in paper pulp manufacturing. TIBTECH 19(9):340-348
Ha SH, Lan MN, Lee SH et al. (2007) Lipase-catalyzed biodiesel production from soybean oil in ionic liquids. Enzyme Microb Technol 41:480-483
Hari Krishna S, Karanth NG (2002) Lipases and lipase-catalyzed esterification reactions in non-aqueous media. Catal Rev 44(4):499-591
Hasan F, Shah AA, Hameed A (2006) Industrial applications of lipases. Enzyme Microb Technol 39:235-251
Hatti-Kaul R, T örnvall U, Gustafsson L et al. (2007) Industrial biotechnology for the production of bio-based chemicals - a cradle-to-grave perspective. TIBTECH 25(3):119-124
Henne A, Schmitez RA, Gottschalk G et al. (2000) Screening of environmental DNA libraries for the presence of genes conferring lipolytic activity on E. coli. Appl Environ Microbiol 66:3113-3116
Hilal N, Nigmatullin R, Alpatova A (2004) Immobilization of cross-linked lipase aggregates within microporous polymeric membranes. J Membrane Sci 238(1-2):131-141
Hiol A, Jonzo MD, Rugani N et al. (2000) Purification and characterization of an extracellular lipase from a thermophilic Rhizopus oryzae strain isolated from palm fruit. Enzyme Microb Technol 26:421-430
Hong MC, Chang MC (1998) Purification and characterization of an alkaline lipase from a newly isolated Acinetobacter radioresistens CMC-1. Biotechnol Lett 20:1027-1029
Hong Y, Wang TW, Hudak KA et al. (2000) An ethylene-induced cDNA encoding a lipase ex-pressed at the onset of senescence. Plant Biol 97:8717-8722
Houde A, Kademi A, Leblanc D (2004) Lipases and their industrial applications: an overview. Appl Biochem Biotechnol 118(1-3):155-170
Houssam ER, Perrard A, Pierre AC (2004) Application of lipase encapsulated in silica aerogels to a transesterification reaction in hydrophobic and hydrophilic solvents: bi-bi ping-pong kinetics. J Mol Catal B: Enzym 30(3-4):137-150
Hsu AF, Jones KC, Foglia TA et al. (2004) Transesterification activity of lipases immobilized in a phyllosilicate sol-gel matrix. Biotechnol Lett 26:917-921
Hung TC, Giridhar R, Chiou SH et al. (2003) Binary immobilization of Candida rugosa lipase on chitosan. J Mol Catal B: Enzym 26:69-78
Iso M, Chen B, Eguchi M et al. (2001) Production of biodiesel fuel from triglycerides and alcohol using immobilized lipase. J Mol Catal B: Enzym 16:53-58
Jaeger KE, Reetz MT (1998) Microbial lipases form versatile tools for biotechnology. TIBTECH 16:396-403
Jaeger KE, Dijkstra BW, Reetz MT (1999) Bacterial biocatalysts: molecular biology, three-dimensional structures and biotechnological applications of lipases. Annu Rev Microbiol 53:315-351
Jaeger KE, Eggert T, Eipper A et al. (2001) Directed evolution and the creation of enantioselective biocatalyst. Appl Microbiol Biotechnol 55:519-530
Jandacek RJ, Whiteside JA, Holcombe BN et al. (1987) The rapid hydrolysis and efficient absorp-tion of triglycerides with octanoic acid in the 1 and 3 positions and long-chain fatty acid in the 2 position. Am J Clin Nutr 45:940-945
Jensen RG (1983) Detection and determination of lipase (acylglycerol hydrolase) activity from various sources. Lipids 18:650-657
Jensen RG, Hamosh M (1996) Selectivity of lipases, types and determination. In: Malcata FK (ed). Engineering of/with lipases. Kluwer Academic Publishers, Dordrecht, pp 17-29
Johansson A (1982) By-product recovery and valorization in the kraft industry - a review of current trends in the recovery and use of turpentine and tall-oil derivatives. Biomass 2(2):103-113
Kamal A, Chouhan G (2004) Chemoenzymatic synthesis of enantiomerically pure 1,2-diols em-ploying immobilized lipase in the ionic liquid [bmim]PF6 . Tetrahed Lett 45:8801-8805
Kazlauskas RJ, Bornscheuer UT (1998) Biotransformations with lipases. In: Rehm HJ, Pihler G, Stadler A et al. (eds). Biotechnology, vol. 8. Wiley-VCH, New York, pp 37-192
Kirchner G, Scollar P, Klibanov AM (1985) Resolution of racemic mixtures via lipase catalysis in organic solvents. J Am Chem Soc 107:1012-1016
Klibanov AM (1997) Why are enzymes less active in organic solvents than in water? TIBTECH 15:97-101
Klibanov AM (2001) Improving enzymes by using them in organic solvents. Nature 409:241-246
Koeller KM, Wong CH (2001) Enzymes for chemical synthesis. Nature 409:232-240
Knothe G, van Gerpen J, Krahl J (2005) The biodiesel handbook. AOCS Press, Champaign, 304 pp
Koskinen AMP, Klibanov AM (1996) Enzymatic reactions in organic media. Blackie Academic Professional, London, 314 pp
Kovac A, Scheib H, Pleiss J et al. (2000) Molecular bases of lipase stereoselectivity. Eur J Lipid Sci Technol 102(1):61-77
Krishnakant S, Madamwar D (2001) Ester synthesis by lipase immobilized on silica and mi-croemulsion based organo-gels (MBGs). Proc Biochem 36:607-611
Kumari V, Shah S, Gupta MN (2007) Preparation of biodiesel by lipase-catalyzed transesterifica-tion of high free fatty acid containing oil from Madhuca indica. Energy Fuels 21(1):368-372
Laane C, Boeren S, Vos K et al. (1987) Rules for optimizaion of biocatalysis in organic solvents. Biotechnol Bioeng 30:81-87
Lalonde JJ, Govardhan C, Khalaf N et al. (1995) Crystals of Candida rugosa lipase: highly efficient catalyst for the resolution of chiral esters. J Am Chem Soc 117:6845-6849
Lau RM, Rantwijk FV, Seddon KR et al. (2000) Lipase-catalyzed reactions in ionic liquids. Org Lett 2:4189-4192
Laudani CG, Habulin M, Knez Zˇ et al. (2007) Immobilized lipase-mediated long-chain fatty acid esterification in dense carbon dioxide: bench scale packed-bed reactor study. J Supercrit Fluids 41:74-81
Lee OW, Koh YS, Kim KJ et al. (1999) Isolation and characterization of a thermophilic lipase from Bacillus thermoleovorans ID-1. FEMS Microbiol Lett 179:393-400
Lee SY, Hubbe MA, Saka S (2006) Prospects for biodiesel as a byproduct of wood pulping - a review. BioResources 1(1):150-171
Li X, Xu H, Wu Q (2007) Large-scale biodiesel production from microalga Chlorella protothe-coides through heterotrophic cultivation in bioreactors. Biotechnol Bioeng 98(4):764-771
Li ZY, Ward OP (1993) Enzyme catalysed production of vegetable oils containing omega-3 polyun-staurated fatty acid. Biotechnol Lett 15:185-188
Lichtenstein AH, Deckelbaum RJ (2001) Stanol/sterol ester-containing foods and blood cholesterol levels. Circulation 103:1177
Lieberman R, Ollis D (1975) Hydrolysis of particulate tributyrin in a fluidized lipase reactor. Biotechnol Bioeng 17:1401-1419
Linko YY, L äms ä M, Wu X et al. (1998) Biodegradable products by lipase biocatalysis. J Biotech-nol 66(1):41-50
Litthauer D, Ginster A, Skein EVE (2002) Pseudomonas luteola lipase: a new member of the 320-residue Pseudomonas lipase family. Enzyme Microb Technol 30:209-215
L ópez-Serrano P, Cao L, van Rantwijk F et al. (2002) Cross-linked enzyme aggregates with en-hanced activity: application to lipases. Biotechnol Lett 24:1379-1383
Lorenz P, Liebeton K, Niehaus (2002) Screening for novel enzymes for biocatalytic processes: ac-cessing the metagenome as a resource of novel functional sequence space. Curr Opin Biotechnol 13:572-577
Lowrier A, Drtina GJ, Klibanov AM (1996) On the issue of interfacial activation of lipase in nonaqueous media. Biotechnol Bioeng 50(1):1-5
Luo Y, Zheng Y, Jiang Z et al. (2006) A novel psychrophilic lipase from Pseudomonas fluorescens with unique property in chiral resolution and biodiesel production via transesterification. Appl Microbiol Biotechnol 73(2):349-355
Ma F, Hanna MA (1999) Biodiesel production: a review. Biores Technol 70:1-15
Magnusson A, Hult K, Holmquists M (2001) Creation of an enantioselective hydrolase by engi-neered substrate-assisted catalysis. J Am Chem Soc 123:4354-4355
Manjon A, Iborra JL, Arocas A (1991) Short-chain flavour ester synthesis by immobilized lipase in organic media. Biotechnol Lett 13:339-345
Margolin A (1996) Novel crystalline catalysts. TIBTECH 14:223-230
Markovits A, Chamy R, Illanes A et al. (2004) Upgrading of residues from Kraft cellulose process by the production of aromas, pharmaceuticals and nutraceuticals by enzyme biocatalysis. Final Report, Project FONDEF D00I 1096, CONICYT, Chile.
Martinelle M, Holmquist M, Hult K (1995) On the interfacial activation of Candida antarctica li-pase A and B as compared with Humicola lanuginose lipase. Biochim Biophys Acta 1258:272-276
Martínez I, Markovits A, Chamy R et al. (2004) Lipase-catalyzed solvent-free transesterification of wood sterols. Appl Biochem Biotechnol 112:55-62
Matsumoto T, Takahashi S, Kaieda M et al. (2001) Yeast whole-cell biocatalyst constructed by intracellular overproduction of Rhizopus oryzae lipase is applicable to biodiesel fuel production. Appl Microbiol Biotechnol 57(4):515-520
Maurer K (2004) Detergent proteases. Curr Opin Biotechnol 15:330-334
Misset O, Gerritse G, Jaeger KE et al. (1994) The structure-function relationship of the lipases from Pseudomonas aeruginosa and Bacillus subtilis. Protein Eng 7(4):523-529
Muralidhar RV, Chirumamilla RR, Marchant R et al. (2002) Understanding lipase stereoselectivity. World J Microbiol Biotechnol 18:81-97
Nakagawa Y, Hasegawa A, Hiratake J et al. (2007) Engineering of Pseudomonas aeruginosa li-pase by directed evolution for enhanced amidase activity: mechanistic implication for amide hydrolysis by serine hydrolases. Protein Eng Des Sel 20(7):339-346
Nardini M, Lang DA, Liebeton K et al. (2000) Crystal structure of Pseudomonas aeruginosa li-pase in the open conformation. The prototype for family L1 of bacterial lipases. J Biol Chem 275:31219-31225
Nguyen TT (1999) The cholesterol-lowering action of plant stanol esters. J Nutrit 129:2109-2112
Oh BC, Kim HK, Lee JK et al. (1999) Staphylococcus haemolyticus lipase: biochemical properties, substrate specificity and gene cloning. FEMS Microbiol Lett 179:385-392
Ollis DL, Shea E, Cygler M et al. (1992) The α/β hydrolase fold. Protein Eng 5:197-211
Omar IC, Hayashi M, Nagai S (1987) Purification and some properties of a thermostable lipase from Humicda lanuqinosa No 3. Agric Biol Chem 51(1):37-45
Ong AL, Kamaruddin AH, Bhatia S (2005) Current technologies for the production of (S)-ketoprofen: process perspective. Proc Biochem 40(11):3526-3535
Os ório NM, Gusm ão JH, da Fonseca MM et al. (2005) Lipase-catalysed interesterification of palm stearin with soybean oil in a continuous fluidised-bed reactor. Eur J Lipid Sci Technol 107(7-8):455-463
Ottonson J, Rotticci-Mulder JC, Rotticci D et al. (2001) Rational design of enantioselective en-zymes requires consideration of entropy. Protein Sci 10:1769-1774
Palekar AA, Vasudevan PT, Yan S (2000) Purification of lipase: a review. Biocatal Biotransform 18:177-200
Palomo JM, Fernandez-Lorente G, Mateo C et al. (2002) Modulation of the enantioselectivity of li-pases via controlled immobilization and medium engineering: hydrolytic resolution of mandelic acid esters. Enzyme Microb Technol 31:775-783
Palomo JM, Mu ñoz G, Fern ández-Lorente G et al. (2003) Modification of Mucor miehei lipase properties via directed immobilization on different heterofunctional epoxy resins. Hydrolytic resolution of (R,S)-2-butyroyl-2-phenylacetic acid. J Mol Catal B: Enzym 21:201-210
Palomo JM, Ortiz C, Fern ández-Lorente G et al. (2005) Lipase-lipase interaction as a new tool to immobilize and modulate the lipase properties. Enzyme Microb Technol 36:447-454
Park EY, Sato M, Kojima S (2006) Fatty acid methyl ester production using lipase-immobilizing silica particles with different particle sizes and different specific surface areas. Enzyme Microb Technol 39(4):889-896
Patklar SA, Bjorkling F (1994) Lipase inhibitors. In: Woolley P, Petersen SB (eds). Lipasetheir structure, biochemistry and application. Cambridge University Press, Cambridge, pp 207-224
P érez C, Falero A, Luu Duc H et al. (2006) A very efficient bioconversion of soybean phytosterols mixtures to androstanes by mycobacteria. J Ind Microbiol Biotechnol 33(8):719-723
Petkar M, Lali M, Caimi P et al. (2006) Immobilization of lipases for non-aqueous synthesis. J Mol Catal B: Enzym 39:83-90
Petrounia LP, Arnold FH (2000) Designed evolution of enzymatic properties. Curr Opin Biotechnol 11:325-330
Petschen I, Malo EA, Bosch MP et al. (1996) Highly enantioselective synthesis of long chain alkyl trifluormethyl carbinols and β-thiotrio-fluormethyl carbinols through lipases. Tetrahed Asymm 7:2135-2143
Pleiss J, Fisher M, Peiker M et al. (2000) Lipase engineering database. Understanding and exploit-ing sequence-structure-function relationships. J Mol Catal B: Enzym 10:491-508
Plou, FJ, Cruces, MA, Ferrer, M et al. (2002) Enzymatic acylation of di- and trisaccharides with fatty acids: choosing the appropriate enzyme, support and solvent. J Biotechnol 96:55-66
Pope LE, Khalil, MH, Marcelletti JF (1999) Treatment of hyperproliferative skin disorders with C18 to C26 alphatic alcohols. US Patent 5948822. Issued on July 9, 1999
Queiroz JA, Garcia FAP, Cabral JMS (1995) Hydrophobic interaction chromatography of Chro-mobacterium viscosum lipase. J Chromatogr A 707:137-142
Queiroz JA, Tomaz CT, Cabral JMS (2001) Hydrophobic interaction chromatography of proteins. J Biotechnol 87:143-159
Rashid N, Shimada Y, Ekazi S et al. (2001) Low-temperature lipase from psychrotropic Pseudomonas sp. strain KB700A. Appl Environ Microbiol 67:4064-4069
Rathi P, Saxena RK, Gupta R (2001) A novel alkaline lipase from Burkholderia cepacia for deter-gent formulation. Proc Biochem 37:187-192
Reetz MT, Zonta A, Simpelkamp J (1996) Efficient immoblization of lipases by entrapment in hydrophobic sol-gel materials. Biotechnol Bioeng 49:527-534
Reetz MT (2001) Combinatorial and evolution-based methods in the creation of enantioselective catalyst. Angew Chem Int Ed 40: 284-310
Reetz MT (2002) Lipases as practical biocatalysts. Curr Opin Chem Biol 6(2):145-150
Reyes HR, Hill CG, Amundson CH (1994) Interesterification reactions catalyzed by a lipase im-mobilized on a hydrophobic support. J Food Proc Preserv 18(2):119-132
Roberts SM (1998) Preparative biotransformations: the employment of enzymes and whole-cells in synthetic organic chemistry. J Chem Soc Perkin Trans 1:157-170
Roberts SM, Williamson NM (1997) Use of enzymes for the preparation of biologically active natural products and analogues in optically active form. Curr Org Chem 1:1-20
Rotticci D, Rotticci-Mulder JC, Denman S et al. (2001) Improved enantioselectivity of a lipase by rational protein engineering. Chem Bio Chem 2:766-770
Royon D, Daza M, Ellenrieder G et al. (2007) Enzymatic production of biodiesel from cotton seed oil using t -butanol as a solvent. Biores Technol 98(3):648-653
Rubin B, Dennis EA (1997) Lipases part B. Enzyme characterization and utilization. Methods in Enzymology, vol. 286. Academic Press, San Diego, 563 pp
Salis A, Sanjust E, Solinas V et al. (2003) Characterisation of Accurel MP1004 polypropylene powder and its use as a support for lipase immobilization. J Mol Catal B: Enzym 24-25: 75-82
Salis A, Monduzzi M, Solinas V (2007) Use of lipases for the production of biodiesel. In: Po-laina J, Mac Cabe AP (eds). Industrial enzymes structure, function and applications. Springer, Netherlands, pp 317-339
Saxena RK, Ghosh PK, Gupta R et al. (1999) Microbial lipases: potential biocatalysts for the future industry. Curr Sci 77:101-115
Saxena RK, Sheoran A, Giri B et al. (2003) Purification strategies for microbial lipases. J Microbiol Meth 52:1-18
Schmidt-Dannert C (1999) Recombinant lipases for biotechnological applications. Bioorg Med Chem 7:2123-2130
Schoevaart R, Wolbers MW, Golubovic M et al. (2004) Preparation, optimization and structures of cross-linked enzyme aggregates (CLEAs). Biotechnol Bioeng 87:754-762
Schulz T, Plesis J, Schmid RD (2000) Stereoselectivity of Pseudomonas cepacia lipase toward secondary alcohols: a quantitative model. Protein Sci 9:1053-1062
Secundo F, Carrea, G, Tarabiono C et al. (2006) The lid is a structural and functional determinant of lipase activity and selectivity. J Mol Catal B: Enzym 39:166-170
Seitz EW (1974) Industrial application of microbial lipases: a review. JAOCS 51(2):12-16
Sharma R, Chisti Y, Banerjee UC (2001) Production, purification, characterization and application of lipases. Botechnol Adv 19:627-662
Sharma R, Soni SK, Vohra RM et al. (2002) Production of extracellular alkaline lipase from a Bacillus sp. RSJ1 and its application in ester hydrolysis. Ind J Microbiol 42:49-54
Sharon C, Furugoh S, Yamakido T et al. (1998) Purification and characterization of a lipase from Pseudomonas aeruginosa KKA-5 and its role in castor oil hydrolysis. J Ind Microbiol Biotech-nol 20:304-307
Shibamoto H, Matsumoto T, Fukuda H et al. (2004) Molecular engineering of Rhizopus oryzae lipase using a combinatorial protein library constructed on the yeast cell surface. J Mol Catal B: Enzym 28(4-6):235-239
Shimada Y, Watanabe Y, Sugihara A et al. (2002) Enzymatic alcoholysis for biodiesel fuel produc-tion and application of the reaction to oil processing. J Mol Catal B: Enzym 17(3-5):133-142
Smith LC, Faustinella F, Chan L (1992) Lipases: three dimensional structure and mechanism of action. Curr Opin Struct Biol 2:490-496
Soares CMF, De Castro HF, Santana MHA et al. (2002) Intensification of lipase performance for long-term operation by immobilization on controlled pore silica in presence of polyethylene glycol. Appl Biochem Biotechnol 98-100:863-874
Soumanou MM, Bornschener UT, Menge U (1997) Synthesis of structured triglycerides from peanut oil with immobilized lipase. JAOCS 74:427-433
Soumanou MM, Bornscheuer UT (2003) Improvement in lipase-catalyzed synthesis of fatty acid methyl esters from sunflower oil. Enzyme Microb Technol 33(1):97-103
Straathof AJJ, Panke S, Schmid A (2002) The production of fine chemicals by biotransformations. Curr Opin Biotechnol 13:548-556
Sugihara A, Tani T, Tominaga Y (1991) Purification and characterization of a novel thermostable lipase from Bacillus sp. J Biochem 109:211-216
Sunitha S, Kanjilal S, Reddy PS (2007) Ionic liquids as reaction medium for lipase-catalyzed methanolysis of sunflower oil. Biotechnol Lett 29:1881-1885
Sunna A, Hunter L, Hutton C et al. (2002) Biochemical characterization of a recombinant ther-moalkalophilic lipase and assessment of its substrate enantioselectivity. Enzyme Microb Tech-nol 31:472-476
Svendsen A (2000) Lipase protein engineering. Biochim Biophys Acta 1543:223-238
Taipa MA, Aires-Barros MR, Cabral JMS (1992) Purification of lipases. J Biotechnol 26:111-142
Takagi Y, Teramoto J, Kihara H et al. (1996) Thiacrown ether as regulator of lipase-catalyzed trans-sterification in organic media - practical optical resolution of allyl alcohols. Tetrahed Lett 37:4991-4992
Terstappen GC, Gerts AJ, Kula MR (1992) The use of detergent-based aqueous two phase systems for the isolation of extracellular proteins: purification of a lipase from Pseudomonas cepacia. Biotechnol Appl Biochem 16:228-235
Thompson CA, Delaquis PJ, Mazza G (1999) Detection and measurement of microbial lipase activity: a review. Critic Rev Food Sci Nutr 39(2):165-187
Tobin MB, Gustafsson C, Huisman GW (2000) Directed evolution: the ‘rational’ basis for ‘irra-tional’ design. Curr Opin Struc Biol 10:421-427
Tombs MP (1995) Enzymes in the processing of fats and oils. In: Tucker GA, Woods LFJ (eds). Enzymes in food processing. Blackie Academic Professional, London, UK, pp 268-291
Tombs MP, Blake GG (1982) Stability and inhibition of Aspergillus and Rhizopus lipases. Biochim Biophys Acta 700:81-89
Undurraga D, Markovits A, Erazo S (2001) Cocoa butter equivalent through enzymic interesterifi-cation of palm oil midfraction. Proc Biochem 36:933-939
van Gerpen J (2005) Biodiesel processing and production. Fuel Proc Technol 86(10):1097-1107
van Kappen MD, Egmond MR (2000) Directed evolution: from a staphyloccal lipase to a phos-pholipase. Eur J Lipid Sci Technol 102:717-726
van Tilbeurgh H, Egloff MP, Martinez C et al. (1993) Interfacial activation of the lipase-procolipase complex by mixed micelles revealed by X-ray crystallography. Nature 362: 814-820
Verger R (1997) Interfacial activation of lipases: facts and artifacts. TIBTECH 15:32-38
Vicente MLC, Aires-Barros MR, Cabral JMS (1990) Purification of Chromobacterium viscosum lipases using reverse micelles. Biotechnol Techn 4:137-142
Villeneuve P, Muderhwa JM, Graille J et al. (2000) Customizing lipases for biocatalysis: a survey of chemical, physical and molecular approaches. J Mol Catal B: Enzym 9:113-148
Vulfson EN (1994) Industrial applications of lipases. In: Woolley P, Peterson SB (eds). Lipases: their structure, biochemistry and applications. Cambridge University Press, Cambridge, pp 271-288
Wang Y, Srivastava KC, Shen GJ et al. (1995) Thermostable alkaline lipase form a newly isolated Bacillus strain, A30-1 (ATCC 5384). J Ferment Bioeng 79:433-438
Wasserscheid P, Keim W (2000) Ionic liquids - new “solutions” for transition metal catalysis. Angew Chem 39(21):3772-3789
Watanabe K, Ueji SI (2001) Dimethyl sulfoxide as a co-solvent dramatically enhances the enan-tioselectivity in lipase-catalysed resolutions of 2-phenoxypropionic acyl derivatives. J Chem Soc Perkin Trans 1:1386-1390
Wehtje E, Adlercreutz (1997) Water activity and substrate concentration effects on lipase activity. Biotechnol Bioeng 55:798-806
Wilson L, Fern ández-Lorente G, Fern ández-Lafuente R et al. (2006) CLEAs of lipases and poly-ionic polymers: a simple way of preparing stable biocatalysts with improved properties. Enzyme Microb Technol 39:750-755
Wiseman A (1995) Introduction to principles. In: Wiseman A (ed). Handbook of enzyme biotech-nology, 3rd edn. Ellis Horwood Ltd, Cornwall, pp 3-8
Xin JY, Li SB, Xu Y et al. (2001) Dynamic enzymatic resolution of naproxen methyl ester in a membrane bioreactor. J Chem Technol Biotechnol 76(6):579-585
Xu X, Balchen S, Jonsson GA et al. (2000) Production of structured lipids by lipase-catalyzed interesterification in a flat membrane reactor. J Am Oil Chem Soc 77:1035-1041
Yadav GD, Devi KM (2004) Immobilized lipase-catalysed esterification and transesterification reactions in non-aqueous media for the synthesis of tetrahydrofurfuryl butyrate: comparison and kinetic modeling. Chem Eng Sci 59(2):373-383
Yamada H, Sorimachi Y, Tagawa T (2007) Operation optimization of lipase-catalyzed biodiesel production. J Chem Eng Japan 40(7):571-574
Yu H, Wu J, Ching CB (2004) Kinetic resolution of ibuprofen catalyzed by Candida rugosa lipase in ionic liquids. Chirality 17(1):16-21
Yu HW, Chen H, Wang X et al. (2006) Cross-linked enzyme aggregates (CLEAs) with controlled particles: application to Candida rugosa lipase. J Mol Catal B: Enzym 43(1-4):124-127
Zaks A, Klibanov AM (1988) Enzymatic catalysis in non-aqueous solvents. J Biol Chem 263:3192-3196
Bi Y, Zhou M, Hu H et al. (2001) Oxidation of long chain primary alcohols to acids over the quaternary ammonium peroxotungstophosphate catalyst system. React Kin Catal 72(1):73-82
Bommarius AS, Drauz K, Hummel W et al. (1994) Some new developments in reductive amination with cofactor regeneration. Biocatal Biotransform 10:37-47
Chenault HK, Simon ES, Whitesides GM (1988) Cofactor regeneration for enzyme-catalysed syn-thesis. Biotechnol Gen Eng Rev 6:221-241
Clymer J (2006). Composiciones y m étodos para el tratamiento de enfermedades gastrointestinales. Patente Mexicana No. 06001477 A.
Devaux-Basseguy R, Bergel A, Comtat M (1997) Potential applications of NAD(P)-dependent oxidoreductases in synthesis: a survey. Enzyme Microb Technol 20:248-258
El-Zahab B, Donnelly D, Wang P (2008) Particle-tethered NADH for production of methanol from CO2 catalyzed by coimmobilized enzymes. Biotechnol Bioeng 99(3):508-514
Godjevargova T, Dayal R, Turmanova S (2004) Gluconic acid production in bioreactor with immo-bilized glucose oxidase plus catalase on polymer membrane adjacent to anion-exchange mem-brane. Macromol Biosci 4:950-956
Hirakawa H, Kamiya N, Kawarabayashi Y et al. (2004) Properties of an alcohol dehydrogenase from the hyperthermophilic Archaeon Aeropyrum pernix K1. J Biosci Bioeng 97(3):202-206
Hummel W (1990) Enzyme-catalyzed synthesis of optically pure R(+)-phenylethanol. Biotechnol Lett 12:403-408
Hummel W (1997) New alcohol dehydrogenases for the synthesis of chiral compounds. Adv Biochem Eng Biotechnol 58:145-184
Hummel W (1999) Large-scale applications of NAD(P)-dependent oxidoreductases: recent devel-opments. TIBTECH 17:487-492
Hummel W, Kula M (1989) Dehydrogenases for the synthesis of chiral compounds. Eur J Biochem 184:1-13
Hummel W, Sch ütte H, Kula MR (1985) D-2-Hydroxyisocaproate dehydrogenase from Lactobacil-lus casei. A new enzyme suitable for stereospecific reduction of 2-ketocarboxylic acids. Appl Microbiol Biotechnol 21:7-15
Kawakami K, Nagamatsu S, Ishii M et al. (1986) Enzymatic formation of propylene bromohydrin from propylene by glucose oxidase and lactoperoxidase. Biotechnol Bioeng 28: 1007-1013
Kim MJ, Whitesides GM (1988) L-lactate dehydrogenase: substrate specificity and use as a catalyst in the synthesis of homochiral 2-hydroxy acids. J Am Chem Soc 110:2959-2962
Kobayashi S, Higashimura H (2003) Oxidative polymerization of phenols revisited. Prog Polym Sci (Oxford) 28:1015-1048
Lin C, Yang MC (2003) Cholesterol oxidation using hollow fiber dialiyser immobilised with cholesterol oxidase: preparation and properties. Biotechnol Prog 19:361-364
Liu W, Wang P (2007) Cofactor regeneration for sustainable enzymatic biosynthesis. Biotechnol Adv 25(4):369-384
L ópez-Gallego F, Betancor L, Hidalgo A et al. (2005) Preparation of a robust biocatalyst of D-amino acid oxidase on Sepabeads supports using the glutaraldehyde crosslinking method. En-zyme Microb Technol 37(7):750-756
Maekawa M (1995) Properties of enzymes for enzyme immunoassay. Nippon Rinsho. Japan J Clin Med 53:2154-2159
Malherbe D F, du Toit M, Cordero-Otero R et al. (2003) Expression of the Aspergillus niger glucose oxidase gene in Saccharomyces cerevisiae and its potential applications in wine production. Appl Microbiol Biotechnol 61:502-511
Nielsen J, Raschke T, Riedel H (2005) Cosmetic and dermatological preparations in the form of o/ω-emulsions containing sterols and/or C12-C40 fatty acids. US Patent 0037036
Al Pilone M S, Pollegioni L (2002) D-amino acid oxidase as an industrial biocatalyst. Biocatal Bio-transform 20:145-159
Tishkov VI, Popov VO (2004) Catalytic mechanism and application of formate dehydrogenase. Biochemistry (Moscow) 69:1252-1267
van der Donk WA, Zhao H (2003) Recent developments in pyridine nucleotide regeneration Cur-rent Opin Biotechnol 14:421-426
Vasic-Racki D, Jonas M, Wandrey C et al. (1989) Continuous (R)-mandelic acid production in an enzyme membrane reactor. Appl Microbiol Biotechnol 31:215-222
Wilson R, Clavering C, Hutchinson A (2003) Paramagnetic bead based enzyme electrochemilumi-nescence immunoassay for TNT. J Electroanal Chem 557(15):109-118
Yoshiro M. (2001) Lubricant for medicine or candy tablet. Japanese Patent 055342
Antonietti M (2001) Surfactants for novel templating applications. Curr Opin Colloid Interface Sci 6:244-248
Ardao I, Benaiges MD, Caminal G et al. (2006) One step purification-immobilization of fuculose-1-phosphate aldolase, a class II dependent aldolase, by using metal-chelate supports. Enzyme Microb Technol 39:22-27
Asano N, Nash RJ, Molyneux RJ et al. (2000) Sugar-mimic glycosidase inhibitors: natural occur-rence, biological activity and prospects for therapeutic application. Tetrahed Asymm 11:1645-1680
Azema L, Bringaud F, Blonski C et al. (2000) Chemical and enzymatic synthesis of fructose ana-logues as probes for import studies by the hexose transporter in parasites. Bioorg Med Chem 8:717-722
Babu YS, Chand P, Bantia S et al. (2000) Bcx-1812 (rwj-270201): discovery of a novel, highly potent, orally active, and selective influenza neuraminidase inhibitor through structure-based drug design. J Med Chem 43:3482-3486
Budde CL, Khmelnitsky YL (1999) Aldolase stability in the presence of organic solvents. Biotech-nol Lett 21:77-80
Calveras J, Bujons J, Parella T et al. (2006) Influence of N -amino protecting group on aldolase-catalyzed aldol additions of dihydroxyacetone phosphate to amino aldehydes. Tetrahedron 62:2648-2656
Castillo JA, Calveras J, Casas J et al. (2006) Fructose-6-phosphate aldolase in organic synthesis: preparation of D-fagomine, N -alkylated derivatives, and preliminary biological assays. Org Lett 8:6067-6070
Chen L, Dumas DP, Wong CH (1992) Deoxyribose 5-phosphate aldolase as a catalyst in asymmet-ric aldol condensation. J Am Chem Soc 114:741-748
Chenevert R, Dasser M (2000) Chemoenzymatic synthesis of the microbial elicitor-(-)syringolide via a fructose 1,6-diphosphate aldolase-catalyzed condensation reaction. J Org Chem 65:4529-4531
Clap és P, Espelt L, Navarro MA et al. (2001) Highly concentrated water-in-oil emulsions as novel reaction media for protease-catalyzed kinetically controlled peptide synthesis. J Chem Soc Perkin Trans 2:1394-1399
Dreyer MK, Shulz GE (1996) Refined high resolution structure of the metal-ion dependent L-fuculose-1-phosphate aldolase (Class II) from E. coli. Acta Crystallogr D 52:1082-1091
De Santis G, Liu JJ, Clark DP et al. (2003) Structure-based mutagenesis approaches toward ex-panding the substrate specificity of D-2-deoxyribose-5-phosphate aldolase. Bioorg Med Chem 11:43-52
Durany O, de Mas C, L ópez-Santín J (2005) Fed-batch production of recombinant fuculose-1-phosphate aldolase in E. coli. Proc Biochem 40:707-716
Espelt L, Clap és P, Esquena J et al. (2003a) Enzymatic carbon-carbon bond formation in water-in-oil highly concentrated (gel emulsions). Langmuir 19:1337-1346
Espelt L, Parella T, Bujons J et al. (2003b) Stereoselective aldol additions catalyzed by dihydrox-yacetone phosphate dependent aldolases in emulsion systems. Chem Eur J 9:4887-4899
Espelt L, Bujons J, Parella T et al. (2005) Aldol additions of dihydroxyacetone phosphate to N -Cbz-amino aldehydes catalyzed by L-fuculose-1-phosphate aldolase in emulsion systems: in-version of stereoselectivity as a function of the acceptor aldehyde. Chem Eur J 11:1392-1401
Fessner WD, Sinerius G, Schneider A et al. (1991) Enzymes in organic synthesis. Part I. Diastere-oselectivity, enzymatic aldol addition with L-rhamnulose and L-fuculose-1-phosphate aldolases from E. coli. Angew Chem Int Ed Engl 30:555-58
Fessner WD, Walter CH (1997) Enzymatic C C bond formation in asymmetric synthesis. Top Curr Chem 184:97-194
Fessner WD (1998) Enzyme mediated C C bond formation. Curr Opin Chem Biol 2:85-97
Fessner WD (2000) Enzymatic asymmetric synthesis using aldolases. In: Patel RN (ed). Stereose-lective biocatalysis. Marcel Dekker, New York, pp 239-265
Fessner WD, Gosse C, Jaeschke G et al. (2000) Enzymes in organic synthesis. Short enzymatic synthesis of L-fucose analogs. Eur J Org Chem 1:125-132
Fessner WD, Helaine V (2001) Biocatalytic synthesis of hydroxylated natural products using al-dolases and related enzymes. Curr Opin Biotechnol 12:574-586
Fujii M, Miura T, Kajimoto T et al. (2000) Facile synthesis of 3,4-dihydroxyprolines as an appli-cation of the L-threonine aldolase-catalyzed aldol reaction. Synlett 1046-1048
Garcia-Junceda E, Shen GJ, Sugai T et al. (1995) A new strategy for the cloning, overexpression and one step purification of three DHAP-dependent aldolases: rhamnulose-1-phosphate aldolase, fuculose 1-phosphate aldolase and tagatose 1-phosphate aldolase. Bioorg Med Chem 3:945-953
Guanti G, Banfi L, Zannetti MT (2000) Phosphonic derivatives of carbohydrates: chemoenzymatic synthesis. Tetrahed Lett 41:3181-3185
Guisan JM, Fern ández-Lafuente R, Rodríguez V et al. (1993) Enzyme stabilization by multipoint covalent attachment to activated preexisting supports. In: van den Tweel WJJ, Harder A, Buite-laar RM (eds). Stability and stabilization of enzymes, vol. 47. Elsevier, Amsterdam, pp 55-62
Henderson I, Garcia-Junceda E, Liu KK et al. (1994) Cloning, overexpression and isolation of the type II FDP aldolase from E. coli for specificity study and synthetic application. Bioorg Med Chem 2:837-843
Holmberg K (1997) Microemulsions in biotechnology In: Solans C, Kunieda H (eds). Industrial applications of microemulsions. Marcel Dekker, New York, pp 69-95
Jung SH, Jeong JH, Miller P et al. (1994) An efficient multigram-scale preparation of dihydroxyacetone phosphate. J Org Chem 59:7182-7184
Kunieda H, Rajagopalan V, Kimura E et al. (1994) Nonequilibrium structure of water in oil gel emulsions. Langmuir 10:2570-2577
Liu JQ, Dairi T, Itoh N et al. (2000a) Diversity of microbial threonine aldolases and their applications. J Mol Catal 10:107-115
Liu JQ, Odani M, Yasuoka T et al. (2000b) Gene cloning and overproduction of low-specificity D-threonine aldolase from Alcaligenes xylosoxidans and its application for production of a key intermediate for parkinsonism drug. Appl Microbiol Biotechnol 54:44-51
Machajewski TD, Wong CH (2000) The catalytic asymmetric aldol reaction. Angew Chem Int Ed Engl 39:1352-1374
Mahrwald R (2004) Modern aldol reactions, vol. 1. Enolates, organocatalysis, biocatalysis and natural product synthesis. Wiley-VCH, Weinheim, 335 pp
Phillips SA, Thornalley PJ (1993) The formation of methylglyoxal from triose phosphates. Eur J Biochem 212:101-105
Pinsach J, de Mas C, L ópez-Santín J (2006) A simple feedback control of Escherichia coli growth for recombinant aldolase production in fed-batch mode. Biochem Eng J 29:235-242
Pons R, Erra P, Solans C et al. (1993) Viscoelastic properties of gel-emulsions: their relationship with structure and equilibrium properties. J Phys Chem 97:12320-12324
Princen HM (1979) Highly concentrated emulsions. I. Cylindrical systems. J Colloid Interface Sci 71:55-66
Princen HM, Kiss AD (1986) Rheology of foams and highly concentrated emulsions. III. Static shear modulus. J Colloid Interface Sci 112:427-437
Ramsaywak PC, Labb é G, Siemann S et al. (2004) Molecular cloning, expression, purification, and characterization of fructose 1,6-bisphosphate aldolase from Mycobacterium tuberculosis -a novel Class II A tetramer. Protein Expres Purif 37:220-228
Richard JP (1993) Mechanism for the formation of methylglyoxal from triosephosphates. Biochem Soc T 21:549-553
Samland AK, Sprenger GA (2006) Microbial aldolases as C C bonding enzymes-unknown treasures and new developments. Appl Microbiol Biotechnol 71:253-264
Sauve V, Sygusch J (2001) Molecular cloning, expression, purification, and characterization of fructose-1,6-bisphosphate aldolase from Thermus aquaticus. Protein Expres Purif 21:293-302
Sch ürmann M, Sprenger GA (2001) Fructose-6-phosphate aldolase is a novel class I aldolase from Escherichia coli and is related to a novel group of bacterial transaldolases. J Biol Chem 276:11055-11061
Sch ürmann M, Sch ürmann M, Sprenger GA (2002) Fructose 6-phosphate aldolase and 1-deoxy-D-xylulose 5-phosphate synthase from Escherichia coli as tools in enzymatic synthesis of 1-deoxysugars. J Mol Catal B: Enzym 19:247-252
Shelton CM, Toone EJ (1995) Differential dye-ligand chromatography as a general purification protocol for 2-keto-3-deoxy-6-phosphogluconate aldolases. Tetrahed Asymm 6:207-211
Silvestri MG, Desantis G, Mitchell M et al. (2003) Asymmetric aldol reactions using aldolases. Top Stereochem 23:267-342
Sobolov SB, Bartoszko-Malik A, Oeschger TR et al. (1994) Crosslinked enzyme crystals of fructose diphosphate aldolase: development as a biocatalyst for synthesis. Tetrahed Lett 35:7751-7754
Solans C, Pons R, Kunieda H (1998) Gel emulsions - relationship between phase behavior and formation. In: Binks BP (ed). Modern aspects of emulsion science. The Royal Society of Chemistry, Cambridge, UK, pp 367-394
Solans C, Pinazo A, Caldero G et al. (2001) Highly concentrated emulsions as novel reaction media. Colloids Surf A 176:101-108
Steinreiber J, Sch ürmann M, Wolberg M et al. (2007) Overcoming thermodynamic and kinetic limitations of aldolase-catalyzed reactions by applying multienzymatic dynamic kinetic asymmetric transformations. Angew Chem Int Ed 46:1624-1626
Suau T, Calveras J, Clap és P et al. (2005) Immobilization of fuculose-1-phosphate aldolase from E. coli to glyoxal-agarose gels by multipoint covalent attachment. Biocatal Biotransform 23:241-250
Suau T, Alvaro G, Benaiges MD et al. (2006) Influence of secondary reactions on the synthetic efficiency of DHAP-aldolases. Biotechnol Bioeng 93:48-55
Takayama S, McGarvey GJ, Won CH (1997) Microbial aldolases and transketolases: new biocatalytic approaches to simple and complex sugars. Ann Rev Microbiol 51:285-310
Tischer W, Ihlenfeldt HG, Barzu O et al. (2001) Enzymatic synthesis of deoxyribonucleosides from deoxyribose 1-phosphate and nucleobase. Int. Patent WO014566.
Vidal L, Ferrer P, Alvaro G et al. (2005a) Influence of induction and operation mode on recombinant rhamnulose-1-phosphate aldolase production by Escherichia coli using the T5 promoter. J Biotechnol 118:75-87
Vidal L, Calveras J, Clap és P et al. (2005b) Recombinant production of serine hydroxymethyl transferase from Streptococcus thermophilus and its application in biocatalysis. Appl Microbiol Biotechnol 68:489-497
Walde P (1996) Enzymic reactions in liposomes. Curr Opin Colloid Interface Sci 1:638-644
Wasserman HH, Martin SF, Yamamoto Y (1999) Stereoselective carbon-carbon bond forming reactions. Elsevier, Oxford, UK, 417 pp
Whalen LJ, Wong CH (2006) Enzymes in organic synthesis: aldolase-mediated synthesis of iminocyclitols and novel heterocycles. Aldrichim Acta 39:63-71
Williams GJ, Woodhall T, Farnsworth LM et al. (2006) Creation of a pair of stereochemically complementary biocatalysts. J Am Chem Soc 128:16238-16247
Wymer N, Toone EJ (2000) Enzyme-catalyzed synthesis of carbohydrates. Curr Opin Chem Biol 4:110-119
Zhu W, Li ZY (2000) Synthesis of perfluoroalkylated sugars catalyzed by rabbit muscle aldolase (RAMA) J Chem Soc Perkin Trans 17:1105-1108
Alleman BC, Logan BE, Gilbertson RL (1995) Degradation of pentachlorophenol by fixed films of white-rot fungi in rotating tube bioreactors. Water Res 29(1):61-67
Archibald F, Paice MG, Jurasek L (1990) Decolorization of kraft bleachery effluent chromophores by Coriolus (Trametes) versicolor. Enzyme Microb Technol 12:846-853
Basheer S, Kut OM, Prenosil JE et al. (1993) Development of an enzyme membrane reactor for treatment of cyanide-containing wastewaters from the food industry. Biotechnol Bioeng 41(4):465-473
Bhunia A, Durani S, Wangikar PP (2001) Horseradish peroxidase catalyzed degradation of indus-trially important dyes. Biotechnol Bioeng 72:562-567
Bogan BW, Lamar RT (1995) One-electron oxidation in the degradation of creosote polycyclic aromatic hydrocarbons by Phanerochaete chrysosporium. Appl Environ Microbiol 61(7):2631-2635
Bogan BW, Lamar RT, Hammel KE (1996) Fluorene oxidation in vivo by Phanerochaete chrysosporium and in vitro during manganese peroxidase-dependent lipid peroxidation. Appl Environ Microbiol 62:1788-1792
Bumpus JA (1989) Biodegradation of polycyclic aromatic hidrocarbons by Phanerochaete chrysosporium. Appl Environ Microbiol 55:154-158
Chen PJ, Rosenfeldt EJ, Kullman SW et al. (2007) Biological assessments of a mixture of en-docrine disruptors at environmentally relevant concentrations in water following UV/H2 O2 ox-idation. Sci Total Environ 376(1-3):18-26
Cripps C, Bumpus JA, Aust SD (1990) Biodegradation of azo and heterocyclic dyes by Phane-rochaete chrysosporium. Appl Environ Microbiol 56(4):1114-1118
Dec J, Bollag JM (1995) Effect of various factors on dehalogenation of chlorinated phenols and anilines during oxidative coupling. Environ Sci Technol 29(3):657-663
D éziel E, Comeau Y, Villemur R (1999) Two-liquid-phase bioreactors for enhanced degradation of hydrophobic/toxic compounds. Biodegradation 10:219-233
Efroymson RA, Alexander M (1995) Reduced mineralization of low concentrations of phenan-threne because of sequestering in nonaqueous-phase liquids. Environ Sci Technol 29:515-521
Eibes G, Lu Chau T, Feijoo G et al. (2005) Complete degradation of anthracene by manganese peroxidase in organic solvent mixtures. Enzyme Microb Technol 37(4):365-372
Eibes G, Cajthaml T, Moreira MT et al. (2006) Enzymatic degradation of anthracene, diben-zothiophene and pyrene by manganese peroxidase in media containing acetone. Chemosphere 64 (3):408-414
Eibes G, Moreira MT, Feijoo G et al. (2007) Operation of a two-phase partitioning bioreactor for the oxidation of anthracene by the enzyme manganese peroxidase. Chemosphere 66:1744-1751
Field JA, Vledder RH, van Zelst JG et al. (1996). The tolerance of lignin peroxidase and manganese-dependent peroxidase to miscible solvents and the in vitro oxidation of anthracene in solvent:water mixtures. Enzyme Microb Technol 18:300-308
Fujita M, Ike M, Kusunoki K et al. (2002) Removal of color and estrogenic substances by fungal reactor equipped with ultrafiltration unit. Water Sci Technol 2(5-6):353-358
Grabski AC, Grimek HJ, Burges RR (1998) Immobilization of manganese peroxidase from Lentin-ula edodes and its biocatalytic generation of MnIII-chelate as a chemical oxidant of chlorophe-nols. Biotechnol Bioeng 60:204-215
Guis án JM, Bastida A, Blanco RM et al. (1997) Immobilization of enzymes acting on macromolec-ular substrates. Reduction of steric problems. In: Bickerstaff GF (ed). Methods in biotechnology. Immobilization of enzymes and cells. Humana Press, Totowa, USA, pp 261-275
G ünther T, Sack U, Hofrichter M et al. (1998) Oxidation of PAH and PAH-derivatives by fungal and plant oxidoreductases. J Basic Microbiol 38(2):113-122
Hammel KE, Kalyanaraman B, Kirk TK (1986) Oxidation of polycyclic aromatic hydro-carbons and dibenzo[p]-dioxins by Phanerochaete chrysosporium ligninase. J Biol Chem 261 (36):16948-16952
Heinfling A, Martínez MJ, Martínez AT et al. (1998) Transformation of industrial dyes by man-ganese peroxidases from Bjerkandera adusta and Pleurotus eryngii in a manganese-independent reaction. Appl Environ Microbiol 64:2788-2793
Hofrichter M, Ziegenhagen D, Vares T et al. (1998) Oxidative decomposition of malonic acid as basis for the action of manganese peroxidase in the absence of hydrogen peroxide. FEBS Lett 434:362-366
Hublik G, Schinner F (2000) Characterization and immobilization of the laccase from Pleurotus ostreatus and its use for the continuous elimination of phenolic pollutants. Enzyme Microb Technol 27:330-336
Isono Y, Nakajima M (2000) Membrane phase separation of aqueous/alcohol biphase mixture and its application for enzyme bioreactor. Prog Biotechnol 16:63-68
Jaspers CJ, Jimenez G, Penninckx MJ (1994) Evidence for a role of manganese peroxidase in the decolorization of Kraft pulp bleach plant effluent by Phanerochaete chrysosporium: effects of initial culture conditions on enzyme production. J Biotechnol 37(3):229-234
Johannes C, Majcherczyk A, Huttermann A (1996) Degradation of anthracene by laccase of Tram-etes versicolor in the presence of different mediator compounds. Appl Microbiol Biotechnol 46 (3):313-317
Katchalski-Katzir E, Kraemer DM (2000) Eupergit○R C, a carrier for immobilization of enzymes of industrial potential. J Mol Catal B Enzym 10:157-176
Kelsey LJ, Pillarella MR, Zydney AL (1990) Theoretical analysis of convective flow profiles in a hollow-fiber membrane bioreactor. Chem Eng Sci 45:3211-3220
Klibanov AM (2001) Improving enzymes by using them in organic solvents. Nature 409(11):241-246
K öhler A, Sch üttoff M, Bryniok D et al. (1994) Enhanced biodegradation of phenanthrene in a biphasic culture system. Biodegradation 5:93-103
Kotterman MJJ, Rietberg HJ, Hage A et al. (1998) Polycyclic aromatic hydrocarbon oxidation by the white-rot fungus Bjerkandera sp. strain BOS55 in the presence of nonionic surfactants. Biotechnol Bioeng 57(2):220-227
Krastanov A (2000) Removal of phenols from mixtures by co-immobilized laccase/tyrosinase and Polycar adsorption. J Ind Microbiol Biotechnol 24:383-388
Kuan IC, Tien M (1993) Stimulation of manganese peroxidase activity: a possible role for oxalate in lignin biodegradation. Proc Natl Acad Sci USA 90:1242-1246
Lante A, Crapisi A, Krastanov A et al. (2000) Biodegradation of phenols by laccase immobilised in a membrane reactor. Proc Biochem 36(1-2):51-58
Lee C, Yoon J, von Gunten U (2007) Oxidative degradation of N -nitrosodimethylamine by con-ventional ozonation and the advanced oxidation process ozone/hydrogen peroxide. Water Res 41 (3):581-590
L ópez C, Mielgo I, Moreira MT et al. (2002) Enzymatic membrane reactors for biodegradation of recalcitrant compounds. Application to dye decolourisation. J Biotechnol 99(3):249-257
L ópez C, Moreira MT, Feijoo G et al. (2004) Dye decolorization by manganese peroxidase in an enzymatic membrane bioreactor. Biotechnol Prog 20(1):74-81
L ópez C, Moreira MT, Feijoo G et al. (2007) Dynamic modeling of an enzymatic membrane reactor for the treatment of xenobiotic compounds. Biotechnol Bioeng 97(5):1128-1137
MacLeod CT, Daugulis AJ (2003) Biodegradation of polycyclic aromatic hydrocarbons in a two-phase partitioning bioreactor in the presence of a bioavailable solvent. Appl Microbiol Biotech-nol 62:291-296
Majcherczyk A, Johannes C, Huttermann A (1998) Oxidation of polycyclic aromatic hydrocarbons (PAH) by laccase of Trametes versicolor. Enzyme Microb Technol 22(5):335-341
Marcoux J, D éziel E, Villemur R et al. (2000) Optimization of high-molecular-weight poly-cyclic aromatic hydrocarbons’ degradation in a two-liquid-phase bioreactor. J Appl Microbiol 88 (4):655-662
M éndez-Paz D, Omil F, Lema JM (2005) Anaerobic treatment of azo dye Acid Orange 7 under batch conditions. Enzyme Microb Technol 36:264-272
Mielgo I, Moreira MT, Feijoo et al. (2002) Biodegradation of a polymeric dye in a pulsed bed bioreactor by immobilised Phanerochaete chrysosporium. Water Res 36:1896-1901
Mielgo I, L ópez C, Moreira MT et al. (2003) Oxidative degradation of azo dyes by manganese peroxidase under optimized conditions. Biotechnol Prog 19(2):325-331
Moen MA, Hammel KE (1994) Lipid peroxidation by the manganese peroxidase of Phanerochaete chrysosporium is the basis for phenanthrene oxidation by the intact fungus. Appl Environ Mi-crobiol 60:1956-1961
Ollikka P, Alhonm äki K, Lepp änen VM et al. (1993) Decolorization of azo, triphenyl methane, het-erocyclic, and polymeric dyes by lignin peroxidase isoenzymes from Phanerochaete chrysospo-rium. Appl Environ Microbiol 59:4010-4016
Palma C, Moreira MT, Feijoo G et al. (1997) Enhanced catalytic properties of MnP by exogenous addition of manganese and hydrogen peroxide. Biotechnol Lett 19(3):263-267
Pasta P, Carrea G, Monzani E et al. (1999). Chloroperoxidase-catalyzed enantioselective oxida-tion of methyl phenyl sulfide with dihydroxyfumaric acid/oxygen or ascorbic acid/oxygen as oxidants. Biotechnol Bioeng 62(4):489-493
Pickard MA, Roman R, Tinoco R et al. (1999) Polycyclic aromatic hydrocarbon metabolism by white rot fungi and oxidation by Coriolopsis gallica UAMH 8260 laccase. Appl Environ Mi-crobiol 65(9):3805-3809
Prazeres DMF, Cabral JMS (1994) Enzymatic membrane bioreactors and their applications. En-zyme Microb Technol 16:738-750
Rodakiewicz-Nowak J, Jarosz-Wilkolazka A (2007) Catalytic activity of Cerrena unicolor laccase in aqueous solutions of water-miscible organic solvents - experimental and numerical descrip-tion. J Mol Catal B Enzym 44(2):53-59
Roper JC, Sarkar JM, Dec J et al. (1995) Enhanced enzymatic removal of chlorophenols in the presence of co-substrates. Water Res 29(12):2720-2724
Ross AC, Bell G, Halling PJ (2000) Organic solvent functional group effect on enzyme inactivation by the interfacial mechanism. J Mol Catal B Enzym 8:183-192
Sasaki T, Kajino T, Li B et al. (2001) New pulp biobleaching system involving manganese per-oxidase immobilized in a silica support with controlled pore sizes. Appl Environ Microbiol 67 (5):2208-2212
Scheibner K, Hofrichter M (1998) Conversion of aminonitrotoluenes by fungal manganese perox-idase. J Basic Microbiol 38(1):51-59
Steffen KT, Hatakka A, Hofrichter M (2003) Degradation of benzo[a]pyrene by the litter-decomposing basidiomycete Stropharia coronilla: role of manganese peroxidase. Appl Environ Microbiol 69(7):3957-3964
Su árez S, Dodd MC, Omil F et al. (2007) Kinetics of triclosan oxidation by aqueous ozone and consequent loss of antibacterial activity: relevance to municipal wastewater ozonation. Water Res 41(12):2481
Timofeevski SL, Reading NS, Aust SD (1998) Mechanisms for protection against inactivation of manganese peroxidase by hydrogen peroxide. Arch Biochem Biophys 356(2):287-295
Valli K, Wariishi H, Gold MH (1992) Degradation of 2,7-dichlorodibenzo-p-dioxin by the lignin-degrading basidiomycete Phanerochaete chrysosporium. J Bacteriol 174(7):2131-2137
van Aken B, Agathos SN (2002). Implication of manganese (III), oxalate, and oxygen in the degra-dation of nitroaromatic compounds by manganese peroxidase (MnP). Appl Microbiol Biotech-nol 58(3):345-351
van Aken B, Godefroid LM, Peres CM et al. (1999) Mineralization of C-14-U-ring labeled 4-hydroxylamino-2,6dinitrotoluene by manganese-dependent peroxidase of the whiterot basid-iomycete Phlebia radiata. J Biotechnol 68(2-3):159-169
Welty JR, Wicks CE, Wilson RE (1984) Fundamentals of momentum, heat, and mass transfer. John Wiley and Sons, New York, 803 pp
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Barberis, S. et al. (2008). Study Cases of Enzymatic Processes. In: Illanes, A. (eds) Enzyme Biocatalysis. Springer, Dordrecht. https://doi.org/10.1007/978-1-4020-8361-7_6
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