Abstract
This paper presents an updated critical review about several attempts to contribute methionine (Met) to the world market with an emphasis on fermentation processes, especially from natural biological sources. Analytical methods for the determination of methionine are reviewed as well as applications in feed, food, pharmacy, and medicine. Fermentation studies published within the last five decades are elucidated critically, mainly with respect to the sulfur balance, substrate yield, and the analytical validity. From all the published fermentation data, it can be concluded that up to now no more than 5 g/L methionine are achievable without using genetically modified organisms (GMOs). The highest l-methionine concentration from natural sources reached so far amounts to 35 g/L and is published as a patent using a GMO of Escherichia coli. The review closes with a comprehensive overview of the role and activities of global methionine manufacturers. Some current market data is also presented.
Similar content being viewed by others
References
Ables GP, Brown-Borg HM, Buffenstein R, Church CD, Elshorbagy AK, Gladyshev VN, Huang TH, Miller RA, Mitchell JR, Richie JP, Rogina B, Stipanuk MH, Orentreich DS, Orentreich N (2014) The First International Mini-Symposium on Methionine Restriction and Lifespan. Front Genet 5:122. doi:10.3389/fgene.2014.00122
Acharjee S, Sarmah BK (2013) Biotechnologically generating ‘super chickpea’ for food and nutritional security. Plant Sci 207:108–116
Adrio JL, Demain AL (2006) Genetic improvement of processes yielding microbial products. FEMS Microbiol Rev 30(2):187–214
Agrafiotou P, Sotiropoulos S, Pappa-Louisi A (2009) Direct RP-HPLC determination of underivatized amino acids with online dual UV absorbance, fluorescence, and multiple electrochemical detection. J Sep Sci 32(7):949–954. doi:10.1002/jssc.200800636
Ajinomoto (2014) l-Methionine—product details. Ajinomoto. www.ajiaminoscience.com/products/manufactured_products/l-amino_acids/L-Methionine.aspx. Accessed 14 Jul 2014
Alfoldi L (1958) La production induite de magacine en milieu synthethique. Annales de l Institut Pasteur 94(4):474–484
Ali NM, Shakoori FR, Shakoore AR (2011) Improvement in methionine production by local bacterial isolates. Pak J Zool 43(3):611–614
Altenbach SB, Pearson KW, Meeker G, Staraci LC, Sun SM (1989) Enhancement of the methionine content of seed proteins by the expression of a chimeric gene encoding a methionine-rich protein in transgenic plants. Plant Mol Biol 13(5):513–522
Altenbach SB, Kuo CC, Staraci LC, Pearson KW, Wainwright C, Georgescu A, Townsend J (1992) Accumulation of a Brazil nut albumin in seeds of transgenic canola results in enhanced levels of seed protein methionine. Plant Mol Biol 18(2):235–245
Anakwenze VM, Ezemba CC, Ekwealor IA (2014) Optimization of fermentation conditions of Bacillus thuringiensis EC1 for enhanced methionine production. Adv Microbiol 4(7):344–352. doi:10.4236/aim.2014.47041
Anike N, Okafor N (2008) Secretion of methionine by microorganisms associated with Cassava fermentation. African Journal of Good Agriculture, Nutrition and Development 8(1)
Anonymus (2002) Adisseo takes off. Animal Pharm 482:14 www.agra-net.net/agra/animal-pharm/adisseo-takes-off--1.htm Accessed 14 Jul 2014
Anupama, Ravindra P (2000) Value-added food: single cell protein. Biotechnol Adv 18(6):459–479. doi:10.1016/S0734-9750(00)00045-8
Arkema (2011) Press release: CJ CheilJedang and Arkema announce a project to build the world’s first bio-methionine plant and a thiochemicals platform in Asia. www.arkema.com/export/sites/global/.content/medias/downloads/investorrelations/en/press-release/2011/cj-and-arkema-press-release-va.pdf. Accessed 14 Jul 2014
Banik AK, Majumdar SK (1974) Studies on methionine fermentation.1. Selection of mutants of Micrococcus glutamicus and optimum conditions for methionine production. Indian J Exp Biol 12(4):363–365
Banik AK, Majumdar SK (1975) Effects of minerals on mroduction of methionine by Micrococcus glutamicus. Indian J Exp Biol 13(5):510–512
Barger G, Coyne FP (1928) The amino-acid methionine; constitution and synthesis. Biochem J 22(6):1417–1425
Becker J, Wittmann C (2012) Systems and synthetic metabolic engineering for amino acid production—the heartbeat of industrial strain development. Curr Opin Biotechnol 23(5):718–726. doi:10.1016/j.copbio.2011.12.025
Bestel-Corre G, Boisart C, Figge R (2012) Patent to Metabolic Explorer: Recombinant microorganism for the fermentative production of methionine. WO2012/090021(A1)
Bluestar (2014) Press release: Bluestar Adisseo’s methionine project goes into production. www.china-bluestar.com/lanxingen/xwymt/hhxw/webinfo/2014/02/1393464230941395.htm
Bolten CJ, Schroder H, Dickschat J, Wittmann C (2010) Towards methionine overproduction in Corynebacterium glutamicum—methanethiol and dimethyldisulfide as reduced sulfur sources. J Microbiol Biotechnol 20(8):1196–1203. doi:10.4014/jmb.1002.02018
Boy M, Klein D, Schroeder H (2005) Patent to BASF AG: Method for the production of methionine. WO2005059155(A2)
Brazeau B, Chang J-S, Cho KM, Cho YW, Desouza M, Jessen HJ, Kim S-Y, Niu W, Sanchez-Reira FA, Shin Y-U, Um H (2013) Patent to CJ CheilJedang Corporation, Seoul (KR): Compositions and methods of producing methionine. US2013/0260424(A1)
Brigidi P, Matteuzzi D, Fava F (1988) Use of protoplast fusion to introduce methionine overproduction into Saccharomyces cerevisiae. Appl Microbiol Biotechnol 28(3):268–271
Cavazza A, Corradini C, Lauria A, Nicoletti I, Stancanelli R (2000) Rapid analysis of essential and branched-chain amino acids in nutraceutical products by micellar electrokinetic capillary chromatography. J Agric Food Chem 48(8):3324–3329. doi:10.1021/jf991368m
CCM (2014) Capacity of methionine in china, 2013. CCM Data & Business Intelligence. Guangzhou, China www.cnchemicals.com/Product/Release/5851/capacity-of-methionine-in-china-2013. Accessed 14 Jul 2014
Chalova VI, Froelich CA Jr, Ricke SC (2010) Potential for development of an Escherichia coli-based biosensor for assessing bioavailable methionine: a review. Sensors (Basel, Switzerland) 10(4):3562–3584. doi:10.3390/s100403562
Chattopadhyay MK, Ghosh AK, Sengupta S, Sengupta D, Sengupta S (1995) Threonine analogue resistant mutants of Escherichia coli K-12. Biotechnol Lett 17(6):567–570
Chinard FP (1952) Photometric estimation of proline and ornithine. J Biol Chem 199(1):91–95
CIA (1999) The Soviet hydrocarbon-based single cell protein program, April 1977 (sanitized release). In: CIA (ed) National security information. USA. http://www.ascension-publishing.com/BIZ/CIA-microalgae-Soviet.pdf. Accessed 14 Jul 2014
Cobb Z, Shaw PN, Lloyd LL, Wrench N, Barrett DA (2001) Evaporative light-scattering detection coupled to microcolumn liquid chromatography for the analysis of underivatized amino acids: sensitivity, linearity of response and comparisons with UV absorbance detection. J Microcolumn Sep 13(4):169–175
Cohen M (2007) “Nippon Soda Co. Ltd.” International directory of company histories encyclopedia. vol 85. www.encyclopedia.com/doc/1G2-2690100070.html. Accessed 14 Jul 2014
Coppex L, Walz R (2000) Derivatives for HPLC analysis. Diploma Thesis, University of Genf http://de.scribd.com/doc/189706760/Derivatives-for-HPLC-Analysis. Accessed 14 Jul 2014
Danneel HJ (2005) Final report of an R&D project: development of a process for recovering l-methionine from press cake of Brazil nut: Projektlaufzeit: 01.09.2003-31.05.2005 (German). FH Lippe u. Höxter, FB Life Science Technologies; Technische Informationsbibliothek u. Universitätsbibliothek, Lemgo
Dassler T, Leinfelder W, Wich G (2014) Patent to Wacker Chemie AG: Method of fermentative production of l-cysteine and derivatives of said amino acid. WO2014/040955(A1)
De Luca A, Sanna F, Sallese M, Ruggiero C, Grossi M, Sacchetta P, Rossi C, De Laurenzi V, Di Ilio C, Favaloro B (2010) Methionine sulfoxide reductase a down-regulation in human breast cancer cells results in a more aggressive phenotype. Proc Natl Acad Sci U S A 107(43):18628–18633
Dever JT, Elfarra AA (2010) The biochemical and toxicological significance of Hypermethionemia: new insights and clinical relevance. Expert Opin Drug Metabol Toxicol 6(11):1333–1346. doi:10.1517/17425255.2010.522177
Difco (1953) Methionine assay medium (B423). Difco Manual of Dehydrated Media and Reagents for Microbiological and Clinical Laboratory Procedures. 9 edn. Difco Laboratories Inc., Detroit, p 232. https://archive.org/stream/difcomanualofdeh09dige#page/232. Accessed 14 July 2014
Dike KS, Ekwealor IA (2012) Studies on process and physical parameters for the production of l-methionine from newly isolated Bacillus cereus strains. Asian J Biol Sci 5(2):96–104. doi:10.3923/ajbs.2012.96.104
Dischert W, Figge R (2013a) Patent to MetabolicExplorer: A microorganism for methionine production with enhanced glucose import. WO2013/001055(A1)
Dischert W, Figge R (2013b) Patent to MetabolicExplorer: Recombinant microorganism for the fermentative production of methionine. WO2013/190343(A1)
Dischert W, Vasseur P, Boisart C, Figge R (2013) Patent to MetabolicExplorer: Increasing NADH availability for methionine production. US2013/0183727
Dolowy M, Pyka A (2014) Application of TLC, HPLC and GC methods to the study of amino acid and peptide enantiomers: a review. Biomed Chromatogr: BMC 28(1):84–101. doi:10.1002/bmc.3016
Drazic A, Winter J (2014) The physiological role of reversible methionine oxidation. Biochim Biophys Acta 1844(8):1367–1382. doi:10.1016/j.bbapap.2014.01.001
DSM (2014) Press release: DSM opens new animal nutrition center to support Chinese livestock production industry. www.dsm.com/content/dam/dsm/cworld/en_US/documents/2014-05-19-dsm-opens-new-animal-nutrition-center-to-support-chinese-livestock-production-industry.pdf?fileaction=openFile. Accessed 14 July 2014
Dulaney EL, Jones CA, Dulaney D (1964) Amino acid accumulation, principally alanine, by auxotrophs of Ustilago maydis. Dev Ind Microbiol 5:242–249
Dupont (2013) Product specification sheet: Betafin natural betaine at its best for excellent animal productivity. Danisco Animal Nutrition. Marlborough, Wiltshire, UK. http://animalnutrition.dupont.com/fileadmin/user_upload/live/animal_nutrition/documents/open/DuPont_Betafin.pdf. Accessed 14 July 2014
EC (1998) Commision Directive 98/64/Ec-Annex part A: determination of amino acids. Official Journal of the European Communities L257(14). http://eur-lex.europa.eu/legal-content/EN/TXT/PDF/?uri=CELEX:31998L0067&from=EN. Accessed 14 Jul 2014
EC (2008) Commision Regulation (EC) No 889/2008 of 5 September 2008: laying down detailed rules for the implementation of Council Regulation (EC) No 834/2007 on organic production and labelling of organic products with regard to organic production, Labelling and Control Vol 889. http://eur-lex.europa.eu/LexUriServ/LexUriServ.do?uri=OJ:L:2008:250:0001:0084:EN:PDF. Accessed 14 Jul 2014
EC (2014a) Proposal for a regulation of the European Parliament and of the Council. http://ec.europa.eu/agriculture/organic/documents/eu-policy/policy-development/report-and-annexes/proposal_en.pdf. Accessed 14 Jul 2014
EC (2014b) European Union Register of Feed Additives pursuant to Regulation (EC) No 1831/2003-Appendixes 3e & 4(I). Annex I: list of additives vol 1831/2003, 193 edn. http://ec.europa.eu/food/food/animalnutrition/feedadditives/docs/comm_register_feed_additives_1831-03.pdf. Accessed 7 Oct 2014
EFSA (2013) Scientific opinion on the safety and efficacy of l-methionine produced by Escherichia coli (KCCM 11252P) and Escherichia coli (KCCM 11340P) for all animal species. EFSA Journal 11(10):3428
Eggeling L, Sahm H (2009) Amino acid production. In: Schaechter M (ed) Encyclopedia of microbiology (third edition). Academic Press, Oxford, pp 150–158. www.sciencedirect.com/science/article/pii/B9780123739445001292. Accessed 14 Jul 2014
Eggeling L, Sahm H (2011) Amino acid production. In: Moo-Young M (ed) Comprehensive biotechnology (second edition). Academic Press, Burlington, pp 531–539. www.sciencedirect.com/science/article/pii/B9780080885049005407. Accessed 14 Jul 2014
Evonik (2014a) Press release: Evonik invests in innovative methionine source for shrimp in growth market aquaculture. http://corporate.evonik.com/en/investor-relations/news-reports/investor-relations-news/pages/news-details.aspx?newsid=42301. Accessed 14 Jul 2014
Evonik (2014b) Universities succeed at Evonik idea competition. Elements - Degussa Science Newsletter 46(1):21. http://corporate.evonik.de/en/media/publications/elements/Pages/default.aspx. Accessed 14 Jul 2014
Fanatico A (2010) Organic poultry production: providing adequate methionine. ATTRA-National Sustainable Agriculture Information Service (IP363) www.attra.ncat.org/attra-pub/PDF/methionine.pdf. Accessed 14 Jul 2014
FAO (2004) Protein sources for the animal feed industry. In: FAO (ed) Expert consultation and workshop, Bangkok, 29 April–May 2002 2002. FAO, Rome. http://www.fao.org/docrep/007/y5019e/y5019e00.htm#Contents. Accessed 14 Jul 2014
FAO (2014) Market reports on fishoil and fishmeal. FAO-Fisheries and Aquaculture Department, Rome. www.globefish.org/fish-oil-and-fishmeal-market-reports.html. Accessed 14 Jul 2014
FAO/WUR (2013) Edible insects: future prospects for food and feed security. FAO, Rome. www.fao.org/docrep/018/i3253e/i3253e.pdf. Accessed 14 Jul 2014
Farahnak F, Seki T, Ryu DDY, Ogrydziak D (1986) Construction of lactose-assimilating and high-ethanol-producing yeasts by protoplast fusion. Appl Environ Microbiol 51(2):362–367
FeedInfo (2014) Methionine: supply/demand overview 2014. FeedInfo news service. www.feedinfo.com. Accessed 14 Jul 2014
Figge R (2007) Methionine biosynthesis in Escherichia coli and Corynebacterium glutamicum. In: Wendisch VF (ed) Amino acid biosynthesis - pathways, regulation and metabolic engineering. Microbiology Monographs, vol 5. Springer, Berlin, pp 163–193
Figge R, Lux F, Raynaud C, Chateau M, Soucaille P (2007) Patent to MetabolicExplorer: Process for the preparation of methionine and its precursors homoserine or succinylhomoserine employing a microorganism with enhanced sulfate permease expression. WO2007/077041(A1)
Figge R, Soucaille P, Barbier G, Bestel-Corre G, Boisart C, Chateau M (2009) Patent to MetabolicExplorer: Increasing methionine yield. WO2009/043372(A1)
Fink K, Fink RM, Cline RE (1963) Paper chromatography of several classes of compounds—correlated Rf values in a variety of solvent systems. Anal Chem 35(3):389
Fleitmann T (1848) Bestimmungen des Verhältnisses, in welchem der Schwefel in seinen zwei verschiedenen Formen in den schwefel- und stickstoffhaltigen organischen Verbindungen enthalten ist. Justus Liebigs Annalen der Chemie 66(3):380–381. doi:10.1002/jlac.18480660313
Fremy G, Barre P, Kim S-Y, Son SK, Lee SM (2013) Patent to Arkema France-CJ CheilJedang China: Preparation process of l-methionine. WO2013/029690(A1)
Froelich CA, Zabala Diaz IB, Ricke SC (2002) Construction and growth kinetics of a bioluminescent methionine auxotroph Escherichia coli strain for potential use in a methionine bioassay. J Rapid Methods Autom Microbiol 10(2):69–82
Froelich CA, Ricke SC (2005) Rapid bacterial-based bioassays for quantifying methionine bioavailability in animal feeds: a review. J Rapid Methods Autom Microbiol 13(1):1–10. doi:10.1111/j.1745-4581.2005.00001.x
Früh B (2014) Eiweissversorgung-Welche Möglichkeiten gibt es? (German-Deutsch). Ökologie und Landbau 170(2):15–17
Gabbita SP, Aksenov MY, Lovell MA, Markesbery WR (1999) Decrease in peptide methionine sulfoxide reductase in Alzheimer’s disease brain. J Neurochem 73(4):1660–1666
Giri KV, Rao NAN (1952) A technique for the identification of amino-acids separated by circular paper chromatography. Nature 169(4309):923–924. doi:10.1038/169923a0
Giri KV, Krishnamurthy K, Venkitasubramanian TA (1952) Simple paper chromatographic technique for amino-acid analysis of blood. Lancet 263:562–563
Goldberg I (1985) Single cell protein. Springer Berlin Heidelberg. doi:10.1007/978-3-642-46540-6
Gomes J, Kumar D (2005) Production of l-methionine by submerged fermentation: a review. Enzym Microb Technol 37(1):3–18
Goodson J, Thomson J, Helmbrecht A (2012) Feeding value of l-methionine versus dl-methionine. Animal AG Resource Center, Evonik Whitepaper Aug 2012. www.wattagnet.com/158381.html. Accessed 14 Jul 2014
Greenstein JP, Wintz M (1961) Methionine. In: Chemistry of the amino acid, vol. 3. Wiley, New York, pp 2125–2155
Hartwich T (2008) Untersuchungen zur biotechnischen Methionin-Produktion in Corynebacterium glutamicum ATCC 13032-Entwicklung einer Screening-Strategie. Dissertation. Technical University of Braunschweig, Germany
Hermann T (2003) Industrial production of amino acids by coryneform bacteria. J Biotechnol 104(1–3):155–172. doi:10.1016/S0168-1656(03)00149-4
Himmel ME, Ding S-Y, Johnson DK, Adney WS, Nimlos MR, Brady JW, Foust TD (2007) Biomass recalcitrance: engineering plants and enzymes for biofuels production. Science 315(5813):804–807. doi:10.1126/science.1137016
Höfler A, Alt H-C, Klasen C-J, Friedrich H, Hertz U, Mörl L, Schütte R (2012) Patent to Degussa: Verfahren zur Herstellung eines Tierfutter-Zusatzes auf Fermentationsbrühe-Basis. DE19621930(C1)
Hong SW, Kwang IS, Lee SM, Lee YJ, Jung JY, Eyal A (2012) Patent to CJ CheilJedang Corporation: Methods for production of l-methionine and related products. WO2012/091479(A9)
Hummel W, Geueke B, Osswald S, Weckbecker C, Huthmacher K (2005) Patent to Degussa: Methods of the preparation of l-amino acids from d-amino acids. US7217544(B2)
Husek P (2000) Patent to Phenomenex: Method of preparing sample for amino acid analysis and kit for analyzing the same. EP1033576(A2)
Husek P, Simek P (2001) Advances in amino acid analysis. LC GC N Am 19(9):986
Husek P, Sweeley CC (1991) Gas-chromatographic separation of protein amino-acids in 4 minutes. HRC-J High Resolut Chromatogr 14(11):751–753
Ikeda M, Takeno S (2013) Amino acid production by Corynebacterium glutamicum. In: Yukawa H, Inui M (eds) Corynebacterium glutamicum. Microbiology Monographs, vol 23. Springer, Berlin, pp 107–147
Jankowski J, Kubinska M, Zdunczyk Z (2014) Nutritional and immunomodulatory function of methionine in poultry diets—a review. Ann Anim Sci 14(1):17–31. doi:10.2478/aoas-2013-0081
Jilin (2013) Annual output of 100,000 tons of methionine. Project of Jilin City. Jilin, China. http://english.jl.gov.cn/Investment/Opportunities/Industry/syhg/201303/t20130319_1430986.html. Accessed 14 Jul 2014
Joson ER, Klug HL (1956) A microchemical modification of the McCarthy and Sulivan method for the determination of methionine. Proc S D Acad Sci 35:48–60
Kalinowski J, Bathe B, Bartels D, Bischoff N, Bott M, Burkovski A, Dusch N, Eggeling L, Eikmanns BJ, Gaigalat L, Goesmann A, Hartmann M, Huthmacher K, Kramer R, Linke B, McHardy AC, Meyer F, Mockel B, Pfefferle W, Puhler A, Rey DA, Ruckert C, Rupp O, Sahm H, Wendisch VF, Wiegrabe I, Tauch A (2003) The complete Corynebacterium glutamicum ATCC 13032 genome sequence and its impact on the production of l-aspartate-derived amino acids and vitamins. J Biotechnol 104(1–3):5–25
Kawerau E, Wieland T (1951) Conservation of amino-acid chromatograms. Nature 168(4263):77–78
Kiene RP, Linn LJ, Gonzalez J, Moran MA, Bruton JA (1999) Dimethylsulfoniopropionate and methanethiol are important precursors of methionine and protein-sulfur in marine bacterioplankton. Appl Environ Microbiol 65(10):4549–4558
Kim S-Y, Cho KM, Shin Y-U, Um H-W, Choi K-O, Chang J-S, Cho Y-W, Park Y-H (2008) Patent to CJ CheilJedang: Microorganism producing l-methionine precursor and method of producing l-methionine and organic acid from l-methionine precursor. WO2008/0134329(A9)
Kitamoto HK, Nakahara T (1994) Isolation of an l-methionine-enriched mutant of Kluyveromyces lactis grown on whey permeate. Process Biochem 29(2):127–131. doi:10.1016/0032-9592(94)80005-7
Komatsu K, Yamada T, Kodaira R (1974) Isolation and characteristics of pool methionine-rich mutants of a Candida sp. J Ferment Technol 52(2):93–99
Kröger B, Zelder O, Klopprogge C, Schroder H, Häfner S (2003) Patent to BASF: Methods for producing sulphurous fine chemicals. WO2002/087386(A2)
Krömer JO, Fritz M, Heinzle E, Wittmann C (2005) In vivo quantification of intracellular amino acids and intermediates of the methionine pathway in Corynebacterium glutamicum. Anal Biochem 340(1):171–173
Krömer JO, Wittmann C, Schröder H, Heinzle E (2006) Metabolic pathway analysis for rational design of l-methionine production by Escherichia coli and Corynebacterium glutamicum. Metab Eng 8(4):353–369. doi:10.1016/j.ymben.2006.02.001
Kumar D, Gomes J (2005) Methionine production by fermentation. Biotechnol Adv 23(1):41–61
Kumar D, Garg S, Bisaria VS, Sreekrishnan TR, Gomes J (2003) Production of methionine by a multi-analogue resistant mutant of Corynebacterium lilium. Process Biochem 38(8):1165–1171
Lawrence DA, Smith DA, Rowbury RJ (1968) Regulation of methionine synthesis in Salmonella typhimurium—mutants resistant to inhibition by analogues of methionine. Genetics 58(4):473
Lee HS, Hwang BJ (2003) Methionine biosynthesis and its regulation in Corynebacterium glutamicum: parallel pathways of transsulfuration and direct sulfhydrylation. Appl Microbiol Biotechnol 62(5–6):459–467
Lee TTT, Wang MMC, Hou RCW, Chen L-J, Su R-C, Wang C-S, Tzen JTC (2003) Enhanced methionine and cysteine levels in transgenic rice seeds by the accumulation of sesame 2 s albumin. Biosci Biotechnol Biochem 67(8):1699–1705. doi:10.1271/bbb.67.1699
Lee BC, Kaya A, Ma S, Kim G, Gerashchenko MV, Yim SH, Hu Z, Harshman LG, Gladyshev VN (2014) Methionine restriction extends lifespan of Drosophila melanogaster under conditions of low amino-acid status. Nat Commun 5. doi:10.1038/ncomms4592
Legmann R, Margalith P (1986) Ethanol formation by hybrid yeasts. Appl Microbiol Biotechnol 23(3–4):198–202
Lievense JC (1993) Patent to Genencor: Biosynthesis of methionine using a reduced source of sulfur. WO1993/17112
Lüssling T, Müller K-P, Schreyer G, Theissen F (1981) Patent to Deutsche Gold- und Silber-Scheideanstalt formerly Roessler (Degussa): Process for the recovery of methionine and potassium bicarbonate. US4303621(A)
Maier T, Winterhalter C, Pfeiffer K (2004) Patent to Wacker Chemie AG: Method of fermentative production of l-methionine. EP1445310(B1)
Mampel J, Schröder H, Haefner S, Sauer U (2005) Single-gene knockout of a novel regulatory element confers ethionine resistance and elevates methionine production in Corynebacterium glutamicum. Appl Microbiol Biotechnol 68(2):228–236
Martinez-Cuesta MD, Pelaez C, Requena T (2013) Methionine metabolism: major pathways and enzymes involved and strategies for control and diversification of volatile sulfur compounds in cheese. Crit Rev Food Sci Nutr 53(4):366–385. doi:10.1080/10408398.2010.536918
May O, Nguyen PT, Arnold FH (2000) Inverting enantioselectivity by directed evolution of hydantoinase for improved production of l-methionine. Nat Biotechnol 18(3):317–320
May O, Verseck S, Bommarius A, Drauz K (2002) Development of dynamic kinetic resolution processes for biocatalytic production of natural and nonnatural l-amino acids. Org Process Res Dev 6(4):452–457
Mello LD, Kubota LT (2002) Review of the use of biosensors as analytical tools in the food and drink industries. Food Chem 77(2):237–256. doi:10.1016/S0308-8146(02)00104-8
MetEx (2014) Press release: Metabolic Explorer in 2013. www.metabolic-explorer.com/images/dynmetex/biblio/fichiers/CP_METEX_2014/PR_Metex_annual_results_2013_29042014.pdf. Accessed 14 Jul 2014
Mitsuhashi S (2014) Current topics in the biotechnological production of essential amino acids, functional amino acids, and dipeptides. Curr Opin Biotechnol 26:38–44
Möckel B, Pfefferle W, Hutmacher K, Rückert C, Kalinowsky J, Pühler A, Binder M, Greisinger D, Thierbach G (2002) Patent to Degussa: Nucleotide sequences which code for the MetY gene. WO2002186132(A1)
Mohammad A, Zehra A (2007) Surfactants modified silica phase for sorption studies of essential amino acids by thin layer chromatography. Colloid Surface A 301(1–3):404–411. doi:10.1016/j.colsurfa.2007.01.004
Mohsin M, Ahmad A (2014) Genetically-encoded nanosensor for quantitative monitoring of methionine in bacterial and yeast cells. Biosens Bioelectron 59C:358–364. doi:10.1016/j.bios.2014.03.066
Mondal S (1993) Influence of cystine on methionine production by Nocardia polychromogenes and Brevibacterium ammoniagenes. Res Ind 38(2):101
Mondal S, Chatterjee SP (1994) Enhancement of methionine production by methionine analog ethionine resistant mutants of Brevibacterium heali. Acta Biotechnol 14(2):199–204
Mondal S, Das Y, Samanta TK, Bhattacharya R, Chatterjee SP (1990) l-Methionine production by Nocardia polychromogenes and Brevibacterium ammoniagenes. Res Ind 35(1):11–14
Mondal S, Das YB, Chatterjee SP (1994a) Improvement of l-methionine production by double auxotrophic mutants of Brevibacterium heali LT(5) and LT(18). Res Ind 39(4):239–241
Mondal S, Das YB, Chatterjee SP (1994b) l-Methionine production by double auxotrophic mutants of an ethionine resistant strain of Brevibacterium heali. Acta Biotechnol 14(1):61–66
Mondal S, Das YB, Chatterjee SP (1996) Methionine production by microorganisms. Folia Microbiologica 41(6):465–472
Moore S, Stein WH (1948) Photometric ninhydrin method for use in the chromatography of amino acids. J Biol Chem 176(1):367–388
Mueller JH (1923) A new sulfur-containing amino-acid isolated from the hydrolytic products of protein. J Biol Chem 56(1):157–169
Mustafi N, Grünberger A, Kohlheyer D, Bott M, Frunzke J (2012) The development and application of a single-cell biosensor for the detection of l-methionine and branched-chain amino acids. Metabolic Engineering 14(4):449–457. doi:10.1016/j.ymben.2012.02.002
Nakagawa S, Mizoguchi H, Ando S, Hayashi M, Ochiai K, Yokoi H, Tateishi N, Senoh A, Ikeda M, Osaki A (2000) Patent to Kyowa Hakko Bio Co., Ltd.: Novel polynucleotides. EP1108790(B1)
Nakamori S, Kobayashi S, Nishimura T, Takagi H (1999) Mechanism of l-methionine overproduction by Escherichia coli: the replacement of Ser-54 by Asn in the MetJ protein causes the derepression of l-methionine biosynthetic enzymes. Appl Microbiol Biotechnol 52(2):179–185
Nakayama K, Sagamihara K, Araki K (1973) Patent to Kyowa Hakko Kogyo Co.: Process for producing l-methionine. US3729381
NOP (2014) Legal Rule § 205.603: Synthetic substances allowed for use in organic livestock production. In: Agricultural Marketing Service, Electronic Code of Federal Regulations Subpart D-Administrative. Part 205—National Organic Program (NOP)
Novus (2012) Animal health through nutrition - Product overview. Novus International, Inc. St. Charles MO. www.novusmethionine.com/Portals/1/1137_v5_EN_GLOBAL_LOWRES.pdf. Accessed 14 July 2014
Nozal MJ, Bernal JL, Toribio ML, Diego JC, Ruiz A (2004) Rapid and sensitive method for determining free amino acids in honey by gas chromatography with flame ionization or mass spectrometric detection. J Chromatogr A 1047(1):137–146
NPOP (2005) Indian: National Programme for Organic Production. Department of Commerce, 6 edn. Ministry of Commerce & Industry, New Delhi. http://www.apeda.gov.in/apedawebsite/organic/ORGANIC_CONTENTS/English_Organic_Sept05.pdf
Nuttall SL, Martin U, Sinclair AJ, Kendall MJ (1998) Glutathione: in sickness and in health. Lancet 351(9103):645–646. doi:10.1016/S0140-6736(05)78428-2
Nwachukwu RES, Ekwealor IA (2009) Methionine-producing Streptomyces species isolated from southern Nigeria soil. Afr J Microbiol Res 3(9):478–481
Osborne TB (1902) Sulphur in protein bodies. J Am Chem Soc 24:140–167
Oz H, Chen T, Neuman M (2008) Methionine deficiency and hepatic injury in a dietary Steatohepatitis model. Dig Dis Sci 53(3):767–776. doi:10.1007/s10620-007-9900-7
Ozulu US, Nwanah OU, Ekwealor CC, Dike SK, Nwikpo CL, Ekwealor IA (2012) A new approach to screening for methionine-producing bacteria. British Microbiol Res J 2(1):36–39. doi:10.9734/BMRJ/2012/989#sthash.5Vhxg5sA.dpuf
Pack M (2004) Aminosäuren in der Tierernährung. Elements - Degussa Sci Newsl 06:30–33
Park SD, Lee JY, Sim SY, Kim Y, Lee HS (2007) Characteristics of methionine production by an engineered Corynebacterium glutamicum strain. Metab Eng 9(4):327–336. doi:10.1016/j.ymben.2007.05.001
Peace RW, Gilani GS (2005) Chromatographic determination of amino acids in foods. J A O A C Int 88(3):877–887
Pelchat ML, Bykowski C, Duke FF, Reed DR (2011) Excretion and perception of a characteristic odor in urine after Asparagus ingestion: a psychophysical and genetic study. Chem Senses 36(1):9–17. doi:10.1093/chemse/bjq081
Perrone CE, Malloy VL, Orentreich DS, Orentreich N (2013) Metabolic adaptations to methionine restriction that benefit health and lifespan in rodents. Exp Gerontol 48(7):654–660. doi:10.1016/j.exger.2012.07.005
Person M, Hazotte A, Elfakir C, Lafosse M (2005) Development and validation of a hydrophilic interaction chromatography-mass spectrometry assay for taurine and methionine in matrices rich in carbohydrates. J Chromatogr A 1081:174–181
Pham CB, Galvez FCF, Padolina WG (1992) Methionine production by batch fermentation from various carbohydrates. ASEAN Food J 7(1):34–37
Phenomenex (2005) EZ:faast amino acid analysis kits - userguide. Phenomenex Inc. Torrance CA. www.phenomenex.com/ViewDocument?id=ezfaast+amino+acid+analysis+kits. Accessed 14 Jul 2014
Pieters S (2002) Commision adopts cartel decision imposing fines in methonine (animal feed) cartel (Degussa and Nippon Soda Company). Competition Polycy Newsletter 3. http://ec.europa.eu/competition/publications/cpn/2002_3_55.pdf. Accessed 14 July 2014
Pina A, Calderon IL, Benitez T (1986) Intergeneric hybrids of Saccharomyces cerevisiae and Zygosaccharomyces fermentati obtained by protoplast fusion. Appl Environ Microbiol 51(5):995–1003
Reershemius HK (2008) Production of l-methionine with Corynebacterium glutamicum. Dissertation, Technical University of Braunschweig, Germany
Rosen H (1957) A modified ninhydrin colorimetric analysis for amino acids. Arch Biochem Biophys 67(1):10–15. doi:10.1016/0003-9861(57)90241-2
Rowbury RJ, Woods DD (1961) Further studies on the repression of methionine synthesis in Escherichia coli. J Gen Microbiol 24:129–144
Roy SK, Mishra AK, Nanda G (1984) Extracellular production of l-methionine by Bacillus megaterium B71 isolated from soil. Curr Sci 53(24):1296–1297
Roy SK, Mishra AK, Nanda G (1985) Methionine production by microorganisms—a review. Trans Bose Res Ins 48:51–57
Roy SK, Biswas SR, Mishra AK, Nanda G (1989) Production and purification of methionine from a multianalog resistant mutant B6US-215 of Bacillus megaterium B71. J Microbial Biotech 4(1):35–41
Sarwar G, Botting HG (1993) Evaluation of liquid chromatographic analysis of nutritionally important amino acids in food and physiological samples. J Chromatogr 615(1):1–22
Sauer U, Mampel J, Schröder H, Häfner S, Zelder O, Herold A, Klopprogge C (2006) Patent to BASF: Microorganisms for producing sulphur-containing compounds. WO2006/008152(A1)
Schneider F, Molck S, Bathe B (2012) Patent to Evonik: Process for the fermentative production of sulphurous amino acids. WO2012/098042(A1)
Schuster R (1980) Determination of free amino acids by high-performance liquid-chromatography. Anal Chem 52(4):617–620
Shakoori FR, Butt AM, Ali NM, Zahid MT, Rehman A, Shakoori AR (2012) Optimization of fermentation media for enhanced amino acids production by bacteria isolated from natural sources. Pak J Zool 44(4):1145–1157
Sharma S, Gomes J (2001) Effect of dissolved oxygen on continuous production of methionine. Chem Eng Technol 24(8):69a–73a
Shewiyo DH, Kaale E, Risha PG, Dejaegher B, Smeyers-Verbeke J, Heyden YV (2012) HPTLC methods to assay active ingredients in pharmaceutical formulations: a review of the method development and validation steps. J Pharm Biomed Anal 66(0):11–23. doi:10.1016/j.jpba.2012.03.034
Sliejkhuis H, Sander JPM (1992) Patent to Gist-Brocades N.V.: Method for preparation or extracting amino acids from manure. EP0287152
Smolnik H-D, Thommel J (1995) Patent to amino: Method for processing industrial discharges. US005384035(A)
Sohal RS, Orr WC (2012) The redox stress hypothesis of aging. Free Radic Biol Med 52(3):539–555
Spackman DH, Stein WH, Moore S (1958) Automatic recording apparatus for use in chromatography of amino acids. Anal Chem 30(7):1190–1206. doi:10.1021/ac60139a006
Srivastava A, Sharma A, Suneetha V (2011) Feather waste biodegradation as a source of amino acids. Eur J Exp Biol 1(2):56–63
Stadtman ER, Van Remmen H, Richardson A, Wehr NB, Levine RL (2005) Methionine oxidation and aging. Biochim Biophys Acta Protein Proteomics 1703(2):135–140
Stahel P, Purdie NG, Cant JP (2014) Use of dietary feather meal to induce histidine deficiency or imbalance in dairy cows and effects on milk composition. J Dairy Sci 97(1):439–445. doi:10.3168/jds. 2013-7269
Sumitomo (2009a) Press release: Sumitomo Chemical announces establishment of Dalian Sumika Jingang Chemicals Co. Ltd. www.sumitomo-chem.co.jp/english/newsreleases/docs/20091210_1.pdf. Accessed 14 Jul 2014
Sumitomo (2009b) Press release: Sumitomo Chemical expands production capacity for feed additive methionine. www.sumitomo-chem.co.jp/english/newsreleases/docs/20090608_1.pdf. Accessed 14 Jul 2014
Syldatk C, May O, Altenbuchner J, Mattes R, Siemann M (1999) Microbial hydantoinases—industrial enzymes from the origin of life? Appl Microbiol Biotechnol 51(3):293–309. doi:10.1007/s002530051395
Tani Y, Lim W-J, Yang H-C (1988) Isolation of l-methionine-enriched mutant of a methylotrophic yeast, Candida biodinii no. 2201. J Ferment Technol 66(2):153–158. doi:10.1016/0385-6380(88)90041-6
Tao SH, Fox MRS, Fry BE, Johnson ML, Lee YH, Tomic JC, Sun SM (1987) Methionine bioavailability of a sulfur-rich protein from Brazil nuts. Fed Proc 46(3):891
Townsend DM, Tew KD, Tapiero H (2004) Sulfur containing amino acids and human disease. Biomed Pharmacother 58(1):47–55. doi:10.1016/j.biopha.2003.11.005
Trötschel C, Deutenberg D, Bathe B, Burkovski A, Kramer R (2005) Characterization of methionine export in Corynebacterium glutamicum. J Bacteriol 187(11):3786–3794
Tsepilova O (2002) In a small industrial city in Russia (Russ. В Поисках Разумной Энергетической Политики. Pro et Contra 7(1):68–83. http://uisrussia.msu.ru/docs/nov/pec/2002/1/ProEtContra_2002_1_04.pdf. Accessed 14 Jul 2014
Tu H, Godfrey L, Sun SM (1998) Expression of the Brazil nut methionine-rich protein and mutants with increased methionine in transgenic potato. Plant Mol Biol 37(5):829–838. doi:10.1023/A:1006098524887
Udaka S (2008) The discovery of Corynebacterium glutamicum and birth of amino acid fermentation industry in Japan. In: Burkovski A (ed) Corynebacteria: genomics and molecular biology. Caister Academic Press, Norwich, pp 1–6
Unibio (2014) Chemical composition of UniProtein®. www.unibio.dk/?page_id=684. Accessed 7 Oct 2014
Usuda Y, Kuruhashi O (2009) Patent to Ajinomoto Co. Inc.: Method for producing l-methionine by fermentation. US7611873(B1)
Van Huis A (2013) Potential of insects as food and feed in assuring food security. Annu Rev Entomol 58(1):563–583. doi:10.1146/annurev-ento-120811-153704
Van Huis A, Van Itterbeeck J, Klunder H, Mertens E, Halloran A, Muir G, Vantomme p (2013) Edible insects—future prospects for food and feed security FAO Forestry Paper. Vol 171. UR, Rome
Van Liempd S, Cabrera D, Mato JM, Falcon-Perez JM (2013) A fast method for the quantitation of key metabolites of the methionine pathway in liver tissue by high-resolution mass spectrometry and hydrophilic interaction ultra-performance liquid chromatography. Anal Bioanal Chem 405(15):5301–5310. doi:10.1007/s00216-013-6883-4
Veldkamp T, G. vD, van Huis A, Lakemond CMM, Ottevanger E, van Boekel MAJS (2012) Insects as a sustainable feed ingrediant in pig and poultry diets: a feasibility study. Livestock Research, Report 638. Wageningen UR, Wageningen. http://www.wageningenur.nl/upload_mm/2/8/0/f26765b9-98b2-49a7-ae43-5251c5b694f6_234247%5B1%5D. Accessed 14 Jul 2014
Venkata Narayana A, Vamsi Priya A, Venkata Nadh R, Swami AVN, Sumalatha B, Vijaya Leela M (2013) Methionine production by coryneform bacteria through fermentation. Research Journal of Pharmaceutical, Biological and Chemical Sciences 4(2):1489–1498
Verseck S (2007) Production of pharmaceutical amino acids. Elements - Degussa Sci Newsl 18:13–15
Vitali L, Della Betta F, Costa AC, Vaz FA, Oliveira MA, Pereira Vistuba J, Favere VT, Micke GA (2014) New multilayer coating using quaternary ammonium chitosan and κ-carrageenan in capillary electrophoresis: application in fast analysis of betaine and methionine. Talanta 123:45–53. doi:10.1016/j.talanta.2014.01.047
Wagner T, Hantke B, Wagner F (1996) Production of l-methionine from d,l-5-(2-methylthioethyl)hydantoin by resting cells of a new mutant strain of Arthrobacter species DSM 7330. J Biotechnol 46(1):63–68
Weckbecker C, Hummel W (2004) Making l from d—in a single cell. Elements-Degussa Sci Newsl 6:34–37. www.degussa.de/de/innovationen/elements.Par.0008. Accessed 14 Jul 2014
Willer H, Lernoud J (eds) (2014) The world of organic agriculture, statistics and emerging trends 2014. FiBL-IFOAM Report. Revised version of February 24, 2014. Researche Institut of Organic Agriculture (FiBL), Frick, and International Federation of Organic Agriculture Movements (IFOAM), Bonn, Frick, Switzerland
Willke T, Hartwich T, Reershemius HK, Jurcheskcu I, Lang S, Vorlop K-D (2010) Ökologisch produziertes Methionin aus Mikroorganismen. In: Rahmann G, Schumacher U. (edn) Landbauforschung, Sonderheft 341: Praxis trifft Forschung-Neues aus der ökologischen Tierhaltung 2010. Johann Heinrich von Thünen-Institut, Braunschweig. http://literatur.vti.bund.de/digbib_extern/dn047235.pdf. Accessed 7 Oct 2014
Winegard HM, Toennies G, Block RJ (1948) Detection of sulfur-containing amino acids on paper chromatograms. Science 108(2810):506–507. doi:10.1126/science.108.2810.506
Woltinger J, Karau A, Leuchtenberger W, Drauz K (2005) Membrane reactors at Degussa. Technology transfer in biotechnology: from Lab to Industry to Production 92:289–316. doi:10.1007/B98909
Woo HM, Park J-B (2014) Recent progress in development of synthetic biology platforms and metabolic engineering of Corynebacterium glutamicum. J Biotechnol 180(0):43–51. doi:10.1016/j.jbiotec.2014.03.003
Work E (1957) Reaction of ninhydrin in acid solution with straight-chain amino acids containing 2 amino groups and its application to the estimation of alpha-epsilon-diaminopimelic acid. Biochem J 67:416–423
Wright A, Orman B (1995) Rapid screening-procedure for methionine levels in maize and soybean. Crop Sci 35(2):584–586
Yamada H, Morinaga Y, Tani Y (1982) Formation of l-methionine by methanol-utilizing bacteria: 1. l-Methionine overproduction by ethionine-resistant mutants of obligate methylotroph strain Om33. Agr Biol Chem Tokyo 46(1):47–55
Yuan YJ, Wang SH, Song ZX, Gao RC (2002) Production of l-methionine by immobilized pellets of Aspergillus oryzae in a packed bed reactor. J Chem Technol Biotechnol 77(5):602–606
Zelder O, Herold A, Klopprogge C, Schroeder H, Haffner S, Heinzle E, Wittmann C, Pero JG, Yocum RR, Patterson T, Williams MK, Herman T (2007) Patent to BASF: Microorganisms with increased efficiency for methionine synthesis. WO2007/020295(A2)
Zelder O, Haffner S, Herold A, Klopprogge C, Schroeder H, Yocum RR, Williams MK (2013) Patent to Evonik: Use of dimethyl disulfide for methionine production in microorganisms. US8399214(B2)
Zhang Y, Yang R, Zhao W (2014) Improving digestibility of feather meal by steam flash explosion. J Agric Food Chem 62(13):2745–2751. doi:10.1021/jf405498k, 2002 #12570
Acknowledgments
I thank Mrs. Dina Fuehrmann for the English language support and Prof. Dr. K.D.-Vorlop for the critical review of the manuscript. I also thank Mr. Denis Jaeger for support in analytical questions.
Conflict of interest
The author declares that he has no conflict of interest.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Willke, T. Methionine production—a critical review. Appl Microbiol Biotechnol 98, 9893–9914 (2014). https://doi.org/10.1007/s00253-014-6156-y
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00253-014-6156-y