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Cleavage of Compounds from Solid Phase by Gaseous Reagents

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Combinatorial Library

Part of the book series: Methods in Molecular Biology™ ((MIMB,volume 201))

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Abstract

The recent interest in organic solid phase synthesis, triggered by the advent of chemical combinatorial methods (17), also accelerated methodology development. Simplification of chemical protocols, their robustness, and amenability to handling large arrays of compounds, prepared by combinatorial/ parallel solid phase synthesis, is one area that witnessed numerous novel contributions. This chapter describes an apparatus and method for gaseous cleavage of compounds from solid phase supports.

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References

  1. Frank R., Heikens W., Heisterberg-Moutsis G., and Blocker H. (1983) A new general approach for the simultaneous chemical synthesis of of large number of oligonucleotides. Segmental solid support. Nucl. Acids Res. 11, 4365–4377.

    Article  CAS  Google Scholar 

  2. Geysen M. H., Meloen R. H., and Barteling S. J. (1984) Use of peptide synthesis to probe viral antigens for epitopes to a resolution of a single amino acid. Proc. Natl. Acad. Sci. USA 81, 3998–4002.

    Article  PubMed  CAS  Google Scholar 

  3. Geysen H. M., Barteling S. J., and Meloen R. H. (1985) Small peptides induced antibody with a sequence and structural requirements for binding antigen comparable to antibodies raised against the native protein. Proc. Natl. Acad. Sci. USA 82, 178.

    Article  PubMed  CAS  Google Scholar 

  4. Frank R. and Döring R. (1988) Simultaneous multiple peptide synthesis under continuous flow conditions on cellulose paper discs as segmental solid supports. Tetrahedron Lett. 29, 6031–6040.

    Article  Google Scholar 

  5. Furka A., Sebestyen F., Asgedom M., and Dibó G. (1991) General method for rapid synthesis of multicomponent peptide mixtures. Int. J. Pept. Protein Res. 37, 487–493.

    Article  PubMed  CAS  Google Scholar 

  6. Houghten R. A., Pinilla C., Blondelle S. E., Appel J. R., Dooley C. T., and Cuervo J. H. (1991) Generation and Use of Synthetic Peptide Combinatorial Libraries for Basic Research and Drug Discovery. Nature 354, 84–86.

    Article  PubMed  CAS  Google Scholar 

  7. Lam K. S., Salmon S. E., Hersh E. M., Hruby V. J., Kazmierski W. M., and Knapp R. J. (1991) A new type of synthetic peptide library for identifying ligandbinding activity. Nature 354, 82–84.

    Article  PubMed  CAS  Google Scholar 

  8. James I. W. (1999) Linkers for solid phase organic synthesis. Tetrahedron 55, 4855–4946.

    Article  CAS  Google Scholar 

  9. Guillier F., Orain D., and Bradley M. (2000) Linkers and cleavage strategies in solid-phase organic synthesis and combinatorial chemsitry. Chem. Rev. 100, 2091–2157.

    Article  PubMed  CAS  Google Scholar 

  10. Wang S. S. (1973) p-Alkoxybenzyl alcohol resin and p-alkoxybenzyloxycarbonylhydrazide resin for solid phase synthesis of protected peptide fragments. J. Am. Chem. Soc. 95, 1328–1333.

    PubMed  CAS  Google Scholar 

  11. Rink H. (1987) Solid-phase synthesis of protected peptide fragments using a trialkoxydiphenyl-methylester resin. Tetrahedron Lett. 28, 3787–3790.

    Article  CAS  Google Scholar 

  12. Bray A. M., Maeji N. J., Jhingran A. G., and Valerio R. M. (1991) Gas Phase Cleavage of Peptides from a Solid Support with Ammonia Vapour—Application in Simultaneous Multiple Peptide Synthesis. Tetrahedron Lett. 32, 6163–6166.

    Article  CAS  Google Scholar 

  13. Flegel M., Rinnova M., Panek Z., Lepsa L., and Blaha I. (1996) Peptides: Chemistry,Structure and Biology, Proc. 14. APS (Kaumaya P. T. P. and Hodges R. S. eds.), Mayflower Scientific Ltd. Kingswinford,119–120

    Google Scholar 

  14. Iyer R. P., Yu D., Xie J., Zhou W., and Agrawal S. (1997) The use of gaseous ammonia for the deprotection and cleavage steps during the solid-phase synthesis of oligonucleotides, and analogs. Bioorg. Med. Chem. Lett. 7, 1443–1448.

    Article  CAS  Google Scholar 

  15. Krchñák V. and Weichsel A. S. (1997) Polymer supported synthesis of diverse perhydro-1,4-diazepine-2, 5-diones. Tetrahedron Lett. 38, 7299–7302.

    Article  Google Scholar 

  16. Jayawickreme C. K., Graminski G. F., Quillan J. M., and Lerner M. R. (1994) Creation and Functional Screening of a Multi-Use Peptide Library. Proc. Natl. Acad. Sci. USA 91, 1614–1618.

    Article  PubMed  CAS  Google Scholar 

  17. Smith J., Gard J., Cummings W., Kaniszai A., and Krchñák V. (1999) Necklace-coded polymer-supported combinatorial synthesis of 2-arylaminobenzimidazoles. J. Comb. Chem. 1, 368–370.

    Article  CAS  Google Scholar 

  18. Lebl M., Krchñák V., Ibrahim G., et al. (1999) Solid-phase synthesis of large tetrahydroisoquinolinone arrays by two different approaches. Synthesis, 1971–1978.

    Google Scholar 

  19. Hebert N., Hannah A. L., and Sutton S. C. (1999) Synthesis of oxadiazoles on solid support. Tetrahedron Lett. 40, 8547–8550.

    Article  CAS  Google Scholar 

  20. Lebl M., Pires J., Poncar P., and Pokorny V. (1999) Evaluation of Gaseous Hydrogen Fluoride as a Convenient Reagent for Parallel Cleavage from the Solid Support. J. Comb. Chem. 1, 474–479.

    Article  PubMed  CAS  Google Scholar 

  21. Krchñák V., Szabo L., and Vagner J. (2000) A solid phase traceless synthesis of quinoxalinones. Tetrahedron Lett. 41, 2835–2838.

    Article  Google Scholar 

  22. Krchñák V., Smith J., and Vagner J. (2001) A solid phase traceless synthesis of 2-arylaminobenzimidazoles. Tetrahedron Lett. 42, 1627–1630.

    Article  Google Scholar 

  23. Krchñák V., Smith J., and Vagner J. (2001) A solid phase traceless synthesis of tetrahydroquinoxalines. Tetrahedron Lett. 42, 2443–2446.

    Article  Google Scholar 

  24. Merrifield R. B. (1963) Solid phase peptide synthesis. I. The synthesis of a tetrapeptide. J. Am. Chem. Soc. 85, 2149–2154.

    Article  CAS  Google Scholar 

  25. Tam J. P., DiMarchi R. D., and Merrifield R. B. (1981) Design and synthesis of a multi-detachable benzhydrylamine resin for solid-phase peptide synthesis. Tetrahedron Lett. 22, 2851–2854.

    Article  CAS  Google Scholar 

  26. Matsueda G. R. and Stewart J. M. (1981) A p-methylbenzhydrylamine resin for improved solid-phase synthesis of peptide amides. Peptides 2, 45–50.

    Article  PubMed  CAS  Google Scholar 

  27. Barlos K., Gatos D., Kallitsis I., Papaioannou D., and Sotiriou P. (1988) Application of 4-polystyryltriphenylmethyl chloride to the syntheses of peptides and amino acid derivatives. Liebigs Ann. Chem. 1988, 1079–1081.

    Article  Google Scholar 

  28. Barlos K., Chatzi O., Gatos D., and Stavropoulos G. (1991) 2-Chlorotrityl chloride resin—Studies on Anchoring of Fmoc-Amino Acids and Peptide Cleavage. Int. J. Pept. Protein Res. 37, 513–520.

    PubMed  CAS  Google Scholar 

  29. Sheppard R. C. and Williams B. J. (1982) Acid-labile resin linkage agents for use in solid phase peptide synthesis. Int. J. Pept. Protein Res. 20, 451–454.

    Article  PubMed  CAS  Google Scholar 

  30. Mergler M. (1988) Peptide synthesis by combinaiton of solid-phase and solution methods: A new very acid-labile anchor group for the solid phase synthesis of fully protected fragments. Tetrahedron Lett. 29, 4005

    Article  CAS  Google Scholar 

  31. Albericio F., Kneibcordonier N., Biancalana S., et al. (1990) Preparation and Application of the 5-(4-(9-Fluorenylmethyloxycarbonyl)aminomethyl-3,5-Dimethoxyphenoxy) valeric acid (Pal) handle for the solid-phase synthesis of C-terminal peptide amides under mild conditions. J. Org. Chem. 55, 3730–3743.

    Article  CAS  Google Scholar 

  32. Fivush A. M. and Willson T. M. (1997) AMEBA: An acid sensitive aldehyde resin for solid phase synthesis. Tetrahedron Lett. 38, 7151–7154.

    Article  CAS  Google Scholar 

  33. Jensen K. J., Alsina J., Songster M. F., Vagner J., Albericio F., and Barany G. (1998) Backbone amide linker (BAL) strategy for solid-phase synthesis of C-terminal modified and cyclic petides. J. Am. Chem. Soc. 120, 5441–5452.

    Article  CAS  Google Scholar 

  34. Smith J. and Krchñák V. (1999) A solid phase traceless synthesis of benzimidazoles with three combinatorial steps. Tetrahedron Lett. 40, 7633–7636.

    Article  CAS  Google Scholar 

  35. Lebl M. and Krchñák V. (1998) Innovation & Perspectives in Solid Phase Synthesis & Combinatorial Libraries (Epton R. ed.), Mayflower Scientific Limited, Birmingham, UK, 43–46.

    Google Scholar 

  36. Krchñák V. (1998) Semi-automated high throughput combinatorial solid-phase organic synthesis. Biotechnol. Bioeng. (Comb. Chem.) 61, 135–141.

    Article  Google Scholar 

  37. Kerschen A., Kaniszai A., Botros I., and Krchñák V. (1999) Apparatus and method for cleavage of compounds from solid support by gaseous reagents. J. Comb. Chem. 1, 480–484.

    Article  CAS  Google Scholar 

  38. Boojamra C. G., Burow K. M., and Ellman J. A. (1995) An expedient and highyielding method for the solid-phase synthesis of diverse 1,4-benzodiazepine-2,5-diones. J. Org. Chem. 60, 5742–5743.

    Article  CAS  Google Scholar 

  39. Jensen K. J., Songster M. F., Vagner J., Alsina J., Albericio F., and Barany G. (1996) Peptides: Chemistry, Structure and Biology (Kaumaya P. T. P. and Hodges R. S. eds.), Mayflower Scientific Ltd. Birmingham, UK, 30, 31.

    Google Scholar 

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Krchňák, V. (2002). Cleavage of Compounds from Solid Phase by Gaseous Reagents. In: English, L.B. (eds) Combinatorial Library. Methods in Molecular Biology™, vol 201. Springer, Totowa, NJ. https://doi.org/10.1385/1-59259-285-6:61

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  • DOI: https://doi.org/10.1385/1-59259-285-6:61

  • Publisher Name: Springer, Totowa, NJ

  • Print ISBN: 978-0-89603-980-3

  • Online ISBN: 978-1-59259-285-2

  • eBook Packages: Springer Protocols

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