| Title | Peptide synthesis by unconventional methods | |
| Author | Hernäni L.S. Maia
Department of Chemistry, University of Minho, Gualtar, P-4700 BRAGA, Portugal |
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| Citation | Maia, H.L.S.: Peptide synthesis by unconventional methods, Epitheorese Klin. Farmakol. Farmakokinet. 9(2-3): 79-82 (1995) | |
| Publication Date | 1995 | |
| Full Text Language | English | |
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| Keywords | Peptide synthesis, electrochemistry, group deprotection. | |
| Other Terms | review article | |
| Summary | Some special problems of peptide synthesis can only be resolved by means of specific and eventually uncommon methods. Incorporation of one or more Cα, α-disubstituted glycine residues in a peptide is an example of such problems, where all conventional methods of synthesis usually fail. The use of oxazolinones is still the only valid approach available to make a peptide bond with such amino acids. The four-component condensation has been used with a success in a few particular instances, but its real usefulness lies mainly in the synthesis of Cα, α-disubstituted glycines. Recent progress in organic electrochemistry made this promising technique to find new and valuable applications and has thus been investigated in detail and explored both as a general, unconventional approach to orthogonal protection and as a specific technique to resolve special problems to selective deprotection. Also, recent developments in the use of enzymes in organic media have provided a highly stereo specific but unfortunately a non- general approach to make peptide bonds. Combination with electrochemistry can, however, improve the relevance of both techniques for the search of new solutions to some problems of economical relevance; the unconventional use of the benzoyl group for amine protection is an example. | |
| References | 1. H.L.S. Maia: Ph.D. Thesis, University of Exeter (1970)
2. M.T. Leplawy, D.S. Jones, G.W. Kenner, R.C. Sheppard: Tetrahedron 11: 39 (1960) 3. D.S Jones, G.W. Kenner, J. Preston, R.C. Sheppard: J. Chem. Soc.: 6227 (1965) 4. G. Faust, H. Lang: J. Prakt. Chem. 11: 153 (1960) 5. G.C. Barrett, P.M. Hardy, T.A. Harrow and H.N. Rydon: J. Chem. Soc., Perkin Trans. I: 2634 (1972) 6. I.Z. Siemion, K. Nowak. Roczniki Chem. 34: 1479 (1960) 7. W.J. McGahren, M. Goodman: Tetrahedron 23: 2031 (1967) 8. J.H. Jones, M.J. Witty: J. Chem. Soc., Perkin Trans, I: 3203 (1979) 9. H.L.S. Maia, B. Ridge, H.N. Rydon: J. Chem. Soc., Perkin Trans, I: 96 (1973) 10 A.M. Freitas, H.L.S. Maia: Peptides 1988 (eds. G. Jung and E. Bayer), p. 13 W. de Gruyter, Berlin, 1989 11. T. Yamada, T. Yanagi, Y. Omote, T. Miyazawa, S. Kuwata, M. Sugiura K. Matsumoto: Chem. Express 6: 575 (1991) 12. T. Yamada, T. Yanagi, Y. Omote, T. Miyazawa, S. Kuwata, M. Sugiura, K. Matsumoto: J. Chem. Soc., Chem. Commun.: 1640 (1990) 13. T. Yamada, Y. Omote, T. Miyazawa, S. Kuwata, K. Matsumoto: Peptide Chemistry 1991 (ed. A. Suzuki), p. 367, Protein Research Foundation, Osaka, 1992 14. T. Yamada, Y. Nakamura, T. Miyazawa, S. Kuwata, K. Matsumoto: Chem. Express 8: 161 (1991) 15. H. Heimgarten: Angew. Chem., Int. Ed. Engl. 30: 238 (1991) |
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Online ISSN 1011-6575
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| ΕΤΗΣΙΑ ΣΥΝΔΡΟΜΗ 1995 – ANNUAL SUBSCRIPTION 1995 | |
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