Abstract
Numerous backbone constraints can be used to develop pseudopeptides or pseudomimetics of biologically active peptides. Among those, N- and Cα-methyl amino acids that can be incorporated by solidphase peptide synthesis in a bioactive sequence represent important tools to restrictφ and ψ angles of peptide backbone. This review will focus on the chemical syntheses of N- and Cα-methyl amino acids, their effects on peptide conformation and structure, and their role on the peptide stability towards enzymatic degradation and on the biological activities of the resulting analogues.
Keywords: amino acid, n-methylation, methylation, organic synthesis, structure, backbone constraint, peptide, biological activity
Current Medicinal Chemistry
Title: N- and Cα-Methylation in Biologically Active Peptides: Synthesis, Structural and Functional Aspects
Volume: 11 Issue: 21
Author(s): Sandrine Sagan, Philippe Karoyan, Olivier Lequin, Gerard Chassaing and Solange Lavielle
Affiliation:
Keywords: amino acid, n-methylation, methylation, organic synthesis, structure, backbone constraint, peptide, biological activity
Abstract: Numerous backbone constraints can be used to develop pseudopeptides or pseudomimetics of biologically active peptides. Among those, N- and Cα-methyl amino acids that can be incorporated by solidphase peptide synthesis in a bioactive sequence represent important tools to restrictφ and ψ angles of peptide backbone. This review will focus on the chemical syntheses of N- and Cα-methyl amino acids, their effects on peptide conformation and structure, and their role on the peptide stability towards enzymatic degradation and on the biological activities of the resulting analogues.
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Cite this article as:
Sagan Sandrine, Karoyan Philippe, Lequin Olivier, Chassaing Gerard and Lavielle Solange, N- and Cα-Methylation in Biologically Active Peptides: Synthesis, Structural and Functional Aspects, Current Medicinal Chemistry 2004; 11 (21) . https://dx.doi.org/10.2174/0929867043364108
DOI https://dx.doi.org/10.2174/0929867043364108 |
Print ISSN 0929-8673 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-533X |
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