N- and Cα-Methylation in Biologically Active Peptides: Synthesis, Structural and Functional Aspects

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.

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