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

[ Vol. 11 , Issue. 21 ]

Author(s):

Sandrine Sagan, Philippe Karoyan, Olivier Lequin, Gerard Chassaing and Solange Lavielle   Pages 2799 - 2822 ( 24 )

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

Affiliation:

, , , , UMR 7613 CNRSUniversite Pierre&Marie Curie, Structure and Function of Bioactive Molecules, Case courrier 182, 4 place Jussieu, 75005 Paris, France.



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