title: N- and Calpha-methylation in biologically active peptides: synthesis, structural and functional aspects.
abstract: Numerous backbone constraints can be used to develop pseudopeptides or pseudomimetics of biologically active peptides. Among those, N- and Calpha-methyl amino acids that can be incorporated by solid-phase peptide synthesis in a bioactive sequence represent important tools to restrict phi and psi angles of peptide backbone. This review will focus on the chemical syntheses of N- and Calpha-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.
authors.affiliation: UMR 7613 CNRS-Université Pierre & Marie Curie, Structure and Function of Bioactive Molecules, Case courrier 182, 4 place Jussieu, 75005 Paris, France. sagan@ccr.jussieu.fr
authors.forename: Sandrine
authors.initials: S
authors.lastname: Sagan
authors.forename: Philippe
authors.initials: P
authors.lastname: Karoyan
authors.forename: Olivier
authors.initials: O
authors.lastname: Lequin
authors.forename: Gérard
authors.initials: G
authors.lastname: Chassaing
authors.forename: Solange
authors.initials: S
authors.lastname: Lavielle
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism; D000818:Animals; D006801:Humans; D008745:Methylation; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*
chemical_list: D000596:Amino Acids; D010455:Peptides