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

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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 restrict 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; backbone constraint; biological activity; methylation; n-methylation; organic synthesis; peptide; structure

Document Type: Review Article

DOI: http://dx.doi.org/10.2174/0929867043364108

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

Publication date: November 1, 2004

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  • Current Medicinal Chemistry covers all the latest and outstanding developments in medicinal chemistry and rational drug design. Each issue contains a series of timely in-depth reviews written by leaders in the field covering a range of the current topics in medicinal chemistry. Current Medicinal Chemistry is an essential journal for every medicinal chemist who wishes to be kept informed and up-to-date with the latest and most important developments.
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