Journal
CURRENT MEDICINAL CHEMISTRY
Volume 11, Issue 21, Pages 2799-2822Publisher
BENTHAM SCIENCE PUBL LTD
DOI: 10.2174/0929867043364108
Keywords
amino acid; N-methylation; C alpha-methylation; organic synthesis; structure; backbone constraint; peptide; biological activity
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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.
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