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Beilstein J Org Chem. 2012;8:1344-51. Epub 2012 Aug 21.

A macrolactonization approach to the total synthesis of the antimicrobial cyclic depsipeptide LI-F04a and diastereoisomeric analogues.

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1
School of Chemistry, The University of Sydney, 2006, NSW, Australia; Tel: +61-2-93512297;

Abstract

The cyclic peptide core of the antifungal and antibiotic cyclic depsipeptide LI-F04a was synthesised by using a modified Yamaguchi macrolactonization approach. Alternative methods of macrolactonization (e.g., Corey-Nicolaou) resulted in significant epimerization of the C-terminal amino acid during the cyclization reaction. The D-stereochemistry of the alanine residue in the naturally occurring cyclic peptide may be required for the antifungal activity of this natural product.

KEYWORDS:

antifungal; cyclic depsipeptide; epimerization; lipopeptide; macrolactonization; peptides

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