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

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 t...

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Bibliographic Details
Published in:Beilstein journal of organic chemistry 2012-08, Vol.8 (1), p.1344-1351
Main Authors: Cochrane, James R, Yoon, Dong Hee, McErlean, Christopher S P, Jolliffe, Katrina A
Format: Article
Language:English
Subjects:
antifungal
Chemistry
cyclic depsipeptide
epimerization
Full Research Paper
lipopeptide
macrolactonization
peptides
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Summary: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.
ISSN:1860-5397
1860-5397
DOI:10.3762/bjoc.8.154