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Total Synthesis and Stereochemical Assignment of the Antimicrobial Lipopeptide Cerexin A1
Stephen A Cochrane1, Richard R Surgenor1, Kevin M W Khey1
1Department of Chemistry, University of Alberta , Edmonton, Alberta T6G 2G2, Canada.
Abstract:
The isolation and total synthesis of the antimicrobial lipopeptide cerexin A1 is reported. This synthesis includes the preparation of orthogonally protected γ-hydroxylysine, utilizing a nitrile Reformatsky-type reaction as a key step to yield both diastereomers more efficiently than previously reported methods. The configuration of the β-hydroxyl in the lipid tail was determined by the use of a modified Ohrui-Akasaka approach. Furthermore, new cerexin analogues from Bacillus mycoides ATCC 21929 were isolated and characterized, revealing an ε-amino succinylation of a hydroxylysine residue that is unusual in a nonribosomal peptide synthetase product.
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