Total Synthesis and Stereochemical Assignment of the Antimicrobial Lipopeptide Cerexin A1

Stephen A Cochrane, Richard R Surgenor, Kevin M W Khey, John C Vederas

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)5428-31
Number of pages4
JournalOrganic Letters
Volume17
Issue number21
Early online date14 Oct 2015
DOIs
Publication statusPublished - 06 Nov 2015

Keywords

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Bacillus cereus
  • Molecular Structure
  • Peptides
  • Journal Article
  • Research Support, Non-U.S. Gov't

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