Synthesis and assignment of stereochemistry of the antibacterial cyclic peptide xenematide

Org Biomol Chem. 2011 Jan 7;9(1):236-42. doi: 10.1039/c0ob00315h. Epub 2010 Oct 15.

Abstract

The synthesis of the antimicrobial cyclic peptide xenematide was accomplished by Fmoc solid phase peptide synthesis and the key esterification reaction was achieved using a modified Yamaguchi esterification. Comparison of the optical rotation and NMR data of the synthesized diastereomers to that of the natural product confirmed the structure of xenematide to be PA-L-[Thr-L-Trp-D-Trp-β-Ala]. (PA = phenylacetyl).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry*
  • Depsipeptides / chemical synthesis
  • Depsipeptides / chemistry*
  • Molecular Structure
  • Stereoisomerism

Substances

  • Anti-Bacterial Agents
  • Depsipeptides
  • xenematide