Complete characterization of the seventeen step moenomycin biosynthetic pathway

Biochemistry. 2009 Sep 22;48(37):8830-41. doi: 10.1021/bi901018q.

Abstract

The moenomycins are phosphoglycolipid antibiotics produced by Streptomyces ghanaensis and related organisms. The phosphoglycolipids are the only known active site inhibitors of the peptidoglycan glycosyltransferases, an important family of enzymes involved in the biosynthesis of the bacterial cell wall. Although these natural products have exceptionally potent antibiotic activity, pharmacokinetic limitations have precluded their clinical use. We previously identified the moenomycin biosynthetic gene cluster in order to facilitate biosynthetic approaches to new derivatives. Here, we report a comprehensive set of genetic and enzymatic experiments that establish functions for the 17 moenomycin biosynthetic genes involved in the synthesis of moenomycin and variants. These studies reveal the order of assembly of the full molecular scaffold and define a subset of seven genes involved in the synthesis of bioactive analogues. This work will enable both in vitro and fermentation-based reconstitution of phosphoglycolipid scaffolds so that chemoenzymatic approaches to novel analogues can be explored.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Anti-Bacterial Agents / biosynthesis*
  • Anti-Bacterial Agents / chemistry*
  • Bambermycins / biosynthesis*
  • Bambermycins / chemistry*
  • Drug Resistance, Bacterial
  • Gene Deletion
  • Genes, Bacterial*
  • Glycolipids / biosynthesis
  • Glycolipids / chemistry
  • Multigene Family*
  • Peptidoglycan Glycosyltransferase / antagonists & inhibitors
  • Peptidoglycan Glycosyltransferase / chemistry
  • Peptidoglycan Glycosyltransferase / genetics
  • Phospholipids / biosynthesis
  • Phospholipids / chemistry
  • Streptomyces / metabolism
  • Streptomyces lividans / metabolism

Substances

  • Anti-Bacterial Agents
  • Glycolipids
  • Phospholipids
  • Bambermycins
  • moenomycin A
  • Peptidoglycan Glycosyltransferase