Structure and biosynthetic assembly of gulmirecins, macrolide antibiotics from the predatory bacterium Pyxidicoccus fallax

Chemistry. 2014 Nov 24;20(48):15933-40. doi: 10.1002/chem.201404291. Epub 2014 Oct 6.

Abstract

The gulmirecins constitute a new class of glycosylated macrolides that were isolated from the predatory bacterium Pyxidicoccus fallax HKI 727. Their structures were solved by a combination of NMR spectroscopic experiments and chemical derivatization. Analysis of the annotated gulmirecin gene cluster complemented the configurational assignment and provided insights into the stereochemical course of the biosynthetic assembly. The gulmirecins exhibit strong activity against staphylococci, including methicillin-resistant Staphylococcus aureus, but no cytotoxic effects on human cells.

Keywords: NMR spectroscopy; antibiotics; natural products; polyketides; structure elucidation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / biosynthesis*
  • Anti-Bacterial Agents / chemistry*
  • Anti-Bacterial Agents / pharmacology
  • Bacteriocins / biosynthesis*
  • Bacteriocins / chemistry*
  • Bacteriocins / pharmacology
  • Biological Products / chemistry*
  • Humans
  • Macrolides / chemistry*
  • Macrolides / metabolism*
  • Macrolides / pharmacology
  • Magnetic Resonance Spectroscopy
  • Methicillin-Resistant Staphylococcus aureus / drug effects*
  • Microbial Sensitivity Tests
  • Molecular Sequence Data
  • Molecular Structure
  • Multigene Family
  • Polyketides / chemistry*

Substances

  • Anti-Bacterial Agents
  • Bacteriocins
  • Biological Products
  • Macrolides
  • Polyketides
  • staphylococcin

Associated data

  • GENBANK/KM361622