Tauramamide, a lipopeptide antibiotic produced in culture by Brevibacillus laterosporus isolated from a marine habitat: structure elucidation and synthesis

J Nat Prod. 2007 Dec;70(12):1850-3. doi: 10.1021/np070209r. Epub 2007 Nov 29.

Abstract

Tauramamide (1), a new lipopeptide antibiotic, is produced by cultures of the marine bacterial isolate Brevibacillus laterosporus PNG276 obtained from Papua New Guinea. Tauramamide was isolated as its methyl and ethyl esters 2 and 3, whose structures were elucidated by analysis of NMR, MS, and chemical degradation data. A total synthesis of tauramamide (1) and tauramamide ethyl ester (3) confirmed the structure proposed from spectroscopic analysis and provided the natural product for antimicrobial testing. Tauramamide (1) and ethyl ester 3 show potent and relatively selective inhibition of pathogenic Enterococcus sp.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification*
  • Anti-Bacterial Agents / pharmacology*
  • Bacillus / chemistry*
  • Enterococcus / drug effects*
  • Lipopeptides
  • Lipoproteins / chemistry
  • Lipoproteins / isolation & purification*
  • Lipoproteins / pharmacology*
  • Marine Biology
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Papua New Guinea

Substances

  • Anti-Bacterial Agents
  • Lipopeptides
  • Lipoproteins
  • tauramamide