Identification and biosynthesis of new acyloins from the thermophilic bacterium Thermosporothrix hazakensis SK20-1(T)

Chembiochem. 2014 Mar 3;15(4):527-32. doi: 10.1002/cbic.201300690. Epub 2014 Jan 28.

Abstract

Two new acyloin compounds were isolated from the thermophilic bacterium Thermosporothrix hazakensis SK20-1(T) . Genome sequencing of the bacterium and biochemical studies identified the thiamine diphosphate (TPP)-dependent enzyme Thzk0150, which is involved in the formation of acyloin. Through extensive analysis of the Thzk0150-catalyzed reaction products, we propose a putative reaction mechanism involving two substrates: 4-methyl-2-oxovalerate as an acyl donor and phenyl pyruvate as an acyl acceptor.

Keywords: Thermosporothrix hazakensis; acyloins; biosynthesis; enzymes; thermophilic bacteria.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bacterial Proteins / metabolism
  • Biocatalysis
  • Candida albicans / drug effects
  • Chloroflexi / chemistry*
  • Chloroflexi / metabolism
  • Fatty Alcohols / chemistry
  • Fatty Alcohols / metabolism*
  • Fatty Alcohols / pharmacology
  • Hexanones / chemistry
  • Hexanones / metabolism
  • Hexanones / pharmacology
  • Keto Acids / chemistry
  • Keto Acids / metabolism
  • Phenylpyruvic Acids / chemistry
  • Phenylpyruvic Acids / metabolism

Substances

  • Bacterial Proteins
  • Fatty Alcohols
  • Hexanones
  • Keto Acids
  • Phenylpyruvic Acids
  • sattabacin
  • acyloin
  • alpha-ketoisocaproic acid
  • phenylpyruvic acid