Identification and biosynthesis of new acyloins from the thermophilic bacterium thermosporothrix hazakensis SK20 - 1T

Jin Soo Park, Noritaka Kagaya, Junko Hashimoto, Miho Izumikawa, Shuhei Yabe, Kazuo Shin-Ya, Makoto Nishiyama, Tomohisa Kuzuyama

Research output: Contribution to journalArticlepeer-review

14 Citations (Scopus)

Abstract

Two new acyloin compounds were isolated from the thermophilic bacterium Thermosporothrix hazakensis SK20-1T. 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. Discovery from a thermophile: Two new acyloins with R configurations at their chiral centers were isolated from the thermophilic bacterium Thermosporothrix hazakensis SK20-1T. These molecules were synthesized from two keto acid substrates by TPP-dependent Thzk0150 enzyme-catalyzed Cï£ ¿C bond condensation.

Original languageEnglish
Pages (from-to)527-532
Number of pages6
JournalChemBioChem
Volume15
Issue number4
DOIs
Publication statusPublished - 2014 Mar 3
Externally publishedYes

Keywords

  • Thermosporothrix hazakensis
  • acyloins
  • biosynthesis
  • enzymes
  • thermophilic bacteria

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Organic Chemistry

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