Mechanistic studies of the biosynthesis of 2-thiosugar: Evidence for the formation of an enzyme-bound 2-ketohexose intermediate in BexX-catalyzed reaction

Eita Sasaki, Hung Wen Liu

Research output: Contribution to journalArticlepeer-review

13 Citations (Scopus)

Abstract

The first mechanistic insight into 2-thiosugar production in an angucycline-type antibiotic, BE-7585A, is reported. d-Glucose 6-phosphate was identified as the substrate for the putative thiosugar biosynthetic protein, BexX, by trapping the covalently bonded enzyme-substrate intermediate. The site-specific modification at K110 residue was determined by mutagenesis studies and LC-MS/MS analysis. A key intermediate carrying a keto functionality was confirmed to exist in the enzyme-substrate complex. These results suggest that the sulfur insertion mechanism in 2-thiosugar biosynthesis shares similarities with that for thiamin biosynthesis.

Original languageEnglish
Pages (from-to)15544-15546
Number of pages3
JournalJournal of the American Chemical Society
Volume132
Issue number44
DOIs
Publication statusPublished - 2010 Nov 10
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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