Biosynthesis of the thiamin-thiazole in eukaryotes: identification of a thiazole tautomer intermediate

J Am Chem Soc. 2008 Aug 27;130(34):11394-8. doi: 10.1021/ja802140a. Epub 2008 Jul 25.


Thiamin thiazole biosynthesis in eukaryotes is still not completely understood. In this report, a late intermediate, tightly bound to the active site of the Saccharomyces cerevisiae thiazole synthase, was identified as an adenylated thiazole tautomer. The reactivity of this unusual compound was evaluated. Its identification provides an additional molecular snapshot of the complex reaction sequence catalyzed by the eukaryotic thiazole synthase and identifies the final step of the thiamin-thiazole biosynthesis.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Adenosine Diphosphate / metabolism
  • Catalysis
  • Catalytic Domain
  • Chromatography, High Pressure Liquid
  • Eukaryotic Cells / enzymology*
  • Isomerism
  • Models, Biological
  • Saccharomyces cerevisiae / cytology
  • Saccharomyces cerevisiae / enzymology*
  • Spectrum Analysis
  • Thiamine / biosynthesis*
  • Thiazoles / metabolism*
  • Time Factors


  • Thiazoles
  • Adenosine Diphosphate
  • Thiamine