The Oxidation of Thiols by Flavoprotein Oxidases: a Biocatalytic Route to Reactive Thiocarbonyls.

T.A. Ewing, W.P. Dijkman, J.J.M. Vervoort, M.W. Fraaije, W.J.H. van Berkel

Research output: Contribution to journalArticleAcademicpeer-review

14 Citations (Scopus)

Abstract

Flavoprotein oxidases are a diverse class of biocatalysts, most of which catalyze the oxidation of C[BOND]O, C[BOND]N, or C[BOND]C bonds. Flavoprotein oxidases that are known to catalyze the oxidation of C[BOND]S bonds are rare, being limited to enzymes that catalyze the oxidative cleavage of thioethers. Herein, we report that various flavoprotein oxidases, previously thought to solely act on alcohols, also catalyze the oxidation of thiols to thiocarbonyls. These results highlight the versatility of enzymatic catalysis and provide a potential biocatalytic route to reactive thiocarbonyl compounds, which have a variety of applications in synthetic organic chemistry.
Original languageEnglish
Pages (from-to)13206-13209
JournalAngewandte Chemie-International Edition
Volume53
Issue number48
DOIs
Publication statusPublished - 2014

Keywords

  • vanillyl-alcohol oxidase
  • streptomyces-coelicolor
  • catalytic mechanism
  • alditol oxidase
  • sulfhydryl oxidase
  • discovery
  • quinones
  • flavins
  • enzyme

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