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

12 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

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Flavoproteins
Sulfhydryl Compounds
Oxidoreductases
Oxidation
Biocatalysts
Sulfides
Enzymes
Catalysis
Alcohols

Keywords

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

Cite this

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title = "The Oxidation of Thiols by Flavoprotein Oxidases: a Biocatalytic Route to Reactive Thiocarbonyls.",
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.",
keywords = "vanillyl-alcohol oxidase, streptomyces-coelicolor, catalytic mechanism, alditol oxidase, sulfhydryl oxidase, discovery, quinones, flavins, enzyme",
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The Oxidation of Thiols by Flavoprotein Oxidases: a Biocatalytic Route to Reactive Thiocarbonyls. / Ewing, T.A.; Dijkman, W.P.; Vervoort, J.J.M.; Fraaije, M.W.; van Berkel, W.J.H.

In: Angewandte Chemie-International Edition, Vol. 53, No. 48, 2014, p. 13206-13209.

Research output: Contribution to journalArticleAcademicpeer-review

TY - JOUR

T1 - The Oxidation of Thiols by Flavoprotein Oxidases: a Biocatalytic Route to Reactive Thiocarbonyls.

AU - Ewing, T.A.

AU - Dijkman, W.P.

AU - Vervoort, J.J.M.

AU - Fraaije, M.W.

AU - van Berkel, W.J.H.

PY - 2014

Y1 - 2014

N2 - 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.

AB - 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.

KW - vanillyl-alcohol oxidase

KW - streptomyces-coelicolor

KW - catalytic mechanism

KW - alditol oxidase

KW - sulfhydryl oxidase

KW - discovery

KW - quinones

KW - flavins

KW - enzyme

U2 - 10.1002/anie.201407520

DO - 10.1002/anie.201407520

M3 - Article

VL - 53

SP - 13206

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JO - Angewandte Chemie-International Edition

JF - Angewandte Chemie-International Edition

SN - 1433-7851

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