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

doi:10.1002/anie.201407520

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 journal › Article › Academic › peer-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 language	English
Pages (from-to)	13206-13209
Journal	Angewandte Chemie-International Edition
Volume	53
Issue number	48
DOIs	https://doi.org/10.1002/anie.201407520
Publication status	Published - 2014

Keywords

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

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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",

author = "T.A. Ewing and W.P. Dijkman and J.J.M. Vervoort and M.W. Fraaije and {van Berkel}, W.J.H.",

year = "2014",

doi = "10.1002/anie.201407520",

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pages = "13206--13209",

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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

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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

EP - 13209

JO - Angewandte Chemie-International Edition

JF - Angewandte Chemie-International Edition

SN - 1433-7851

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