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

Flavoprotein oxidases are a diverse class of biocatalysts, most of which catalyze the oxidation of CO, CN, or CC bonds. Flavoprotein oxidases that are known to catalyze the oxidation of CS bonds are rare, being limited to enzymes that catalyze the oxidative cleavage of thioethers. Herein, we rep...

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Published inAngewandte Chemie (International ed.) Vol. 53; no. 48; pp. 13206 - 13209
Main Authors Ewing, Tom A., Dijkman, Willem P., Vervoort, Jacques M., Fraaije, Marco W., van Berkel, Willem J. H.
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 24.11.2014
WILEY‐VCH Verlag
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
alditol oxidase
biocatalysis
Catalysis
catalytic mechanism
Cleavage
discovery
enzyme
Enzymes
flavins
flavoprotein oxidases
Flavoproteins - chemistry
kinetics
Organic chemistry
Oxidase
Oxidation
Oxidation-Reduction
oxidoreductases
Oxidoreductases - chemistry
Pharmaceutical industry
Players
quinones
streptomyces-coelicolor
Sulfhydryl Compounds - chemistry
sulfhydryl oxidase
thiol oxidation
Thiols
vanillyl-alcohol oxidase
Versatility
oxidoreductases
flavoprotein oxidases
kinetics
biocatalysis
thiol oxidation
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Summary:Flavoprotein oxidases are a diverse class of biocatalysts, most of which catalyze the oxidation of CO, CN, or CC bonds. Flavoprotein oxidases that are known to catalyze the oxidation of C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. An all‐around player: Numerous classical flavin‐dependent alcohol oxidases, such as alditol oxidase (AldO), which are well‐known for their activity towards CO and CN bonds, can also catalyze the oxidation of thiols (see picture). This method provides a potential biocatalytic route to reactive thiocarbonyl compounds.
Bibliography:ark:/67375/WNG-CVNCM026-N
ArticleID:ANIE201407520
Dutch Ministry of Economic Affairs, Agriculture, and Innovation (EL&I)
istex:1C9443DDF709F1087270751DB87131B0A7508FB7
This work was carried out within the BE-Basic R&D Program, for which an FES subsidy was granted from the Dutch Ministry of Economic Affairs, Agriculture, and Innovation (EL&I).
BE-Basic R&D Program
These authors contributed equally to this work.
This work was carried out within the BE‐Basic R&D Program, for which an FES subsidy was granted from the Dutch Ministry of Economic Affairs, Agriculture, and Innovation (EL&I).
ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201407520