Electrochemically mediated enantioselective reduction of chiral sulfoxides

Kuan-I Chen, Victoria Louise Challinor, Linda Kielmann, Philip C Sharpe, James J De Voss, Ulrike Kappler, Alastair G McEwan, Paul V Bernhardt

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

7 Citationer (Scopus)

Abstract

The respiratory DMSO reductase from Rhodobacter capsulatus catalyzes the reduction of dimethyl sulfoxide to dimethyl sulfide. Herein, we have utilized this Mo enzyme as an enantioselective catalyst to generate optically pure sulfoxides (methyl p-tolyl sulfoxide, methyl phenyl sulfoxide and phenyl vinyl sulfoxide) from racemic starting materials. A hexaaminecobalt coordination compound in its divalent oxidation state was employed as the mediator of electron transfer between the working electrode and DMSO reductase to continually reactivate the enzyme after turnover. In all cases, chiral HPLC analysis of the reaction mixture revealed that the S-sulfoxide was reduced more rapidly leading to enrichment or isolation of the R isomer.

OriginalsprogEngelsk
TidsskriftJournal of Biological Inorganic Chemistry
Vol/bind20
Udgave nummer2
Sider (fra-til)395-402
Antal sider8
ISSN0949-8257
DOI
StatusUdgivet - 2015
Udgivet eksterntJa

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