Electrochemically mediated enantioselective reduction of chiral sulfoxides

Chen, Kuan I., Challinor, Victoria L., Kielmann, Linda, Sharpe, Philip C., De Voss, James J., Kappler, Ulrike, McEwan, Alastair G. and Bernhardt, Paul V. (2014) Electrochemically mediated enantioselective reduction of chiral sulfoxides. Journal of Biological Inorganic Chemistry, 20 2: 395-402. doi:10.1007/s00775-014-1215-5

Author Chen, Kuan I.
Challinor, Victoria L.
Kielmann, Linda
Sharpe, Philip C.
De Voss, James J.
Kappler, Ulrike
McEwan, Alastair G.
Bernhardt, Paul V.
Title Electrochemically mediated enantioselective reduction of chiral sulfoxides
Journal name Journal of Biological Inorganic Chemistry   Check publisher's open access policy
ISSN 0949-8257
Publication date 2014-11-20
Year available 2014
Sub-type Article (original research)
DOI 10.1007/s00775-014-1215-5
Open Access Status
Volume 20
Issue 2
Start page 395
End page 402
Total pages 8
Place of publication Heidelberg, Germany
Publisher Springer
Collection year 2015
Language eng
Formatted 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.
Keyword Molybdenum
Chiral sulfoxide
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ
Additional Notes Published online ahead of print 20 November 2014.

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2015 Collection
School of Chemistry and Molecular Biosciences
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Created: Fri, 28 Nov 2014, 10:40:44 EST by Mrs Louise Nimwegen on behalf of School of Chemistry & Molecular Biosciences