Electrochemically mediated enantioselective reduction of chiral sulfoxides
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| 024 | 7 | 0 | |a 10.1007/s00775-014-1215-5 |2 doi |
| 035 | |a (NATIONALLICENCE)springer-10.1007/s00775-014-1215-5 | ||
| 245 | 0 | 0 | |a Electrochemically mediated enantioselective reduction of chiral sulfoxides |h [Elektronische Daten] |c [Kuan-I. Chen, Victoria Challinor, Linda Kielmann, Philip Sharpe, James De Voss, Ulrike Kappler, Alastair McEwan, Paul Bernhardt] |
| 520 | 3 | |a 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. Graphical Abstract: | |
| 540 | |a SBIC, 2014 | ||
| 690 | 7 | |a Molybdenum |2 nationallicence | |
| 690 | 7 | |a Voltammetry |2 nationallicence | |
| 690 | 7 | |a Enzyme |2 nationallicence | |
| 690 | 7 | |a Chiral sulfoxide |2 nationallicence | |
| 700 | 1 | |a Chen |D Kuan-I |u School of Chemistry and Molecular Biosciences, University of Queensland, 4072, Brisbane, Australia |4 aut | |
| 700 | 1 | |a Challinor |D Victoria |u School of Chemistry and Molecular Biosciences, University of Queensland, 4072, Brisbane, Australia |4 aut | |
| 700 | 1 | |a Kielmann |D Linda |u School of Chemistry and Molecular Biosciences, University of Queensland, 4072, Brisbane, Australia |4 aut | |
| 700 | 1 | |a Sharpe |D Philip |u School of Chemistry and Molecular Biosciences, University of Queensland, 4072, Brisbane, Australia |4 aut | |
| 700 | 1 | |a De Voss |D James |u School of Chemistry and Molecular Biosciences, University of Queensland, 4072, Brisbane, Australia |4 aut | |
| 700 | 1 | |a Kappler |D Ulrike |u School of Chemistry and Molecular Biosciences, University of Queensland, 4072, Brisbane, Australia |4 aut | |
| 700 | 1 | |a McEwan |D Alastair |u School of Chemistry and Molecular Biosciences, University of Queensland, 4072, Brisbane, Australia |4 aut | |
| 700 | 1 | |a Bernhardt |D Paul |u School of Chemistry and Molecular Biosciences, University of Queensland, 4072, Brisbane, Australia |4 aut | |
| 773 | 0 | |t JBIC Journal of Biological Inorganic Chemistry |d Springer Berlin Heidelberg |g 20/2(2015-03-01), 395-402 |x 0949-8257 |q 20:2<395 |1 2015 |2 20 |o 775 | |
| 856 | 4 | 0 | |u https://doi.org/10.1007/s00775-014-1215-5 |q text/html |z Onlinezugriff via DOI |
| 898 | |a BK010053 |b XK010053 |c XK010000 | ||
| 900 | 7 | |a Metadata rights reserved |b Springer special CC-BY-NC licence |2 nationallicence | |
| 908 | |D 1 |a research-article |2 jats | ||
| 949 | |B NATIONALLICENCE |F NATIONALLICENCE |b NL-springer | ||
| 950 | |B NATIONALLICENCE |P 856 |E 40 |u https://doi.org/10.1007/s00775-014-1215-5 |q text/html |z Onlinezugriff via DOI | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Chen |D Kuan-I |u School of Chemistry and Molecular Biosciences, University of Queensland, 4072, Brisbane, Australia |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Challinor |D Victoria |u School of Chemistry and Molecular Biosciences, University of Queensland, 4072, Brisbane, Australia |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Kielmann |D Linda |u School of Chemistry and Molecular Biosciences, University of Queensland, 4072, Brisbane, Australia |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Sharpe |D Philip |u School of Chemistry and Molecular Biosciences, University of Queensland, 4072, Brisbane, Australia |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a De Voss |D James |u School of Chemistry and Molecular Biosciences, University of Queensland, 4072, Brisbane, Australia |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Kappler |D Ulrike |u School of Chemistry and Molecular Biosciences, University of Queensland, 4072, Brisbane, Australia |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a McEwan |D Alastair |u School of Chemistry and Molecular Biosciences, University of Queensland, 4072, Brisbane, Australia |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Bernhardt |D Paul |u School of Chemistry and Molecular Biosciences, University of Queensland, 4072, Brisbane, Australia |4 aut | ||
| 950 | |B NATIONALLICENCE |P 773 |E 0- |t JBIC Journal of Biological Inorganic Chemistry |d Springer Berlin Heidelberg |g 20/2(2015-03-01), 395-402 |x 0949-8257 |q 20:2<395 |1 2015 |2 20 |o 775 | ||