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Issue 30, 2012
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Structure, stereochemistry and synthesis of enantiopure cyclohexenone cis-diol bacterial metabolites derived from phenols

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Abstract

Biotransformation of 3-substituted and 2,5-disubstituted phenols, using whole cells of P. putida UV4, yielded cyclohexenone cis-diols as single enantiomers; their structures and absolute configurations have been determined by NMR and ECD spectroscopy, X-ray crystallography, and stereochemical correlation involving a four step chemoenzymatic synthesis from the corresponding cis-dihydrodiol metabolites. An active site model has been proposed, to account for the formation of enantiopure cyclohexenone cis-diols with opposite absolute configurations.

Graphical abstract: Structure, stereochemistry and synthesis of enantiopure cyclohexenone cis-diol bacterial metabolites derived from phenols

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Publication details

The article was received on 11 Jan 2012, accepted on 22 Feb 2012 and first published on 19 Mar 2012


Article type: Paper
DOI: 10.1039/C2OB25079A
Citation: Org. Biomol. Chem., 2012,10, 6217-6229
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    Structure, stereochemistry and synthesis of enantiopure cyclohexenone cis-diol bacterial metabolites derived from phenols

    D. R. Boyd, N. D. Sharma, J. F. Malone, P. B. A. McIntyre, P. J. Stevenson, C. C. R. Allen, M. Kwit and J. Gawronski, Org. Biomol. Chem., 2012, 10, 6217
    DOI: 10.1039/C2OB25079A

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