Issue 30, 2012

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

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

Supplementary files

Article information

Article type
Paper
Submitted
11 1 2012
Accepted
22 2 2012
First published
19 3 2012

Org. Biomol. Chem., 2012,10, 6217-6229

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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