Organic and Biomolecular Chemistry p. 6217 - 6229 (2012)
Update date:2022-08-04
Topics: Synthesis Stereochemistry Structure Enantiopure Bacterial metabolites Cyclohexenone
Boyd, Derek R.
Sharma, Narain D.
Malone, John F.
McIntyre, Peter B. A.
Stevenson, Paul J.
Allen, Christopher C. R.
Kwit, Marcin
Gawronski, Jacek
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.
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