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.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry
Boyd, D. R., Sharma, N. D., Malone, J. F., McIntyre, P. M. A., Stevenson, P. J., Allen, C. C. R., Kwit, M., & Gawronski, J. (2012). Structure, stereochemistry and synthesis of enantiopure cyclohexenone cis-diol bacterial metabolites derived from phenols. Organic and Biomolecular Chemistry, 10(30), 6217-6229. https://doi.org/10.1039/C2OB25079A