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

Derek R. Boyd, Narain D. Sharma, John F. Malone, Peter M. A. McIntyre, Paul J. Stevenson, Christopher C. R. Allen, Marcin Kwit, Jacek Gawronski

Research output: Contribution to journalArticle

8 Citations (Scopus)

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.
Original languageEnglish
Pages (from-to)6217-6229
Number of pages13
JournalOrganic and Biomolecular Chemistry
Volume10
Issue number30
Early online date19 Mar 2012
DOIs
Publication statusPublished - 2012

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Biochemistry

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