Dioxygenase-catalysed cis-dihydroxylation of meta-substituted phenols to yield cyclohexenone cis-diol and derived enantiopure cis-triol metabolites

Derek Boyd, Narain Sharma, Paul Stevenson, M. Blain, C. McRoberts, John Hamilton, J.M. Argudo, H. Mundi, Leonid Kulakov, Christopher Allen

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

cis-Dihydroxylation of meta-substituted phenol (m-phenol) substrates, to yield the corresponding cyclohexenone cis-diol metabolites, was catalysed by arene dioxygenases present in mutant and recombinant bacterial strains. The presence of cyclohexenone cis-diol metabolites and several of their cyclohexene and cyclohexane cis-triol derivatives was detected by LC-TOFMS analysis and confirmed by NMR spectroscopy. Structural and stereochemical analyses of chiral ketodiol bioproducts, was carried out using NMR and CD spectroscopy and stereochemical correlation methods. The formation of enantiopure cyclohexenone cis-diol metabolites is discussed in the context of postulated binding interactions of the m-phenol substrates at the active site of toluene dioxygenase (TDO).
Original languageEnglish
Pages (from-to)1479-1490
Number of pages12
JournalOrganic and Biomolecular Chemistry
Volume9
Issue number5
DOIs
Publication statusPublished - 01 Mar 2011

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Biochemistry

Fingerprint Dive into the research topics of 'Dioxygenase-catalysed cis-dihydroxylation of meta-substituted phenols to yield cyclohexenone cis-diol and derived enantiopure cis-triol metabolites'. Together they form a unique fingerprint.

  • Cite this