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

作者：Boyd Derek R^*; Sharma Narain D; Stevenson Paul J; Blain Marine; McRoberts Colin; Hamilton John T G; Argudo Jose M; Mundi Harpinder; Kulakov Leonid A; Allen Christopher C R

来源：Organic and Biomolecular Chemistry, 2011, 9(5): 1479-1490.

DOI：10.1039/c0ob00894j

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).

• 出版日期2011