Enzyme-catalysed synthesis and absolute configuration assignments of cis-dihydrodiol metabolites from 1,4-disubstituted benzenes

Derek Boyd, Narain Sharma, Gregory Coen, Peter Gray, John Malone, J. Gawronski

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

A series of ten cis-dihydro-diol metabolites has been obtained by bacterial biotransformation of the corresponding 1,4-disubstituted benzene substrates using Pseudomonas putida UV4, a source of toluene dioxygenase (TDO). Their enantiomeric excess (ee) values have been established using chiral stationary phase HPLC and H-1 NMR spectroscopy. Absolute configurations of the majority of cis-dihydrodiols have been established using stereochemical correlation and X-ray crystallography and the remainder have been tentatively assigned using NMR spectroscopic methods but finally confirmed by circular dichroism (CD) spectroscopy. These configurational assignments support and extend the validity of an empirical model, previously used to predict the preferred stereochemistry of TDO-catalysed cis-dihydroxylation of ten 1,4-disubstituted benzene substrates, to more than twenty-five examples.
Original languageEnglish
Pages (from-to)5804-5811
Number of pages8
JournalChemistry-a European Journal
Volume13 (20)
Issue number20
DOIs
Publication statusPublished - Apr 2007

ASJC Scopus subject areas

  • Chemistry(all)

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