Abstract
Toluene dioxygenase-catalysed cis-dihydroxylations of substituted aniline and phenol substrates, with a Pseudomonas putida UV4 mutant strain and an Escherichia coli pCL-4t recombinant strain, yielded identical arene cis-dihydrodiols, which were isolated as the preferred cyclohex-2-en-1-one cis-diol tautomers. These cis-diol metabolites were predicted by preliminary molecular docking studie, of anilines and phenols, at the active site of toluene dioxygenase Further biotransformations of cyclohex-2-en-1-one cis-diol and hydroquinone metabolites, using Pseudomonas putida UV4 whole cells, were found to yield 4-hydroxycyclohex-2-en-1-ones as a new type of phenol bioproduct. Multistep pathways, involving ene reductase and carbonyl reductase-catalysed reactions, were proposed to account for the production of 4-hydroxycyclohex-2-en-1-one metabolites. Evidence for the phenol hydrate tautomers of 4-hydroxycyclohex-2-en-1-one metabolites was shown by formation of the corresponding trimethysilyl ether derivatives.
Original language | English |
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Pages (from-to) | 4002-4014 |
Number of pages | 13 |
Journal | Advanced Synthesis and Catalysis |
Volume | 359 |
Issue number | 22 |
Early online date | 16 Nov 2017 |
DOIs | |
Publication status | Published - 23 Nov 2017 |
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Dive into the research topics of 'Enzyme-Catalysed Synthesis of Cyclohex-2-en-1-one cis-Diols from Substituted Phenols, Anilines and Derived 4-Hydroxycyclohex-2-en-1-ones'. Together they form a unique fingerprint.Profiles
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Paul Stevenson
- School of Chemistry and Chemical Engineering - Emeritus Professor
- Organic Synthesis and Chemical Biology
Person: Emeritus, Academic