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The potential role of cis-dihydrodiol intermediates in bacterial aromatic hydroxylation and the NIH Shift
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UNSPECIFIED (1998) The potential role of cis-dihydrodiol intermediates in bacterial aromatic hydroxylation and the NIH Shift. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 (20). pp. 3443-3451. ISSN 0300-922X
Full text not available from this repository.Abstract
Specifically deuteriated samples of toluene, anisole, chlorobenzene, alpha,alpha,alpha-trifluoromethylbenzene, naphthalene and quinoline have been synthesised and used as substrates for dioxygenase-catalysed asymmetric dihydroxylation studies to yield the corresponding cis-dihydrodiols as major bioproducts. Phenols were also detected as minor metabolites in some cases. Dehydration of the deuterium-labelled cis-dihydrodiol metabolites, under thermal conditions, in all cases, resulted in phenol formation accompanied by the NIH Shift. A comparison of NIH Shift results, obtained when phenols are produced by aromatisation of chemically synthesised deuteriated arene cis- and trans-dihydrodiols (dehydration) and arene oxides (isomerisation), suggests that this phenomenon may be associated with both monooxygenase- and dioxygenase-catalysed aromatic hydroxylations.
| Item Type: | Journal Article |
|---|---|
| Subjects: | Q Science > QD Chemistry |
| Journal or Publication Title: | JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 |
| Publisher: | ROYAL SOC CHEMISTRY |
| ISSN: | 0300-922X |
| Date: | 21 October 1998 |
| Number: | 20 |
| Number of Pages: | 9 |
| Page Range: | pp. 3443-3451 |
| Publication Status: | Published |
| URI: | http://wrap.warwick.ac.uk/id/eprint/15240 |
Data sourced from Thomson Reuters' Web of Knowledge
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