The potential role of cis-dihydrodiol intermediates in bacterial aromatic hydroxylation and the NIH Shift
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 0300-922XFull text not available from this repository.
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|
|Date:||21 October 1998|
|Number of Pages:||9|
|Page Range:||pp. 3443-3451|
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