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Stereochemical and mechanistic aspects of dioxygenase-catalysed benzylic hydroxylation of indene and chromane substrates
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UNSPECIFIED. (2003) Stereochemical and mechanistic aspects of dioxygenase-catalysed benzylic hydroxylation of indene and chromane substrates. ORGANIC & BIOMOLECULAR CHEMISTRY, 1 (8). pp. 1298-1307. ISSN 1477-0520
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Official URL: http://dx.doi.org/10.1039/b300898c
Abstract
Toluene dioxygenase (TDO)-catalysed benzylic hydroxylation of indene substrates (8, 16 and 17), using whole cell cultures of Pseudomonas putida UV4, was found to yield inden-1-ol (14 and 22) and indan-1-one bioproducts (15 and 23). The formation of these bioproducts is consistent with the involvement of carbon-centred radical intermediates. TDO-catalysed oxidation of indenes 8 and 16 also gave cis-diols 13 and 18 respectively. TDO and naphthalene dioxygenase (NDO), used as both whole-cell preparations and as purified enzymes, were found to catalyse the benzylic hydroxylation of chromane 30, deuteriated (+/-)-chromane 30(D) and enantiomers (4S)-30(D) and (4R)-30(D) to yield (4R)- and (4S)-chroman-4-ols 31/31(D) respectively. The mechanism of benzylic hydroxylation of chromane 30/30(D) involves the stereoselective abstraction of a pro-R (with TDO) or a pro-S (with NDO) hydrogen atom at C-4 and a marked preference for retention of configuration.
| Item Type: | Journal Article |
|---|---|
| Subjects: | Q Science > QD Chemistry |
| Journal or Publication Title: | ORGANIC & BIOMOLECULAR CHEMISTRY |
| Publisher: | ROYAL SOC CHEMISTRY |
| ISSN: | 1477-0520 |
| Date: | 2003 |
| Volume: | 1 |
| Number: | 8 |
| Number of Pages: | 10 |
| Page Range: | pp. 1298-1307 |
| Identification Number: | 10.1039/b300898c |
| Publication Status: | Published |
| URI: | http://wrap.warwick.ac.uk/id/eprint/9812 |
Data sourced from Thomson Reuters' Web of Knowledge
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