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Dioxygenase-catalysed oxidation of disubstituted benzene substrates : benzylic monohydroxylation versus aryl cis-dihydroxylation and the meta effect
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Boyd, Derek R., Sharma, Narain D., Bowers, Nigel I., Dalton, Howard, Garrett, Mark D., Harrison, John S. and Sheldrake, Gary N. (2006) Dioxygenase-catalysed oxidation of disubstituted benzene substrates : benzylic monohydroxylation versus aryl cis-dihydroxylation and the meta effect. Organic & Biomolecular Chemistry, Volume 4 (Number 17). pp. 3343-3349. doi:10.1039/b608417f ISSN 1477-0520.
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Official URL: http://dx.doi.org/10.1039/b608417f
Abstract
Biotransformations of a series of ortho-, meta- and para-substituted ethylbenzene and propylbenzene substrates have been carried out, using Pseudomonas putida UV4, a source of toluene dioxygenase (TDO). The ortho- and para-substituted alkylbenzene substrates yielded, exclusively, the corresponding enantiopure cis-dihydrodiols of the same absolute configuration. However, the meta isomers, generally, gave benzylic alcohol bioproducts, in addition to the cis-dihydrodiols ( the meta effect). The benzylic alcohols were of identical ( R) absolute configuration but enantiomeric excess values were variable. The similar (2R) absolute configurations of the cis-dihydrodiols are consistent with both the ethyl and propyl groups having dominant stereodirecting effects over the other substituents. The model used earlier, to predict the regio- and stereo-chemistry of cis-dihydrodiol bioproducts derived from substituted benzene substrates has been refined, to take account of non-symmetric subsituents like ethyl or propyl groups. The formation of benzylic hydroxylation products, from meta- substituted benzene substrates, without further cis-dihydroxylation to yield triols provides a further example of the meta effect during toluene dioxygenase-catalysed oxidations.
Item Type: | Journal Article | ||||
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Subjects: | Q Science > QD Chemistry | ||||
Divisions: | Faculty of Science, Engineering and Medicine > Science > Life Sciences (2010- ) > Biological Sciences ( -2010) | ||||
Journal or Publication Title: | Organic & Biomolecular Chemistry | ||||
Publisher: | Royal Society of Chemistry | ||||
ISSN: | 1477-0520 | ||||
Official Date: | 2006 | ||||
Dates: |
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Volume: | Volume 4 | ||||
Number: | Number 17 | ||||
Number of Pages: | 7 | ||||
Page Range: | pp. 3343-3349 | ||||
DOI: | 10.1039/b608417f | ||||
Status: | Peer Reviewed | ||||
Publication Status: | Published | ||||
Access rights to Published version: | Restricted or Subscription Access |
Data sourced from Thomson Reuters' Web of Knowledge
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