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dc.creatorBoyd, Derek R.
dc.creatorSharma, Narain D.
dc.creatorMcMurray, Brian
dc.creatorHaughey, Simon A.
dc.creatorAllen, Christopher C. R.
dc.creatorHamilton, John T. G.
dc.creatorMcRoberts, W. Colin
dc.creatorO'Ferrall, Rory A. More
dc.creatorNikodinović-Runić, Jasmina
dc.creatorCoulombel, Lydie A.
dc.creatorO'Connor, Kevin E.
dc.date.accessioned2018-11-22T00:20:20Z
dc.date.available2018-11-22T00:20:20Z
dc.date.issued2012
dc.identifier.issn1477-0520
dc.identifier.urihttp://cherry.chem.bg.ac.rs/handle/123456789/1238
dc.description.abstractAsymmetric heteroatom oxidation of benzo[b]thiophenes to yield the corresponding sulfoxides was catalysed by toluene dioxygenase (TDO), naphthalene dioxygenase (NDO) and styrene monooxygenase (SMO) enzymes present in P. putida mutant and E. coli recombinant whole cells. TDO-catalysed oxidation yielded the relatively unstable benzo[b] thiophene sulfoxide; its dimerization, followed by dehydrogenation, resulted in the isolation of stable tetracyclic sulfoxides as minor products with cis-dihydrodiols being the dominant metabolites. SMO mainly catalysed the formation of enantioenriched benzo[b] thiophene sulfoxide and 2-methyl benzo[b] thiophene sulfoxides which racemized at ambient temperature. The barriers to pyramidal sulfur inversion of 2- and 3-methyl benzo[b] thiophene sulfoxide metabolites, obtained using TDO and NDO as biocatalysts, were found to be ca.: 25-27 kcal mol(-1). The absolute configurations of the benzo[b] thiophene sulfoxides were determined by ECD spectroscopy, X-ray crystallography and stereochemical correlation. A site-directed mutant E. coli strain containing an engineered form of NDO, was found to change the regioselectivity toward preferential oxidation of the thiophene ring rather than the benzene ring.en
dc.publisherRoyal Soc Chemistry, Cambridge
dc.rightsrestrictedAccess
dc.sourceOrganic and Biomolecular Chemistry
dc.titleBacterial dioxygenase- and monooxygenase-catalysed sulfoxidation of benzo[b]thiophenesen
dc.typearticle
dc.rights.licenseARR
dcterms.abstractО'Цоннор, Кевин Е.; Боyд, Дерек Р.; Цоуломбел, Лyдие A.; О'Ферралл, Рорy A. Море; МцРобертс, W. Цолин; Хамилтон, Јохн Т. Г.; Aллен, Цхристопхер Ц. Р.; Хаугхеy, Симон A.; Никодиновић-Рунић, Јасмина; МцМурраy, Бриан; Схарма, Нараин Д.;
dc.citation.volume10
dc.citation.issue4
dc.citation.spage782
dc.citation.epage790
dc.identifier.wos000298751900013
dc.identifier.doi10.1039/c1ob06678a
dc.citation.other10(4): 782-790
dc.citation.rankM21
dc.identifier.pmid22134441
dc.type.versionpublishedVersionen
dc.identifier.scopus2-s2.0-84555178925
dc.identifier.rcubKon_2260


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