Trichosporon cutaneum-promoted deracemization of (+/-)-2-hydroxindan-l-one: a mechanistic study

dc.creatorCazetta, T
dc.creatorLunardi, I
dc.creatorConceicao, GJA
dc.creatorMorana, PJS
dc.creatorRodrigues, JAR
dc.date2007
dc.dateSEP 4
dc.date2014-11-14T10:16:59Z
dc.date2015-11-26T16:05:57Z
dc.date2014-11-14T10:16:59Z
dc.date2015-11-26T16:05:57Z
dc.date.accessioned2018-03-28T22:54:56Z
dc.date.available2018-03-28T22:54:56Z
dc.identifierTetrahedron-asymmetry. Pergamon-elsevier Science Ltd, v. 18, n. 17, n. 2030, n. 2036, 2007.
dc.identifier0957-4166
dc.identifierWOS:000250607100005
dc.identifier10.1016/j.tetasy.2007.08.007
dc.identifierhttp://www.repositorio.unicamp.br/jspui/handle/REPOSIP/76999
dc.identifierhttp://www.repositorio.unicamp.br/handle/REPOSIP/76999
dc.identifierhttp://repositorio.unicamp.br/jspui/handle/REPOSIP/76999
dc.identifier.urihttp://repositorioslatinoamericanos.uchile.cl/handle/2250/1265834
dc.descriptionA mechanistic study of the deracemization of (+/-)-2-hydroxy-l-indanone mediated by the yeast Trichosporon cutaneum to afford pure (1S,2R)-1,2-indandiol is reported. The key aspect of the study was the use of pure (R)- and (S)-2-hydroxy-l-indanone enantiomers to ensure reliable conclusions. Experiments in the absence of yeast cells or using dead cells disclosed that the pure enantiomers were not racemized, which suggest that the whole dynamic kinetic resolution process is enzymatic in character. When living yeast cells were used the (R)-substrate was smoothly converted to (1 S,2R)-1,2-indandiol, whilst the (S)-2-hydroxy-l-indanone was converted to the same diol through a more complex fashion, which requires a more lengthy oxidation-reduction pathway having the 1,2-indanedione as an achiral intermediate. An unexpected observation was that 1,2-indanone acts as a moderate inhibitor of the reductive enzymes acting in the conversion of (R)-2-hydroxy-l-indanone to (1S,2R)-1,2-indandiol. (C) 2007 Elsevier Ltd. All rights reserved.
dc.description18
dc.description17
dc.description2030
dc.description2036
dc.languageen
dc.publisherPergamon-elsevier Science Ltd
dc.publisherOxford
dc.publisherInglaterra
dc.relationTetrahedron-asymmetry
dc.relationTetrahedron: Asymmetry
dc.rightsfechado
dc.rightshttp://www.elsevier.com/about/open-access/open-access-policies/article-posting-policy
dc.sourceWeb of Science
dc.subjectDynamic Kinetic Resolution
dc.subjectBiocatalytic Racemization
dc.subjectAsymmetric-synthesis
dc.subjectCatalysis
dc.subjectCombination
dc.subjectOxidation
dc.subjectAlcohols
dc.subjectCells
dc.titleTrichosporon cutaneum-promoted deracemization of (+/-)-2-hydroxindan-l-one: a mechanistic study
dc.typeArtículos de revistas


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