Stereoselective Oxidation of 1-Phenyl-1,2-propanediol Mediated by Microorganisms

dc.creatorMartins, RS
dc.creatorZampieri, DS
dc.creatorRodrigues, JAR
dc.creatorCarvalho, PO
dc.creatorMoran, PJS
dc.date2011
dc.dateSEP
dc.date2014-07-31T14:14:09Z
dc.date2015-11-26T18:06:16Z
dc.date2014-07-31T14:14:09Z
dc.date2015-11-26T18:06:16Z
dc.date.accessioned2018-03-29T00:48:29Z
dc.date.available2018-03-29T00:48:29Z
dc.identifierChemcatchem. Wiley-blackwell, v. 3, n. 9, n. 1469, n. 1473, 2011.
dc.identifier1867-3880
dc.identifierWOS:000295228400015
dc.identifier10.1002/cctc.201100145
dc.identifierhttp://www.repositorio.unicamp.br/jspui/handle/REPOSIP/75214
dc.identifierhttp://repositorio.unicamp.br/jspui/handle/REPOSIP/75214
dc.identifier.urihttp://repositorioslatinoamericanos.uchile.cl/handle/2250/1293320
dc.descriptionFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
dc.descriptionConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)
dc.descriptionThe enantioselective oxidation of (1R,2S)-1-phenyl-1,2-propanediol [(1R,2S)-1], mediated by baker's yeast, gave (-)-(S)- 1-phenyl-2-hydroxy-1-propanone [(S)- 2] in 64% isolated yield and 93% ee. Kinetic experiments of the bio-oxidation of (+/-)-anti-1 revealed that the enantiomer (1R,2S)-1 was more reactive than (1S,2R)-1. Therefore, this result allowed us to devise a kinetic resolution experiment to obtain (1S,2R)-1 in > 99% ee from (+/-)-anti-1. The preparation of (1S,2R)-1 is interesting, as it is the antipode of the product obtained by the reduction of 1-phenyl-1,2-propanedione using baker's yeast. Other microorganisms, such as Micrococcus luteus, Candida albicans, and Geotrichum candidum, were also used for kinetic resolution experiments of (+/-)-anti-1. The best result was obtained using Geotrichum candidum, which gave (1S,2R)-1 in 32% yield and 99% ee.
dc.description3
dc.description9
dc.description1469
dc.description1473
dc.descriptionFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
dc.descriptionConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)
dc.descriptionFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
dc.descriptionConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)
dc.descriptionFAPESP [03/05882-0]
dc.languageen
dc.publisherWiley-blackwell
dc.publisherMalden
dc.publisherEUA
dc.relationChemcatchem
dc.relationChemCatChem
dc.rightsfechado
dc.rightshttp://olabout.wiley.com/WileyCDA/Section/id-406071.html
dc.sourceWeb of Science
dc.subjectalcohols
dc.subjectbiocatalysis
dc.subjectenantioselectivity
dc.subjectenzymes
dc.subjectkinetic resolution
dc.subjectParapsilosis Catalyzing Deracemization
dc.subjectBakers-yeast
dc.subjectBiocatalytic Oxidation
dc.subjectAsymmetric Reduction
dc.subjectMicrobial Oxidation
dc.subjectKinetic Resolution
dc.subjectSecondary Alcohols
dc.subjectCarbonyl-compounds
dc.subjectSec-alcohols
dc.subjectVic-diols
dc.titleStereoselective Oxidation of 1-Phenyl-1,2-propanediol Mediated by Microorganisms
dc.typeArtículos de revistas


Este ítem pertenece a la siguiente institución