Bioreduction Of Alpha-acetoxymethyl Enones: Proposal For An S(n)2 ' Mechanism Catalyzed By Enereductase

dc.creatorPaula
dc.creatorBruno R. S.; Zampieri
dc.creatorDavila; Rodrigues
dc.creatorJ. Augusto R.; Morana
dc.creatorPaulo J. S.
dc.date2016
dc.datenov
dc.date2017-11-13T13:23:11Z
dc.date2017-11-13T13:23:11Z
dc.date.accessioned2018-03-29T05:55:52Z
dc.date.available2018-03-29T05:55:52Z
dc.identifierAdvanced Synthesis & Catalysis. Wiley-v C H Verlag Gmbh, v. 358, p. 3555 - 3571, 2016.
dc.identifier1615-4150
dc.identifier1615-4169
dc.identifierWOS:000390408200008
dc.identifier10.1002/adsc.201600601
dc.identifierhttp://www.bv.fapesp.br/pt/publicacao/124618/bioreduction-of-alpha-acetoxymethyl-enones-proposal-for-an/
dc.identifierhttp://repositorio.unicamp.br/jspui/handle/REPOSIP/328048
dc.identifier.urihttp://repositorioslatinoamericanos.uchile.cl/handle/2250/1365073
dc.descriptionConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)
dc.descriptionFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
dc.description(Z)-3-Acetoxymethyl-4-R-3-buten-2-ones (R= aryl, alkyl) and (Z)-3-methyl-4-R-3-buten-2-ones (R= aryl) were synthesized and submitted to reduction by the yeast Saccharomyces cerevisiae producing the (R)-and (S)-4-R-3-methybutan-2-ones, respectively. This stereochemistry control strategy was applied in the syntheses of (R)-and (S)-Tropional U with moderate to high enantiomeric excesses. Other (Z)-3-acyloxymethyl-4-phenyl-3-buten-2-ones showed similar behavior to the (Z)-3-acetoxymethyl counterpart, and the acylated Morita-Baylis-Hillman adduct 1-acetoxy-2-methylene-1-phenylbutan-3-one produced a mixture of products, with and without the acetoxy group, via three different reaction path-ways. In addition to experiments employing whole cells, those in which isolated enereductases were used suggested that the main pathway through which the loss of the acetoxy group occurs during the biocatalytic cascade is an S(N)2'-type reaction, rather than formal hydrogen addition followed by acetic acid elimination. Finally, related ethyl enones were reduced enantioselectively by the yeast Candida albicans, producing both (R)-and (S)-reduction products, depending on the presence of the acetoxy group in the starting material.
dc.description358
dc.description22
dc.description3555
dc.description3571
dc.descriptionCNPq [304730/2013-0, 301811/2014-8, 143099/2006-0]
dc.descriptionFAPESP [2014/00108-9, 2012/08385-6]
dc.descriptionConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)
dc.descriptionFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
dc.languageEnglish
dc.publisherWiley-V C H Verlag Gmbh
dc.publisherWeinhem
dc.relationAdvanced Synthesis & Catalysis
dc.rightsfechado
dc.sourceWOS
dc.subjectBiotransformation
dc.subjectEnantioselectivity
dc.subjectEnones
dc.subjectEnzyme Catalysis
dc.titleBioreduction Of Alpha-acetoxymethyl Enones: Proposal For An S(n)2 ' Mechanism Catalyzed By Enereductase
dc.typeArtículos de revistas


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