A study on the enzyme catalysed enantioselective hydrolysis of methyl 2-methyl-4-oxopentanoate, a precursor of chiral γ-butyrolactones

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dc.contributor.authorFerreira E.A.
dc.contributor.authorRodezno S.V.A.
dc.contributor.authorOmori A.T.
dc.contributor.authorCunha R.L.O.R.
dc.date.accessioned2024-03-12T23:53:40Z
dc.date.available2024-03-12T23:53:40Z
dc.date.issued2019
dc.description.abstract© 2018, © 2018 Informa UK Limited, trading as Taylor & Francis Group. Porcine pancreas lipase (PPL) resolution of the α-methyl group of racemic methyl 2-methyl-4-oxopentanoate, a valuable synthetic precursor of fragrances and marine natural products, was enhanced by salt modulation of the enzymatic hydrolysis. For the enantioselective hydrolysis of the title ester, PPL was selected from a series of esterases and lipases, and its enantioselectivity was evaluated by changing the reaction medium parameters. The use of 1.6 mol L –1 sodium sulfate in phosphate buffer (pH 7.2) improved the enantioselectivity allowing the formation of methyl (2R)-(+)-2-methyl-4-oxopentanoate and (2S)-(–)-2-methyl-4-oxopentanoic acid with an enantiomeric excess of >99% and 71%, respectively. The study showed that a modulation of PPL enantioselectivity could be achieved by using kosmotropic salts in the reaction media. The present method consists of a practical and low-cost option to improve enzymatic kinetic resolution reactions.
dc.description.firstpage115
dc.description.issuenumber2
dc.description.lastpage123
dc.description.volume37
dc.identifier.doi10.1080/10242422.2018.1502274
dc.identifier.issn1029-2446
dc.identifier.urihttps://dspace.mackenzie.br/handle/10899/35295
dc.relation.ispartofBiocatalysis and Biotransformation
dc.rightsAcesso Restrito
dc.subject.otherlanguageEnzymatic kinetic resolution
dc.subject.otherlanguageHofmeister effect
dc.subject.otherlanguageinterfacial enzymes
dc.subject.otherlanguagemedium engineering
dc.subject.otherlanguagesalting-out
dc.titleA study on the enzyme catalysed enantioselective hydrolysis of methyl 2-methyl-4-oxopentanoate, a precursor of chiral γ-butyrolactones
dc.typeArtigo
local.scopus.citations4
local.scopus.eid2-s2.0-85057320581
local.scopus.subjectEnantiomeric excess
local.scopus.subjectEnantioselective hydrolysis
local.scopus.subjectEnzymatic kinetic resolutions
local.scopus.subjectHofmeister effects
local.scopus.subjectMarine natural products
local.scopus.subjectPorcine pancreas lipase
local.scopus.subjectSalting out
local.scopus.subjectSynthetic precursors
local.scopus.updated2024-05-01
local.scopus.urlhttps://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85057320581&origin=inward
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