Insight into microwave irradiation and enzyme catalysis in enantioselective resolution of dl -(±)-3-phenyllactic acid

作者: Ganapati D. Yadav , Sandip V. Pawar

DOI: 10.1007/S00253-012-4183-0

关键词: Enzyme catalysisCatalysisLipaseOrganic chemistryEnantioselective synthesisChemistryVinyl acetateEnantiomeric excessTransesterificationKinetic resolutionNuclear chemistry

摘要: Lipase catalyzed kinetic resolution of dl-(±)-3-phenyllactic acid (dl-(±)-3-PLA) was investigated to study the synergistic effect microwave irradiation and enzyme catalysis. Lipases from different sources were employed for transesterification dl-(±)-3-PLA under otherwise similar conditions, among which Novozyme 435 efficiently l-(−)-O-acetyl-3-PLA using vinyl acetate as acyl donor, showing excellent conversion (49 %) enantiomeric excess (>99 %). The various parameters affecting initial rate, reaction studied establish kinetics mechanism. There is a synergism between catalysis irradiation; an increase in rates up 1.8-fold observed than that conventional heating. analysis rate data showed obeys ternary complex (ordered bi-bi) mechanism with inhibition by dl-(±)-3-PLA. calculated simulated match very well validity proposed model.

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