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

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Abstract

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

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Acknowledgments

GDY received support from R.T. Mody Distinguished Professor Endowment and J.C. Bose National Fellowship of Department of Science and Technology, Government of India. SVP thanks the University Grant Commission for an award of SRF.

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  1. Department of Chemical Engineering, Institute of Chemical Technology, Matunga, Mumbai, 400 019, India

    Ganapati D. Yadav & Sandip V. Pawar

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  1. Ganapati D. Yadav
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  2. Sandip V. Pawar
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Correspondence to Ganapati D. Yadav.

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Yadav, G.D., Pawar, S.V. Insight into microwave irradiation and enzyme catalysis in enantioselective resolution of dl-(±)-3-phenyllactic acid. Appl Microbiol Biotechnol 96, 69–79 (2012). https://doi.org/10.1007/s00253-012-4183-0

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