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Lipase-catalysed two-step desymmetrization of 2-methylmalonic dipyrazolide for preparation of optically pure enantiomer in organic solvents

Biocatalysis and Biotransformation, ISSN: 1029-2446, Vol: 35, Issue: 6, Page: 460-467
2017
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Article Description

A lipase-catalysed two-step butanolytic desymmetrization process for the preparation of pyrazolidyl butyl (S)-2-methylmalonate from 2-methylmalonic dipyrazolide was developed. The best reaction condition of using lipase PS-D in anhydrous n-hexane at 55 °C was first selected, leading to high yield and enantiomeric excess for the remained (S)-enantiomer. The kinetic analysis by considering the competitive inhibition from butanol was then carried out for obtaining the stereoselectivity of E = 11.2 for the first desymmetrization and enantiomeric ratio of EE=11.8 for the subsequent kinetic resolution. The thermodynamic analysis furthermore revealed that the enzyme stereodiscrimination was enthalpy-driven for the desymmetrization step, but changed as entropy-driven for the kinetic resolution step.

Bibliographic Details

Ching Hsiang Hsu; Shau Wei Tsai

Informa UK Limited

Biochemistry, Genetics and Molecular Biology; Chemical Engineering

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