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Lipase-catalyzed asymmetric hydrolysis of 3-phenylglycidic acid ester, the key intermediate in the synthesis of diltiazem hydrochloride

, : Lipase-catalyzed asymmetric hydrolysis of 3-phenylglycidic acid ester, the key intermediate in the synthesis of diltiazem hydrochloride. Journal Of Fermentation & Bioengineering. 75(2): 93-98

Asymmetric hydrolytic enzymes for trans-3-(4-methoxyphenyl)glycidic acid methyl ester ((+-)-MPGM), a key intermediate in the synthesis of diltiazem hydrochloride that is useful as a coronary vasodilator, were screened from 730 microorganisms. Among the microbial enzymes tested, Serratia marcescens lipase had the highest enantioselectivity (E = 135) for hydrolysis of (+-)-MPGM in a two-phase system using water (pH 8) and a water-immiscible solvent such as toluene. Resolution of (+-)-MPGM by S. marcescens lipase gave (2R, 3S)-3-(4-methoxyphenyl)glycidic acid methyl ester ((-)-MPGM) with a reaction yield of 48% and optical purity of gt 99.9% e.e. After the reaction, the emulsion of toluene and water was separated into two clear layers by the addition of sodium dodecyl sulfate. The crystalline ( sbd )-MPGM was isolated with a yield of over 43% and optical purity of 100% e.e. without column treatment. Diltiazem hydrochloride synthesis using asymmetric hydrolysis of (+-)-MPGM was found to be a more efficient process compared to the conventional chemical synthetic process. Some enzymatic characterizations on asymmetric in two-phases of organic solvent-water by S. marcescens lipase were investigated.


DOI: 10.1016/0922-338x(93)90216-u

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