Effect of Reaction Parameters on the Lipase-Catalyzed Kinetic Resolution of (RS)-Metoprolol

Mariani Rajin and Asiah Zulkifli and Sariah Abang and S.M Anissuzzaman and Azlina Harun Kamaruddin (2020) Effect of Reaction Parameters on the Lipase-Catalyzed Kinetic Resolution of (RS)-Metoprolol. AJChE, 20 (1). pp. 20-30.

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Abstract

Racemic metoprolol is a selective ß1-blocker, which is used in cardiovascular disease treatment. It has been found that (S)-metoprolol has a higher affinity to bind the ß-adrenergic receptor compared to (R)-metoprolol. Moreover, the regulatory authorities’ high market demand and guidelines have increased the preference for single enantiomer drugs. In this work, the lipase-catalyzed kinetic resolution of racemic metoprolol was performed to obtain the desired enantiomer. The type of lipase, acyl donor, and solvent were screened out. This was achieved by Candida antarctica B lipasecatalyzed transesterification of racemic metoprolol in hexane and vinyl acetate as the solvent and an acyl donor, which gave maximum conversion of (S)-metoprolol (XS) of 52%, enantiomeric excess of substrate, (ees) of 92% and product (eeP) of 90% with enantiomeric ratio (E) of 62. This method can be considered as green chemistry, which can be applied to produce other enantiopure beta-blockers.

Item Type:	Article
Keyword:	Beta-blocker, Chiral drug, Metoprolol, Kinetic resolution, Lipase
Subjects:	T Technology > T Technology (General) T Technology > TA Engineering (General). Civil engineering (General)
Department:	FACULTY > Faculty of Engineering
Depositing User:	SITI AZIZAH BINTI IDRIS -
Date Deposited:	21 Sep 2020 08:19
Last Modified:	09 Apr 2021 17:10
URI:	https://eprints.ums.edu.my/id/eprint/25974

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