Effect of Reaction Parameters on the Lipase-Catalyzed Kinetic Resolution of (RS)-Metoprolol
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 incr...
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| Main Authors: | , , , , |
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| Format: | Article |
| Language: | en en |
| Published: |
2020
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| Subjects: | |
| Online Access: | https://eprints.ums.edu.my/id/eprint/25974/1/Effect%20of%20Reaction%20Parameters%20on%20the%20Lipase-Catalyzed%20Kinetic%20Resolution%20of%20%28RS%29-Metoprolol.pdf https://eprints.ums.edu.my/id/eprint/25974/2/Effect%20of%20Reaction%20Parameters%20on%20the%20Lipase-Catalyzed%20Kinetic%20Resolution%20of%20%28RS%29-Metoprolol1.pdf https://eprints.ums.edu.my/id/eprint/25974/ https://doi.org/10.22146/ajche.51857 |
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| Summary: | 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. |
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