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...
| Principais autores: | , , , , |
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| Formato: | Artigo |
| Idioma: | English English |
| Publicado em: |
2020
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| Assuntos: | |
| Acesso em linha: | 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 |
| _version_ | 1825713953799405568 |
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| author | Mariani Rajin Asiah Zulkifli Sariah Abang S.M Anissuzzaman Azlina Harun Kamaruddin |
| author_facet | Mariani Rajin Asiah Zulkifli Sariah Abang S.M Anissuzzaman Azlina Harun Kamaruddin |
| author_sort | Mariani Rajin |
| collection | UMS |
| description | 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. |
| first_indexed | 2024-03-06T03:04:34Z |
| format | Article |
| id | ums.eprints-25974 |
| institution | Universiti Malaysia Sabah |
| language | English English |
| last_indexed | 2024-03-06T03:04:34Z |
| publishDate | 2020 |
| record_format | dspace |
| spelling | ums.eprints-259742021-04-09T09:10:15Z https://eprints.ums.edu.my/id/eprint/25974/ Effect of Reaction Parameters on the Lipase-Catalyzed Kinetic Resolution of (RS)-Metoprolol Mariani Rajin Asiah Zulkifli Sariah Abang S.M Anissuzzaman Azlina Harun Kamaruddin T Technology (General) TA Engineering (General). Civil engineering (General) 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. 2020 Article PeerReviewed text en 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 text en 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 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. https://doi.org/10.22146/ajche.51857 |
| spellingShingle | T Technology (General) TA Engineering (General). Civil engineering (General) Mariani Rajin Asiah Zulkifli Sariah Abang S.M Anissuzzaman Azlina Harun Kamaruddin Effect of Reaction Parameters on the Lipase-Catalyzed Kinetic Resolution of (RS)-Metoprolol |
| title | Effect of Reaction Parameters on the Lipase-Catalyzed Kinetic Resolution of (RS)-Metoprolol |
| title_full | Effect of Reaction Parameters on the Lipase-Catalyzed Kinetic Resolution of (RS)-Metoprolol |
| title_fullStr | Effect of Reaction Parameters on the Lipase-Catalyzed Kinetic Resolution of (RS)-Metoprolol |
| title_full_unstemmed | Effect of Reaction Parameters on the Lipase-Catalyzed Kinetic Resolution of (RS)-Metoprolol |
| title_short | Effect of Reaction Parameters on the Lipase-Catalyzed Kinetic Resolution of (RS)-Metoprolol |
| title_sort | effect of reaction parameters on the lipase catalyzed kinetic resolution of rs metoprolol |
| topic | T Technology (General) TA Engineering (General). Civil engineering (General) |
| url | 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 |
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