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...
Published in: | ASEAN Journal of Chemical Engineering |
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Online Access: | http://eprints.ums.edu.my/id/eprint/25974/ http://eprints.ums.edu.my/id/eprint/25974/1/Effect%20of%20Reaction%20Parameters%20on%20the%20Lipase-Catalyzed%20Kinetic%20Resolution%20of%20%28RS%29-Metoprolol.pdf http://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://doi.org/10.22146/ajche.51857 |
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ftunivmalaysab:oai:eprints.ums.edu.my:25974 2023-05-15T13:35:53+02:00 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 2020 text http://eprints.ums.edu.my/id/eprint/25974/ http://eprints.ums.edu.my/id/eprint/25974/1/Effect%20of%20Reaction%20Parameters%20on%20the%20Lipase-Catalyzed%20Kinetic%20Resolution%20of%20%28RS%29-Metoprolol.pdf http://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://doi.org/10.22146/ajche.51857 en eng http://eprints.ums.edu.my/id/eprint/25974/1/Effect%20of%20Reaction%20Parameters%20on%20the%20Lipase-Catalyzed%20Kinetic%20Resolution%20of%20%28RS%29-Metoprolol.pdf http://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. T Technology (General) TA Engineering (General). Civil engineering (General) Article PeerReviewed 2020 ftunivmalaysab https://doi.org/10.22146/ajche.51857 2022-03-29T15:41:39Z 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. Article in Journal/Newspaper Antarc* Antarctica Universiti Malaysia Sabah: UMS Institutional Repository ASEAN Journal of Chemical Engineering 20 1 20 |
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Open Polar |
collection |
Universiti Malaysia Sabah: UMS Institutional Repository |
op_collection_id |
ftunivmalaysab |
language |
English |
topic |
T Technology (General) TA Engineering (General). Civil engineering (General) |
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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 |
topic_facet |
T Technology (General) TA Engineering (General). Civil engineering (General) |
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. |
format |
Article in Journal/Newspaper |
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 |
title |
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_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_sort |
effect of reaction parameters on the lipase-catalyzed kinetic resolution of (rs)-metoprolol |
publishDate |
2020 |
url |
http://eprints.ums.edu.my/id/eprint/25974/ http://eprints.ums.edu.my/id/eprint/25974/1/Effect%20of%20Reaction%20Parameters%20on%20the%20Lipase-Catalyzed%20Kinetic%20Resolution%20of%20%28RS%29-Metoprolol.pdf http://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://doi.org/10.22146/ajche.51857 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_relation |
http://eprints.ums.edu.my/id/eprint/25974/1/Effect%20of%20Reaction%20Parameters%20on%20the%20Lipase-Catalyzed%20Kinetic%20Resolution%20of%20%28RS%29-Metoprolol.pdf http://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. |
op_doi |
https://doi.org/10.22146/ajche.51857 |
container_title |
ASEAN Journal of Chemical Engineering |
container_volume |
20 |
container_issue |
1 |
container_start_page |
20 |
_version_ |
1766071562398597120 |