反应参数对脂肪酶催化(RS)-美托洛尔动力学拆分的影响

Q4 Chemical Engineering ASEAN Journal of Chemical Engineering Pub Date : 2020-06-29 DOI:10.22146/ajche.51857
M. Rajin, Asiah binti Zulkifli, S. Abang, S. Anissuzzaman, A. Kamaruddin
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引用次数: 0

摘要

外消旋美托洛尔是一种选择性ß1受体阻滞剂,用于心血管疾病的治疗。研究发现(S)-美托洛尔与(R)-美托洛尔相比,对ß-肾上腺素能受体具有更高的亲和力。此外,监管部门的高市场需求和指导方针增加了对单一对映体药物的偏好。在这项工作中,脂肪酶催化的外消旋美托洛尔动力学拆分得到所需的对映体。筛选了脂肪酶类型、酰基供体和溶剂。利用南极念珠菌B脂酶催化外消旋美托洛尔在己烷和乙酸乙烯基为溶剂和酰基供体的条件下进行酯交换反应,得到(S)-美托洛尔(XS)的最大转化率为52%,底物对映体过量(ees)为92%,产物(eeP)为90%,对映体比(E)为62。该方法可视为绿色化学,可用于生产其他对映不纯β受体阻滞剂。
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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 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 lipase-catalyzed 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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ASEAN Journal of Chemical Engineering
ASEAN Journal of Chemical Engineering Chemical Engineering-Chemical Engineering (all)
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