期刊
CHEMISTRYSELECT
卷 7, 期 4, 页码 -出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/slct.202104090
关键词
Active pharmaceutical ingredients; Biocatalysis; Candida antarctica lipase B; Enzyme catalysis; Moxifloxacin
This work presents the enantioselective resolution of a water-soluble racemic mixture catalyzed by Candida antarctica lipase B, achieving both separation and efficient utilization of the products.
This work presents the enantioselective resolution of a water-soluble racemic mixture of cis-dimethyl 1-acetylpiperidine-2,3-dicarboxylate catalyzed by Candida antarctica lipase B. The separation of the carboxylic acid product in its (2R,3S) configuration from non-reacted substrate in the (2S,3R) configuration was easily obtained by organic phase extraction. The latter molecule can be used as an enantiomerically pure precursor in the synthesis of (4aS,7aS)-octahydro-1H-pyrrolo[3,4-b]pyridine, an expensive building block in the production of the antibiotic Moxifloxacin. On the other hand, the hydrolyzed product in the (2R,3S) configuration can be used for the preparation of a neuromediator analogue. The lipase demonstrated enantioselectivity towards the (2R,3S) substrate enantiomer and regioselectivity towards the ester in position 3 of the molecule. Studies of hydrolysis kinetics and the use of the immobilized enzyme were performed to evaluate its industrial application.
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