Enantioselective biocatalytic desymmetrization for synthesis of enantiopure cis-3,4-disubstituted pyrrolidines

Autor: Hui-Juan Hu, Qi-Qiang Wang, De-Xian Wang, Yu-Fei Ao
Jazyk: angličtina
Rok vydání: 2021
Předmět:
Zdroj: Green Synthesis and Catalysis, Vol 2, Iss 3, Pp 324-327 (2021)
Druh dokumentu: article
ISSN: 2666-5549
DOI: 10.1016/j.gresc.2021.07.002
Popis: A versatile biocatalytic desymmetric method for efficiently accessing enantiopure cis-3,4-disubstituted pyrrolidines was developed. Catalyzed by amidase-containing E. coli whole cells, a series of meso pyrrolidine-2,5-dicarboxamides were hydrolyzed to obtain 4-carbamoylpyrrolidine-3-carboxylic acid derivatives in 47%–95% yields and 62% ∼ >99.5% ee values under mild condition. The catalytic efficiency and enantioselectivity are related to the substituents in the phenyl ring. The enzyme-substrate binding mode is established and the high enantioselectivity of amidase is revealed by MD simulations. The improvement of biocatalytic efficiency has been preliminarily explored through protein engineering.
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