Coupled Immobilized Amine Dehydrogenase and Glucose Dehydrogenase for Asymmetric Synthesis of Amines by Reductive Amination with Cofactor Recycling. Issue 3 (18th January 2017)

• Record Type: Journal Article
• Authors: Liu, Ji; Pang, Bryan Q. W.; Adams, Joseph P.; Snajdrova, Radka; Li, Zhi
• Is Part Of: ChemCatChem. Volume 9:Issue 3(2017)
• Page Start: 425
• Page End: 431
• Publication Date: 2017-01-18
• Subjects: biocatalysis -- biotransformations -- enantioselectivity -- enzyme immobilization; Catalysis -- Periodicals; 541.39505
• DOI: 10.1002/cctc.201601446
• Languages: English
• ISSNs: 1867-3880

Abstract

Abstract: The amine dehydrogenase (AmDH) engineered from the phenylalanine dehydrogenase of Rhodococcus sp. M4 was directly immobilized on magnetic nanoparticles (MNP) from the cell‐free extract containing his‐tagged AmDH through affinity attachment to give AmDH‐MNPs with high yield, enzyme loading efficiency, and specific enzyme loading. AmDH‐MNPs showed higher activity and productivity than the free enzyme for the asymmetric reductive amination of 4‐phenyl‐2‐butanone1 a and phenylacetone1 b, producing the corresponding amines ( R )‐2 a, b in 99 % ee and 99 % yield, and with recycling of NADH for up to 3956 times. AmDH‐MNPs were easily recycled, retaining 91 % of the original productivity in the third cycle of the reductive amination of1 a . Coupling of immobilized AmDH and immobilized glucose dehydrogenase (GDH) for the asymmetric reductive amination of1 a gave ( R )‐2 a in 99 % ee and 74 % yield, with a total turnover number (TTN) of 2940 for NADH recycling. Both immobilized enzymes showed good recyclability, retaining 81 % productivity in the third reaction cycle. The developed method with coupled immobilized AmDH and immobilized GDH for the asymmetric reductive amination of ketones is useful for the synthesis of enantiopure amines, superior to the use of coupled isolated enzymes with enhanced catalytic performance and reduced enzyme cost through catalyst recycling. Abstract : Tied together : A new concept of using coupled immobilized enzymes for efficient reductive amination of ketones to produce enantiopure amines is successfully demonstrated.