Abstract
Biocatalytic transamination is widely used in industrial production of chiral chemicals. Here, we constructed a novel multi-enzyme system to promote the conversion of the amination reaction. Firstly, we constructed the ArR-ωTA/TdcE/FDH/LDH multi-enzyme system, by combination of (R)-selective ω-transaminase derived from Arthrobacter sp. (ArR-ωTA), formate dehydrogenase (FDH) derived from Candida boidinii, formate acetyltransferase (TdcE) and lactate dehydrogenase (LDH) derived from E. coli MG1655. This multi-enzyme system was used to efficiently remove the by-product pyruvate by TdcE and LDH to facilitate the transamination reaction. The TdcE/FDH pathway was found to dominate the by-product pyruvate removal in the transamination reaction. Secondly, we optimized the reaction conditions, including d-alanine, DMSO, and pyridoxal phosphate (PLP) with different concentration of 2-pentanone (as a model substrate). Thirdly, by using the ArR-ωTA/TdcE/FDH/LDH system, the conversions of 2-pentanone, 4-phenyl-2-butanone and cyclohexanone were 84.5%, 98.2% and 79.3%, respectively.
Highlights
Chiral amines are a class of compounds containing amino groups in the chiral center of small molecule compounds
We constructed the ArR-uTA/TdcE/FDH/LDH multi-enzyme system, by combination of (R)-selective u-transaminase derived from Arthrobacter sp. (ArR-uTA), formate dehydrogenase (FDH) derived from Candida boidinii, formate acetyltransferase (TdcE) and lactate dehydrogenase (LDH) derived from E. coli MG1655
We investigated the effects of D-alanine, DMSO, substrate concentration and pyridoxal phosphate (PLP) on the conversion of ketones to amines. 2-Pentanone was used as a model substrate in the optimization of reaction conditions
Summary
Chiral amines are a class of compounds containing amino groups in the chiral center of small molecule compounds. They are widely used in pharmaceutical and agricultural elds, such as neurological, cardiovascular, antihypertensive, anti-infective drugs, and vaccines, which play an important role in the national economy.[1,2,3,4,5] At present, the main methods for the preparation of chiral amines[6,7,8,9] are chemical synthesis, biological resolution and biological asymmetric synthesis. Biological asymmetric synthesis method becomes the preferred strategy for the production of chiral amines because of its theoretical conversion of up to 100%.16–19 the synthesis of chiral amines by biological asymmetric synthesis has been of increasing interest
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