Asymmetric assembly of high-value α-functionalized organic acids using a biocatalytic chiral-group-resetting process

Wei Song, Jin-Hui Wang, Jing Wu, Jia Liu, Xiu-Lai Chen and Li-Ming Liu ()
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Wei Song: Jiangnan University
Jin-Hui Wang: Jiangnan University
Jing Wu: Jiangnan University
Jia Liu: Jiangnan University
Xiu-Lai Chen: Jiangnan University
Li-Ming Liu: Jiangnan University

Nature Communications, 2018, vol. 9, issue 1, 1-9

Abstract: Abstract The preparation of α-functionalized organic acids can be greatly simplified by adopting a protocol involving the catalytic assembly of achiral building blocks. However, the enzymatic assembly of small amino acids and aldehydes to form numerous α-functionalized organic acids is highly desired and remains a significant challenge. Herein, we report an artificially designed chiral-group-resetting biocatalytic process, which uses simple achiral glycine and aldehydes to synthesize stereodefined α-functionalized organic acids. This cascade biocatalysis comprises a basic module and three different extender modules and operates in a modular assembly manner. The engineered Escherichia coli catalysts, which contained different module(s), provide access to α-keto acids, α-hydroxy acids, and α-amino acids with excellent conversion and enantioselectivities. Therefore, this biocatalytic process provides an attractive strategy for the conversion of low-cost achiral starting materials to high-value α-functionalized organic acids.

Date: 2018
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DOI: 10.1038/s41467-018-06241-x

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