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

ABSTRACT: The preparation of ?-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 ?-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 ?-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 ?-keto acids, ?-hydroxy acids, and ?-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 ?-functionalized organic acids.

SUBMITTER: Song W 

PROVIDER: S-EPMC6145935 | biostudies-literature | 2018 Sep

REPOSITORIES: biostudies-literature