Issue 22, 2021

Stereo-selective synthesis of non-canonical γ-hydroxy-α-amino acids by enzymatic carbon–carbon bond formation

Abstract

Carbon–carbon (C–C) bond formation is the fundamental reaction type in organic synthesis. Biocatalytic methods for C–C bond formation have been limited to a few types of enzymes. In this report, we demonstrated the capability of a PLP-dependent enzyme ApUstD performing both C–C bond activation and asymmetric C–C bond formation, which resulted in non-canonical γ-hydroxy-α-amino acids. The reaction showed high efficiency (conversion up to 98%), stereo-selectivity (ratio up to >97 : 3), a broad substrate scope (25 isolated examples) and significant simplicity. Our results have extended the biocatalytic function of PLP-dependent enzymes for asymmetric C–C formation.

Graphical abstract: Stereo-selective synthesis of non-canonical γ-hydroxy-α-amino acids by enzymatic carbon–carbon bond formation

Supplementary files

Article information

Article type
Paper
Submitted
28 May 2021
Accepted
03 Oct 2021
First published
04 Oct 2021

Catal. Sci. Technol., 2021,11, 7380-7385

Stereo-selective synthesis of non-canonical γ-hydroxy-α-amino acids by enzymatic carbon–carbon bond formation

R. Zhang, J. Tan, Z. Luo, H. Dong, N. Ma and C. Liao, Catal. Sci. Technol., 2021, 11, 7380 DOI: 10.1039/D1CY00955A

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