Asymmetric biomimetic transamination of α-keto amides to peptides

Weiqi Cai, Xuelong Qiao, Hao Zhang, Bo Li, Jianhua Guo, Liangliang Zhang, Wen-Wen Chen and Baoguo Zhao ()
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Weiqi Cai: Shanghai Normal University
Xuelong Qiao: Shanghai Normal University
Hao Zhang: Shanghai Normal University
Bo Li: Shanghai Normal University
Jianhua Guo: Shanghai Normal University
Liangliang Zhang: Shanghai Normal University
Wen-Wen Chen: Shanghai Normal University
Baoguo Zhao: Shanghai Normal University

Nature Communications, 2021, vol. 12, issue 1, 1-9

Abstract: Abstract Peptides are important compounds with broad applications in many areas. Asymmetric transamination of α-keto amides can provide an efficient strategy to synthesize peptides, however, the process has not been well developed yet and still remains a great challenge in both enzymatic and catalytic chemistry. For biological transamination, the high activity is attributed to manifold structural and electronic factors of transaminases. Based on the concept of multiple imitation of transaminases, here we report N-quaternized axially chiral pyridoxamines 1 for enantioselective transamination of α-keto amides, to produce various peptides in good yields with excellent enantio- and diastereoselectivities. The reaction is especially attractive for the synthesis of peptides made of unnatural amino acids since it doesn’t need great efforts to make chiral unnatural amino acids before amide bond formation.

Date: 2021
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DOI: 10.1038/s41467-021-25449-y

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