Copper-catalyzed asymmetric C(sp3)-H cyanoalkylation of glycine derivatives and peptides

Rupeng Qi, Qiao Chen, Liangyu Liu, Zijian Ma, Da Pan, Hongying Wang, Zhixuan Li, Chao Wang () and Zhaoqing Xu ()
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Rupeng Qi: School of Pharmacy, Lanzhou University
Qiao Chen: School of Pharmacy, Lanzhou University
Liangyu Liu: School of Basic Medical Sciences, Lanzhou University
Zijian Ma: School of Basic Medical Sciences, Lanzhou University
Da Pan: School of Pharmacy, Lanzhou University
Hongying Wang: School of Basic Medical Sciences, Lanzhou University
Zhixuan Li: School of Basic Medical Sciences, Lanzhou University
Chao Wang: Chinese Academy of Medical Sciences, 2019RU066
Zhaoqing Xu: Chinese Academy of Medical Sciences, 2019RU066

Nature Communications, 2023, vol. 14, issue 1, 1-9

Abstract: Abstract Alkylnitriles play important roles in many fields because of their unique electronic properties and structural characteristics. Incorporating cyanoalkyl with characteristic spectroscopy and reactivity properties into amino acids and peptides is of special interest for potential imaging and therapeutic purposes. Here, we report a copper-catalyzed asymmetric cyanoalkylation of C(sp3)-H. In the reactions, glycine derivatives can effectively couple with various cycloalkanone oxime esters with high enantioselectivities, and the reaction can be applied to the late-stage modification of peptides with good yields and excellent stereoselectivities, which is useful for modern peptide synthesis and drug discovery. The mechanistic studies show that the in situ formed copper complex by the coordination of glycine derivatives and chiral phosphine Cu catalyst can not only mediate the single electronic reduction of cycloalkanone oxime ester but also control the stereoselectivity of the cyanoalkylation reaction.

Date: 2023
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DOI: 10.1038/s41467-023-38871-1

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