Visible-Light-Driven, Copper-Catalyzed Decarboxylative C(sp3)−H Alkylation of Glycine and Peptides
Chao Wang
Key Laboratory of Preclinical Study for New Drugs, of Gansu Province, School of Basic Medical Sciences, Lanzhou University, 199 West Donggang Road, Lanzhou, 730000 China
Search for more papers by this authorMengzhun Guo
Key Laboratory of Preclinical Study for New Drugs, of Gansu Province, School of Basic Medical Sciences, Lanzhou University, 199 West Donggang Road, Lanzhou, 730000 China
Search for more papers by this authorRupeng Qi
Key Laboratory of Preclinical Study for New Drugs, of Gansu Province, School of Basic Medical Sciences, Lanzhou University, 199 West Donggang Road, Lanzhou, 730000 China
Search for more papers by this authorQinyu Shang
Key Laboratory of Preclinical Study for New Drugs, of Gansu Province, School of Basic Medical Sciences, Lanzhou University, 199 West Donggang Road, Lanzhou, 730000 China
Search for more papers by this authorProf. Dr. Qiang Liu
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, 222 South Tianshui Road, Lanzhou, 730000 China
Search for more papers by this authorShan Wang
Key Laboratory of Preclinical Study for New Drugs, of Gansu Province, School of Basic Medical Sciences, Lanzhou University, 199 West Donggang Road, Lanzhou, 730000 China
Search for more papers by this authorLong Zhao
Key Laboratory of Preclinical Study for New Drugs, of Gansu Province, School of Basic Medical Sciences, Lanzhou University, 199 West Donggang Road, Lanzhou, 730000 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Rui Wang
Key Laboratory of Preclinical Study for New Drugs, of Gansu Province, School of Basic Medical Sciences, Lanzhou University, 199 West Donggang Road, Lanzhou, 730000 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Zhaoqing Xu
Key Laboratory of Preclinical Study for New Drugs, of Gansu Province, School of Basic Medical Sciences, Lanzhou University, 199 West Donggang Road, Lanzhou, 730000 China
Search for more papers by this authorChao Wang
Key Laboratory of Preclinical Study for New Drugs, of Gansu Province, School of Basic Medical Sciences, Lanzhou University, 199 West Donggang Road, Lanzhou, 730000 China
Search for more papers by this authorMengzhun Guo
Key Laboratory of Preclinical Study for New Drugs, of Gansu Province, School of Basic Medical Sciences, Lanzhou University, 199 West Donggang Road, Lanzhou, 730000 China
Search for more papers by this authorRupeng Qi
Key Laboratory of Preclinical Study for New Drugs, of Gansu Province, School of Basic Medical Sciences, Lanzhou University, 199 West Donggang Road, Lanzhou, 730000 China
Search for more papers by this authorQinyu Shang
Key Laboratory of Preclinical Study for New Drugs, of Gansu Province, School of Basic Medical Sciences, Lanzhou University, 199 West Donggang Road, Lanzhou, 730000 China
Search for more papers by this authorProf. Dr. Qiang Liu
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, 222 South Tianshui Road, Lanzhou, 730000 China
Search for more papers by this authorShan Wang
Key Laboratory of Preclinical Study for New Drugs, of Gansu Province, School of Basic Medical Sciences, Lanzhou University, 199 West Donggang Road, Lanzhou, 730000 China
Search for more papers by this authorLong Zhao
Key Laboratory of Preclinical Study for New Drugs, of Gansu Province, School of Basic Medical Sciences, Lanzhou University, 199 West Donggang Road, Lanzhou, 730000 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Rui Wang
Key Laboratory of Preclinical Study for New Drugs, of Gansu Province, School of Basic Medical Sciences, Lanzhou University, 199 West Donggang Road, Lanzhou, 730000 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Zhaoqing Xu
Key Laboratory of Preclinical Study for New Drugs, of Gansu Province, School of Basic Medical Sciences, Lanzhou University, 199 West Donggang Road, Lanzhou, 730000 China
Search for more papers by this authorGraphical Abstract
Out of the clear blue: The title reaction was developed for preparing α-alkylated non-natural α-amino acids by transformation of glycine moieties. Mild conditions and good functional-group tolerance allow the modification of peptides using this method. Mechanistic studies revealed that a radical–radical coupling pathway is involved in the reaction.
Abstract
Despite a well-developed and growing body of work in Cu catalysis, the potential of Cu to serve as a photocatalyst remains underexplored. Reported herein is the first example of visible-light-induced Cu-catalyzed decarboxylative C(sp3)−H alkylation of glycine for preparing α-alkylated unnatural α-amino acids. It merits mentioning that the mild conditions and the good functional-group tolerance allow the modification of peptides using this method. The mechanistic studies revealed that a radical–radical coupling pathway is involved in the reaction.
Supporting Information
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