Generation of Glycosyl Radicals from Glycosyl Sulfoxides and Its Use in the Synthesis of C-linked Glycoconjugates
Weidong Shang
Department of Emergency, State Key Laboratory of Biotherapy, West China Hospital, and School of Chemical Engineering, Sichuan University, No. 17 Renmin Nan Road, Chengdu, 610041 China
Search for more papers by this authorSheng-Nan Su
Department of Emergency, State Key Laboratory of Biotherapy, West China Hospital, and School of Chemical Engineering, Sichuan University, No. 17 Renmin Nan Road, Chengdu, 610041 China
Search for more papers by this authorRong Shi
Department of Emergency, State Key Laboratory of Biotherapy, West China Hospital, and School of Chemical Engineering, Sichuan University, No. 17 Renmin Nan Road, Chengdu, 610041 China
Search for more papers by this authorZe-Dong Mou
Department of Emergency, State Key Laboratory of Biotherapy, West China Hospital, and School of Chemical Engineering, Sichuan University, No. 17 Renmin Nan Road, Chengdu, 610041 China
Search for more papers by this authorGuo-Qiang Yu
Discovery Chemistry Unit, HitGen Inc., Building 6, No. Huigu 1st East Road, Tianfu International Bio-Town, Shuangliu District, Chengdu, 610200 China
Search for more papers by this authorCorresponding Author
Prof. Xia Zhang
Department of Emergency, State Key Laboratory of Biotherapy, West China Hospital, and School of Chemical Engineering, Sichuan University, No. 17 Renmin Nan Road, Chengdu, 610041 China
Search for more papers by this authorCorresponding Author
Prof. Dawen Niu
Department of Emergency, State Key Laboratory of Biotherapy, West China Hospital, and School of Chemical Engineering, Sichuan University, No. 17 Renmin Nan Road, Chengdu, 610041 China
Search for more papers by this authorWeidong Shang
Department of Emergency, State Key Laboratory of Biotherapy, West China Hospital, and School of Chemical Engineering, Sichuan University, No. 17 Renmin Nan Road, Chengdu, 610041 China
Search for more papers by this authorSheng-Nan Su
Department of Emergency, State Key Laboratory of Biotherapy, West China Hospital, and School of Chemical Engineering, Sichuan University, No. 17 Renmin Nan Road, Chengdu, 610041 China
Search for more papers by this authorRong Shi
Department of Emergency, State Key Laboratory of Biotherapy, West China Hospital, and School of Chemical Engineering, Sichuan University, No. 17 Renmin Nan Road, Chengdu, 610041 China
Search for more papers by this authorZe-Dong Mou
Department of Emergency, State Key Laboratory of Biotherapy, West China Hospital, and School of Chemical Engineering, Sichuan University, No. 17 Renmin Nan Road, Chengdu, 610041 China
Search for more papers by this authorGuo-Qiang Yu
Discovery Chemistry Unit, HitGen Inc., Building 6, No. Huigu 1st East Road, Tianfu International Bio-Town, Shuangliu District, Chengdu, 610200 China
Search for more papers by this authorCorresponding Author
Prof. Xia Zhang
Department of Emergency, State Key Laboratory of Biotherapy, West China Hospital, and School of Chemical Engineering, Sichuan University, No. 17 Renmin Nan Road, Chengdu, 610041 China
Search for more papers by this authorCorresponding Author
Prof. Dawen Niu
Department of Emergency, State Key Laboratory of Biotherapy, West China Hospital, and School of Chemical Engineering, Sichuan University, No. 17 Renmin Nan Road, Chengdu, 610041 China
Search for more papers by this authorDedicated to Professor Thomas R. Hoye on the occasion of his 70th birthday.
Abstract
We here report glycosyl sulfoxides appended with an aryl iodide moiety as readily available, air and moisture stable precursors to glycosyl radicals. These glycosyl sulfoxides could be converted to glycosyl radicals by way of a rapid and efficient intramolecular radical substitution event. The use of this type of precursors enabled the synthesis of various complex C-linked glycoconjugates under mild conditions. This reaction could be performed in aqueous media and is amenable to the synthesis of glycopeptidomimetics and carbohydrate-DNA conjugates.
Conflict of interest
The authors declare no conflict of interest.
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