Stereoselective chemical N-glycoconjugation of amines via CO2 incorporation

Zihan Peng, Qian Xiao, Yan Xia, Mingyu Xia, Jia Yu, Pengfei Fang, Yu Tang () and Biao Yu ()
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Zihan Peng: Chinese Academy of Sciences
Qian Xiao: Chinese Academy of Sciences
Yan Xia: Chinese Academy of Sciences
Mingyu Xia: Chinese Academy of Sciences
Jia Yu: Chinese Academy of Sciences
Pengfei Fang: Chinese Academy of Sciences
Yu Tang: Chinese Academy of Sciences
Biao Yu: Chinese Academy of Sciences

Nature Communications, 2024, vol. 15, issue 1, 1-11

Abstract: Abstract Chemical N-glycoconjugation can provide a unique way to tailor the properties of the ubiquitous amines for further expending their diverse functions and applications. Nevertheless, effective methodology for glycoconjugation of amines remains largely underdeveloped. Inspired by a biotransformation pathway of amine-containing drugs in vivo, we have developed an effective protocol that enables one-step chemical N-glycoconjugation of amines in high stereoselectivity under mild conditions. This protocol involves conversion of the amine moiety into the corresponding carbamate anion under CO2 atmosphere and a subsequent SN2 type reaction with glycosyl halides. This work provides an example of using CO2 as the coupling unit in chemical glycoconjugation reactions. A case study on the resulting N-glycoconjugates of Crizotinib, an anticancer drug, demonstrates a quick cleavage of the glucosyl carbamate linkage, testifying that this N-glyconjugation method could serve as a general approach to procure novel prodrugs.

Date: 2024
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DOI: 10.1038/s41467-024-54523-4

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