| Autor: |
Peng, Zihan, Xiao, Qian, Xia, Yan, Xia, Mingyu, Yu, Jia, Fang, Pengfei, Tang, Yu, Yu, Biao |
| Zdroj: |
Nature Communications; 11/29/2024, Vol. 15 Issue 1, p1-11, 11p |
| Abstrakt: |
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. Effective methodology for glycoconjugation of amines remains underdeveloped. Here the authors report an effective protocol that enables one-step chemical N-glycoconjugation of amines in high stereoselectivity under mild conditions, inspired by a biotransformation pathway of amine-containing drugs in vivo. [ABSTRACT FROM AUTHOR] |
| Databáze: |
Complementary Index |
| Externí odkaz: |
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