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Stereoselective chemical N-glycoconjugation of amines via CO2 incorporation

Author

Listed:
  • 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
    Shenyang Pharmaceutical University)

  • Pengfei Fang

    (Chinese Academy of Sciences)

  • Yu Tang

    (Chinese Academy of Sciences)

  • Biao Yu

    (Chinese Academy of Sciences)

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.

Suggested Citation

  • Zihan Peng & Qian Xiao & Yan Xia & Mingyu Xia & Jia Yu & Pengfei Fang & Yu Tang & Biao Yu, 2024. "Stereoselective chemical N-glycoconjugation of amines via CO2 incorporation," Nature Communications, Nature, vol. 15(1), pages 1-11, December.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-54523-4
    DOI: 10.1038/s41467-024-54523-4
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    References listed on IDEAS

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    1. Qiuhan Li & Samuel M. Levi & Corin C. Wagen & Alison E. Wendlandt & Eric N. Jacobsen, 2022. "Site-selective, stereocontrolled glycosylation of minimally protected sugars," Nature, Nature, vol. 608(7921), pages 74-79, August.
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