Synthesis of Glycoconjugates through Chlorooxime–Thiol Conjugation

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Synthesis of Glycoconjugates through Chlorooxime–Thiol Conjugation

Gu, Wang; Huang, Jingrong; Lu, Yichi; Lin, Wanzhen; Xu, Wei; Chen, Fa-Jie

Journal of organic chemistry, 05/2024, Volume: 89, Issue: 9

Journal Article

Introducing glycans represents an efficient chemical approach to improve the pharmacological properties of therapeutic biomolecules. Herein, we report an efficient synthesis of glycoconjugates through chlorooxime–thiol conjugation. The reactive glycosyl chlorooximes, derived from pyranoses or furanoses, readily couple to a wide range of thiol-containing substrates, including peptides, sugars, and thiophenols. This method features mild reaction conditions and fast kinetics. Capability for aqueous media and gram-scale synthesis demonstrates the potential of this method in the bioconjugation of saccharides with biologically active molecules.

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