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Updated: Jun 13, 2025

Targeting Cysteine Thiols for in Vitro Site-specific Glycosylation of Recombinant Proteins
Published on: October 4, 2017
Highly Reactive Glycosylation with 1-O-(Methylthio)thiocarbonyl Glycosyl Donors under Acidic to Neutral Reaction
Tao Luo1, Guo-Hui Zhang1, Yang-Fan Guo1
1Key Laboratory of Material Chemistry for Energy Conversion and Storage, Ministry of Education, Hubei Key Laboratory of Bioinorganic Chemistry and Materia Medica, School of Chemistry & Chemical Engineering, Huazhong University of Science & Technology, Luoyu Road 1037, Wuhan 430074, P. R. China.
Abstract:
In this study, we have successfully developed a glycosylation method using 1-O-(methylthio)thiocarbonyl-glycoses as donors. Such xanthate donors are easily accessible and shelf-stable. The glycosylation reaction could be promoted by cations (acidic to neutral conditions) under mild conditions, exhibiting a reactivity intermediate between that with glycosyl trichloroacetimidate as the donor and that with thioglycoside as the donor. This methodology tolerates both "armed" and "disarmed" glycosyl donors, as well as various sugar acceptors, and affords the corresponding glycosides in good to excellent yields. Based on the relative higher reactivity of such xanthate donors than thioglycoside donors under the same glycosylation conditions, a trisaccharide was further synthesized in a one-pot glycosylation strategy.
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