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Updated: Nov 5, 2025

Targeting Cysteine Thiols for in Vitro Site-specific Glycosylation of Recombinant Proteins
Published on: October 4, 2017
Exploring glycosyl sulphates as donors for chemical glycosylation
Daniela Imperio1, Federica Campo1, Luigi Panza1
1Università del Piemonte Orientale, Dipartimento di Scienze del Farmaco, L.go Donegani 2, 28100 Novara, Italy. daniela.imperio@uniupo.it.
Abstract:
The preparation of anomeric tetrabutylammonium sulphates of glucose and galactose derivatives is reported and their role as donors in glycosylation reactions is studied. Metal triflates showed good performance in activating sulphate as a leaving group. Among them, ytterbium triflate in stoichiometric amounts gave the best results. Basic conditions using barium oxide in combination with trimethylsilyl trifluoromethanesulfonate (TMSOTf) were also shown to give good results. Benzylated sulphates were much more reactive than benzoylated donors when activated either by ytterbium triflate or by BaO and TMSOTf. Different acceptors were tested, such as isopropanol, cholesterol, and other common sugar derivatives. High reaction rates and excellent glycosylation yields were obtained under mild reaction conditions. The α/β anomeric ratio suggests a predominant SN2-like reaction mechanism.
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