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Oligosaccharide Assembly

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Protein glycosylation starts in the ER lumen and continues in the Golgi apparatus. Glycosyltransferases catalyze the addition of sugar molecules or glycosylation of proteins. Usually, these enzymes add sugars to the hydroxyl groups of selected serine or threonine residues to form O-linked glycans or the amino groups of asparagine residues to form N-linked glycans. Different positions on the same polypeptide chain can contain differently linked glycans.
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Targeting Cysteine Thiols for in Vitro Site-specific Glycosylation of Recombinant Proteins

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Stereo-Switchable Electrochemical Glycosylation.

Pengyu Wang¹, Haiyang Huang², Qinghui Cai¹

¹State Key Laboratory of Natural and Biomimetic Drugs, Beijing Key Laboratory of Carbohydrate Intelligent Manufacture and Functional Applications, School of Pharmaceutical Science, Peking University, Xue Yuan Road No. 38, Beijing 100191, China.

Journal of the American Chemical Society

|April 10, 2026

Summary

This summary is machine-generated.

This study introduces a novel electrochemical glycosylation method using glycosyl imidates. It offers switchable stereoselectivity and efficient synthesis of O-glycosides and oligosaccharides, surpassing traditional methods.

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Area of Science:

Organic Chemistry
Carbohydrate Chemistry
Electrosynthesis

Background:

Stereoselective glycosylation is challenging in organic synthesis.
Electrochemical methods for glycosylation are underexplored.
Current methods often lack broad substrate scope and selectivity.

Purpose of the Study:

To develop a novel electrochemical glycosylation reaction.
To achieve switchable stereoselectivity using electrolyte composition.
To synthesize O-glycosides and oligosaccharides efficiently.

Main Methods:

Electrochemical glycosylation using glycosyl imidates.
Switching stereoselectivity by altering electrolyte composition.
Comparative analysis with conventional glycosylation techniques.

Main Results:

High yields (up to 98%) and excellent stereoselectivity for O-glycosides and oligosaccharides.
Demonstrated broad substrate scope and functional group compatibility.
Revealed aminyl radical intermediacy and the role of counterion/solvent in stereoselectivity control.

Conclusions:

The developed electrochemical method provides a robust platform for controlled carbohydrate assembly.
It offers high stereoselectivity, efficiency, and scalability.
This work highlights the potential of electrosynthesis in carbohydrate chemistry.