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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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Updated: Jun 4, 2025

Hierarchical and Programmable One-Pot Oligosaccharide Synthesis

Hierarchical and Programmable One-Pot Oligosaccharide Synthesis

Published on: September 6, 2019

Automated Synthesis of C1-Functionalized Oligosaccharides.

Georg B Niggemeyer¹, José A Danglad-Flores¹, Peter H Seeberger^1,2

¹Department of Biomolecular Systems, Max-Planck-Institute of Colloids and Interfaces, Potsdam 14476, Germany.

Journal of the American Chemical Society

|December 31, 2024

Summary

This summary is machine-generated.

Automated glycan assembly (AGA) now allows diverse aglycon introduction using a novel photolabile linker. This breakthrough enables versatile synthesis of complex oligosaccharides for various applications.

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Area of Science:

Carbohydrate Chemistry
Organic Synthesis
Bioconjugation

Background:

Automated glycan assembly (AGA) simplifies complex oligosaccharide synthesis.
Current AGA methods limit the introduction of diverse aglycons at the reducing end.
Oligosaccharide conjugation to proteins or surfaces is crucial for applications.

Purpose of the Study:

To develop a novel method for facile and versatile aglycon introduction in AGA.
To enable bidirectional AGA with a traceless photolabile linker.
To demonstrate the synthesis of various complex glycoconjugates.

Main Methods:

A latent-active approach utilizing a traceless photolabile linker was developed.
The linker allows for bidirectional automated glycan assembly.
Various aglycons were introduced onto the oligosaccharide scaffold.

Main Results:

Successful synthesis of oligosaccharide thioglycosides, peptidoglycans, and saponins.
Demonstrated versatility through click-chemistry-based conjugates.
The method allows for the ready introduction of diverse aglycons.

Conclusions:

The developed latent-active AGA approach overcomes previous limitations.
This method significantly enhances the versatility of oligosaccharide synthesis.
The strategy is applicable to a wide range of glycoconjugates for diverse applications.