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Oligosaccharide Assembly

Oligosaccharide Assembly

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.
Multiple sugar molecules that may or may...

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Related Experiment Video

Updated: May 24, 2025

Solid Phase Synthesis of a Functionalized Bis-Peptide Using "Safety Catch" Methodology

Solid Phase Synthesis of a Functionalized Bis-Peptide Using "Safety Catch" Methodology

Published on: May 15, 2012

Novel Base-Labile Linkers for Convenient Purification and Functional Group Introduction in Solid-Phase Glycan

Tan Liu¹, Xin Gu^1,2, Zimiao Qin¹

¹Key Laboratory of Carbohydrate Vaccines and Drugs in Jiangsu Province, Key Laboratory of Carbohydrate Chemistry and Biotechnology of Ministry of Education, School of Life Sciences and Health Engineering, Jiangnan University, Wuxi, 214122, China.

Chemistry (Weinheim an Der Bergstrasse, Germany)

|March 4, 2025

Summary

This summary is machine-generated.

New base-labile linkers for Merrifield resin enable efficient solid-phase synthesis of pure oligosaccharides. These linkers facilitate the preparation of diverse glycans with terminal functional groups for glycoconjugate development.

Keywords:

base-labile linker carbohydrate chemistry glycan synthesis glycolipid solid-phase synthesis

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Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides

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High-throughput Synthesis of Carbohydrates and Functionalization of Polyanhydride Nanoparticles

High-throughput Synthesis of Carbohydrates and Functionalization of Polyanhydride Nanoparticles

Published on: July 6, 2012

Area of Science:

Carbohydrate Chemistry
Organic Synthesis
Biomolecular Chemistry

Background:

Glycans are vital biomolecules, but their structure-property relationships are not well understood.
Chemical synthesis of pure oligosaccharides is essential for their study.
Linkers for solid-phase synthesis are critical for efficient glycan preparation.

Purpose of the Study:

To develop and evaluate novel base-labile linkers for Merrifield resin in solid-phase glycan synthesis.
To enable the preparation of diverse oligosaccharides with defined terminal functional groups.

Main Methods:

Synthesis of three distinct base-labile linkers compatible with Merrifield resin.
Utilizing different cleavage conditions (methanolysis, hydrolysis, hydrazinolysis) to release glycans.
Solid-phase synthesis of various tetrasaccharides and an octasaccharide.

Main Results:

Developed three base-labile linkers, including a hydroxyhexanoic acid linker and phthalate-based linkers.
Demonstrated successful synthesis of glycans with terminal carboxylic acid, free reducing end, or amine functionalities.
Prepared nine tetrasaccharides and one octasaccharide, including mannan and glucan structures.
Hydrazinolysis proved advantageous for isolating pivaloyl-protected oligosaccharides, simplifying purification.

Conclusions:

The developed linkers offer versatile strategies for solid-phase oligosaccharide synthesis.
These methods facilitate the preparation of functionalized glycans for downstream applications like glycoconjugate synthesis.
The choice of linker and cleavage method impacts the final glycan product and purification efficiency.