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Protein Glycosylation

Protein Glycosylation

Glycosylation, the most common post-translational modification for proteins, serves diverse functions. Adding sugars to proteins makes the proteins more resistant to proteolytic digestion. Glycosylated proteins can act as markers and receptors to promote cell-cell adhesion. Additionally, they have many essential quality control functions in the cell, such as correct protein folding and facilitating transport of misfolded proteins to the cytosol, which can be degraded.
Glycosylation occurs in...

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...

SN2 Reaction: Stereochemistry

S_N2 Reaction: Stereochemistry

In an SN2 reaction, the nucleophilic attack on the substrate and departure of the leaving group occurs simultaneously through a transition state. As the nucleophile approaches the substrate from the back-side, the configuration of the substrate carbon changes from tetrahedral to trigonal bipyramidal and then back to tetrahedral, leading to an inversion in the configuration of the product.
If the substrate is an achiral molecule at the α-carbon, the inversion of configuration is not...

SN1 Reaction: Stereochemistry

S_N1 Reaction: Stereochemistry

This lesson provides an in-depth discussion of the stereochemical outcomes in an SN1 reaction.
In the first step of an SN1 reaction, the bond between the electrophilic carbon and the leaving group ionizes to generate the carbocation intermediate. The second step of the mechanism is the nucleophilic attack.
In the formed carbocation, the positively charged carbon is sp2 hybridized with a trigonal planar geometry. As all the three substituents lie on the same plane, a plane of symmetry for the...

Regioselectivity and Stereochemistry of Hydroboration

Regioselectivity and Stereochemistry of Hydroboration

A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.

Proteoglycans

Proteoglycans

Glycans, a class of complex heterogeneous molecules, can be covalently attached to proteins to form glycosylated proteins that regulate various physiological and pathological processes. Glycosylated proteins or glycoproteins comprise N-linked and O-linked oligosaccharides. O-glycosylation is the most common type of protein glycosylation. Here, glycans attach to the oxygen atom of the hydroxyl groups of Serine or Threonine residues. O-linked glycosylation occurs later in protein processing,...

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Related Experiment Video

Updated: Jan 19, 2026

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

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

Published on: July 26, 2018

Recent Developments in Stereoselective Chemical Glycosylation.

Jesse Ling¹, Clay S Bennett¹

¹Department of Chemistry, Tufts University, 62 Talbot Ave., Medford, MA 02155, USA.

Asian Journal of Organic Chemistry

|September 20, 2019

Summary

Chemists are developing new methods for synthesizing complex sugars (oligosaccharides) to meet growing biological research demands. Recent advances focus on stereoselective chemical glycosylation techniques, improving synthesis efficiency and control.

Keywords:

carbohydrates diastereoselectivity glycosides glycosylation oligosaccharides

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Last Updated: Jan 19, 2026

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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Area of Science:

Carbohydrate Chemistry
Organic Synthesis
Glycobiology

Background:

Growing demand for homogeneous oligosaccharides due to their critical biological functions.
Chemical synthesis of oligosaccharides remains a significant challenge in organic chemistry.
Recent decades have seen rapid advancements in the field of glycobiology.

Purpose of the Study:

To provide an overview of the latest trends in chemical glycosylation.
To highlight stereoselective synthetic protocols developed over the past decade.
To address the challenges in synthesizing homogeneous oligosaccharides.

Main Methods:

Review of novel catalytic systems for glycosylation.
Application of glycosylation modulators to control stereoselectivity.
Utilizing photochemical energy to facilitate glycosylation reactions.

Main Results:

Significant progress in stereoselective oligosaccharide synthesis.
Development of new catalytic approaches and glycosylation strategies.
Transformation of the field through innovative methods and reinvestigated traditional techniques.

Conclusions:

The field of chemical glycosylation has been significantly advanced by recent innovations.
Stereoselective synthesis of oligosaccharides is becoming more accessible and efficient.
Continued research in chemical glycosylation is crucial for glycobiology and related fields.