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Oligosaccharide Assembly01:24

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...
Alkylation of β-Diester Enolates: Malonic Ester Synthesis01:14

Alkylation of β-Diester Enolates: Malonic Ester Synthesis

Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.
Cationic Chain-Growth Polymerization: Mechanism00:57

Cationic Chain-Growth Polymerization: Mechanism

The cationic polymerization mechanism consists of three steps: initiation, propagation, and termination. In the initiation step of the polymerization process, the π bond of a monomer gets protonated by the Lewis acid catalyst, which is formed from boron trifluoride and water. The protonation of the π bond generates a carbocation stabilized by the electron‐donating group. In the propagation step, the π bond of the second monomer acts as a nucleophile and attacks the generated carbocation,...
Protein Glycosylation01:25

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...
Anionic Chain-Growth Polymerization: Overview01:20

Anionic Chain-Growth Polymerization: Overview

The polymerization process that involves carbanion as an intermediate is called anionic polymerization. It is also a type of addition or chain-growth polymerization. Anionic polymerization gets initiated by a strong nucleophile such as an organolithium or a Grignard reagent. The most commonly used initiator for anionic polymerization is butyl lithium. Monomers involved in anionic polymerization must possess a vinyl group bonded to one or two electron-withdrawing groups. For instance,...
Preparation of Diols and Pinacol Rearrangement01:57

Preparation of Diols and Pinacol Rearrangement

Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.

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Related Experiment Video

Updated: Jul 9, 2026

Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides
08:46

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

Oligomannan synthesis using ionic liquid supported glycosylation.

Ashish K Pathak1, Charu K Yerneni, Zac Young

  • 1Department of Chemistry, Western Illinois University, Macomb, Illinois 61455, USA. ak-pathak@wiu.edu

Organic Letters
|December 12, 2007
PubMed
Summary

Researchers developed a new method for synthesizing complex oligosaccharides using ionic liquid support. This approach efficiently produces linear alpha(1-->6) oligomannan thioglycosides without extensive purification.

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High-throughput Synthesis of Carbohydrates and Functionalization of Polyanhydride Nanoparticles

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Related Experiment Videos

Last Updated: Jul 9, 2026

Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides
08:46

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

Hierarchical and Programmable One-Pot Oligosaccharide Synthesis
09:56

Hierarchical and Programmable One-Pot Oligosaccharide Synthesis

Published on: September 6, 2019

High-throughput Synthesis of Carbohydrates and Functionalization of Polyanhydride Nanoparticles
14:37

High-throughput Synthesis of Carbohydrates and Functionalization of Polyanhydride Nanoparticles

Published on: July 6, 2012

Area of Science:

  • Carbohydrate Chemistry
  • Organic Synthesis
  • Glycosylation Chemistry

Background:

  • The synthesis of complex oligosaccharides remains a significant challenge in chemical research.
  • Efficient and scalable methods for constructing specific glycosidic linkages are highly sought after.

Purpose of the Study:

  • To develop a novel and efficient strategy for the synthesis of activated oligomannans.
  • To demonstrate the utility of ionic liquid (IL) support in glycosylation reactions.

Main Methods:

  • Utilized an ionic liquid (IL) support strategy for glycosylation.
  • Employed an IL-tagged mannosyl fluoride donor for the synthesis of oligomannans.
  • Focused on the formation of linear alpha(1-->6) linkages.

Main Results:

  • Successfully synthesized activated oligomannan 1.
  • Demonstrated rapid production of linear alpha(1-->6) oligomannan thioglycosides.
  • Eliminated the need for column purification after each glycosylation step, improving convenience and cost-effectiveness.

Conclusions:

  • The developed ionic liquid support glycosylation methodology offers a convenient and cost-effective approach for synthesizing linear alpha(1-->6) oligomannan thioglycosides.
  • This strategy simplifies the purification process, making complex oligosaccharide synthesis more accessible.