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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...

Biosynthesis of Polysaccharides

Biosynthesis of Polysaccharides

Polysaccharides such as glycogen and starch are synthesized from nucleoside diphosphate sugars, primarily uridine diphosphate glucose (UDPG) and adenosine diphosphate glucose (ADPG). These activated glucose donors act as key intermediates in carbohydrate metabolism and biosynthesis. UDPG primarily involves glycogen synthesis in animals and many bacteria, while ADPG plays a fundamental role in starch synthesis in plants and certain bacteria.UDPG is formed when glucose-1-phosphate reacts with...

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 observed.

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.

Crossed Aldol Reactions: Overview

Crossed Aldol Reactions: Overview

Crossed aldol addition is the reaction between two different carbonyl compounds under acidic or basic conditions. Here, both the carbonyl compounds function as nucleophiles and electrophiles. As shown in Figure 1, such a reaction yields a mixture of products, two of which are formed via self-condensation, while the remaining two are formed via crossed-condensation. Without adjustment, the reaction's usefulness in organic chemistry is decreased.

Preparation of Diols and Pinacol Rearrangement

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: May 29, 2026

Hierarchical and Programmable One-Pot Oligosaccharide Synthesis

Hierarchical and Programmable One-Pot Oligosaccharide Synthesis

Published on: September 6, 2019

Reverse orthogonal strategy for oligosaccharide synthesis.

Kohki Fujikawa¹, N Vijaya Ganesh, Yih Horng Tan

¹Department of Chemistry and Biochemistry, University of Missouri-St. Louis, One University Boulevard, St. Louis, Missouri 63121, USA.

Chemical Communications (Cambridge, England)

|September 6, 2011

Summary

A new reverse strategy for oligosaccharide synthesis was developed. This method utilizes orthogonal protecting groups for efficient assembly, offering an alternative to classic approaches.

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Hierarchical and Programmable One-Pot Oligosaccharide 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
Glycoscience

Background:

Oligosaccharide synthesis is crucial for understanding biological processes.
Traditional synthesis relies on orthogonal leaving groups, which can be complex.
A need exists for more efficient and streamlined synthetic methodologies.

Purpose of the Study:

To introduce a novel, expeditious concept for oligosaccharide synthesis.
To present a reverse strategy employing orthogonal protecting groups.
To demonstrate efficient oligosaccharide assembly in the reverse direction.

Main Methods:

Development of a reverse synthesis approach.
Utilizing orthogonal protecting groups: p-methoxybenzyl (PMB) and 4-pentenoyl.
Applying these protecting groups to facilitate stepwise oligosaccharide assembly.

Main Results:

Successful implementation of the reverse oligosaccharide synthesis concept.
Demonstrated efficiency in assembling oligosaccharides using the PMB and 4-pentenoyl protecting groups.
The novel approach offers advantages over traditional methods.

Conclusions:

The developed reverse strategy provides an efficient alternative for oligosaccharide synthesis.
Orthogonal protecting groups enable streamlined assembly of complex carbohydrate structures.
This work advances the field of synthetic carbohydrate chemistry.