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Related Concept Videos

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...
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...
Nucleophilic Addition to the Carbonyl Group: General Mechanism01:18

Nucleophilic Addition to the Carbonyl Group: General Mechanism

The carbonyl carbon in an aldehyde or ketone is the site of a nucleophilic attack due to its electron-deficient nature. Depending on the strength of the incoming nucleophile, the reaction occurs via different mechanistic pathways.
A stronger nucleophile can directly attack the electrophilic center, the carbonyl carbon. The HOMO orbital of the nucleophile interacts with the LUMO (π* antibonding) orbital present on the carbonyl carbon. This interaction breaks the π bond and shifts the π bonding...
Conjugate Addition to α,β-Unsaturated Carbonyl Compounds01:09

Conjugate Addition to α,β-Unsaturated Carbonyl Compounds

α,β-Unsaturated carbonyl compounds are molecules bearing a carbonyl and alkene functionality in conjugation with each other. The conjugation in the molecule leads to three resonance structures. The hybrid form exhibits two probable electrophilic sites: the carbonyl carbon and the β carbon.
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.

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Related Experiment Video

Updated: Jul 24, 2026

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

Glycosyl transfer to nitrogen via cycloaddition.

B Li1, R W Franck, G Capozzi

  • 1Department of Chemistry, Hunter College/CUNY, New York 10021, USA.

Organic Letters
|May 24, 2000
PubMed
Summary

Researchers developed a new method to add nitrogen to the anomeric carbon of carbohydrates. This novel functionalization uses cycloaddition reactions with bisheterodienes and glycals for efficient synthesis.

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Area of Science:

  • Organic Chemistry
  • Carbohydrate Chemistry
  • Synthetic Chemistry

Background:

  • The anomeric carbon of carbohydrates is a key site for functionalization.
  • Developing efficient methods for introducing nitrogen substituents is crucial in carbohydrate chemistry.

Purpose of the Study:

  • To describe the practical application of a new concept for functionalizing the anomeric carbon of carbohydrates with a nitrogen substituent.
  • To demonstrate a novel synthetic route for nitrogen-containing carbohydrate derivatives.

Main Methods:

  • Utilized bisheterodienes featuring a thiono sulfur terminus and a sulfonylimine terminus.
  • Employed cycloaddition reactions with three distinct types of glycals.
  • Focused on the stereoselective synthesis of carbohydrate derivatives.

Main Results:

  • Successfully achieved the functionalization of the anomeric carbon with a nitrogen substituent.
  • Demonstrated smooth and stereoselective cycloaddition reactions.
  • Synthesized three different glycal derivatives with the desired nitrogen incorporation.

Conclusions:

  • The described method represents a practical and effective approach for the synthesis of nitrogen-substituted carbohydrates.
  • The cycloaddition strategy offers a versatile route for accessing novel carbohydrate structures.
  • This work advances the field of carbohydrate functionalization and synthetic methodology.