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Phase II reactions are essential for the detoxification and elimination of drugs from the body. These reactions involve the conjugation of parent drugs or their phase I metabolites with endogenous molecules, resulting in more hydrophilic drug conjugates. The primary conjugation reactions in this phase are sulfation and glucuronidation. Both sulfation and glucuronidation typically produce biologically inactive metabolites. However, in some cases involving prodrugs, active metabolites may be...

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Related Experiment Video

Updated: Jun 1, 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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Published on: July 26, 2018

En route to sugar-alkaloid conjugates.

Carsten-Endres Sowa¹, Joachim Thiem

¹University of Hamburg, Faculty of Science, Department of Chemistry, Martin-Luther-King-Platz 6, D-20146 Hamburg, Germany.

Carbohydrate Research

|May 20, 2011

Summary

Researchers synthesized novel N-glycopyranosyl succinimides from glycals. Subsequent UV irradiation and chemical transformations yielded unique sugar conjugates with potential applications in alkaloid N-pyrrol component research.

Area of Science:

Organic Chemistry
Carbohydrate Chemistry
Synthetic Chemistry

Background:

Glycals are versatile carbohydrate precursors.
N-glycopyranosyl succinimides are important synthetic intermediates.
Novel sugar conjugates are of interest in medicinal chemistry.

Purpose of the Study:

To develop a stereoselective synthesis of N-glycopyranosyl succinimides.
To explore the photochemical and chemical transformations of these compounds.
To synthesize novel sugar conjugates with potential biological relevance.

Main Methods:

Stereoselective addition of N-iodosuccinimide to glycals.
Dehalogenation to form N-glycopyranosyl succinimides.
UV irradiation to yield azepindiones and tricyclic oxalactams.

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Thiation and reduction for further functionalization.

Main Results:

Successful synthesis of N-glycopyranosyl succinimides.
Photochemical generation of azepindiones and tricyclic oxalactams.
Formation of novel sugar conjugates resembling alkaloid N-pyrrol components.

Conclusions:

A novel synthetic route to N-glycopyranosyl succinimides was established.
UV irradiation provides access to unique heterocyclic structures.
The synthesized sugar conjugates represent new chemical entities with potential applications.