Related Experiment Video
Updated: Jun 1, 2026

Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation
Published on: August 1, 2018
Native N-glycopeptide thioester synthesis through N→S acyl transfer
Bhavesh Premdjee1, Anna L Adams, Derek Macmillan
1Department of Chemistry, University College London, 20 Gordon Street, London WC1H 0AJ, UK.
This study shows that forming peptide thioesters using native N-glycopeptides is compatible with N→S acyl transfer. This method simplifies the synthesis of homogeneous glycoproteins, overcoming challenges with sugar moiety stability.
Area of Science:
- Biochemistry
- Organic Chemistry
- Glycobiology
Background:
- Peptide thioesters are crucial for protein synthesis via native chemical ligation (NCL).
- Synthesizing glycopeptide thioesters for homogeneous glycoproteins is challenging due to the perceived instability of sugar groups.
Purpose of the Study:
- To demonstrate the compatibility of thioester formation with native N-glycopeptides.
- To provide insights aiding the preparation of glycopeptide thioesters.
Main Methods:
- Utilizing N→S acyl transfer for thioester formation.
- Working with native N-glycopeptides.
Main Results:
- Successful thioester formation was achieved with native N-glycopeptides.
- Key observations were made to facilitate glycopeptide thioester preparation.
Conclusions:
- N→S acyl transfer is a viable method for preparing glycopeptide thioesters.
- This research simplifies the synthesis of homogeneous glycoproteins.
More Related Videos
08:46Regioselective 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
08:16Visualizing Intracellular Sialylation with Click Chemistry and Expansion Microscopy
Published on: February 7, 2025
Related Concept Videos
Peptidoglycan Synthesis
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis
Nucleophilic Acyl Substitution of Carboxylic Acid Derivatives
Preparation of Nitriles
Protein Glycosylation
Glycosylation occurs in...
Alkylation of β-Diester Enolates: Malonic Ester Synthesis