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Updated: Aug 27, 2025
09:56
Hierarchical and Programmable One-Pot Oligosaccharide Synthesis
Published on: September 6, 2019
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Design, Synthesis, and Characterization of Stapled Oligosaccharides.
Manuel G Ricardo1, Emelie E Reuber1,2, Ling Yao1
1Department of Biomolecular Systems, Max-Planck-Institute of Colloids and Interfaces, Am Muehlenberg 1, 14476 Potsdam, Germany.
Journal of the American Chemical Society
|September 29, 2022
Summary
Researchers developed the first stapled oligosaccharides by cross-linking glucans. This novel glycan modification enhances stability and cell penetration for improved medicinal chemistry applications.
Area of Science:
- Carbohydrate Chemistry
- Medicinal Chemistry
- Biotechnology
Background:
- Peptide stapling is a known technique to stabilize conformations and improve drug properties.
- Oligosaccharides are complex carbohydrates with therapeutic potential but lack conformational stabilization methods.
Purpose of the Study:
- To design, synthesize, and characterize the first stapled oligosaccharides.
- To explore the potential of stapled oligosaccharides in medicinal chemistry.
Main Methods:
- Automated assembly of beta-(1,6)-glucans with alkenyl side chains.
- On-resin ring-closing metathesis using Grubbs catalyst.
- Characterization of the resulting stapled oligosaccharide structures.
Main Results:
- Successful synthesis of the first stapled oligosaccharides.
- Demonstrated increased enzymatic stability compared to non-stapled counterparts.
- Enhanced cell penetration capabilities of the stapled glycans.
Conclusions:
- Oligosaccharide stapling is a viable strategy for enhancing glycan properties.
- This technique opens new avenues for glycan-based therapeutics.
- Stapled glycans offer improved stability and delivery for medicinal applications.
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