Efficient assembly of oligomannosides using the hydrophobically assisted switching phase method.
Shuai Meng1, Tian Tian, Dong Han
1The State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100191, China. zjli@bjmu.edu.cn.
Organic & Biomolecular Chemistry
|May 14, 2015
Summary
The hydrophobically assisted switching phase (HASP) method efficiently synthesizes complex mannose-based carbohydrates. This study optimized a novel mannosyl donor for HASP, enabling the assembly of branched oligosaccharides like penta-mannosides.
Area of Science:
- Carbohydrate Chemistry
- Organic Synthesis
- Glycoscience
Background:
- Oligomannosides are important glycans with diverse biological roles.
- Efficient synthesis of complex oligosaccharides remains a challenge.
- The hydrophobically assisted switching phase (HASP) method offers a promising approach for glycosidic bond formation.
Purpose of the Study:
- To optimize and apply the hydrophobically assisted switching phase (HASP) method for oligomannoside synthesis.
- To develop a highly reactive mannosyl donor suitable for the HASP method.
- To explore the utility of HASP for assembling branched oligosaccharides.
Main Methods:
- Optimization studies to identify a suitable mannosyl donor.
- Application of the hydrophobically assisted switching phase (HASP) method for glycosylation.
- Synthesis and characterization of target oligomannosides, including branched structures.
Main Results:
- A novel, highly reactive mannosyl donor was identified and optimized.
- The HASP method was successfully applied to synthesize oligomannosides.
- Two branched penta-mannosides were efficiently assembled using the optimized HASP protocol.
Conclusions:
- The hydrophobically assisted switching phase (HASP) method is effective for synthesizing complex oligomannosides.
- The developed mannosyl donor enhances the efficiency of HASP-mediated glycosylation.
- HASP is a practical method for the construction of branched oligosaccharides.
