Related Experiment Video
Updated: Jul 17, 2026
14:37
High-throughput Synthesis of Carbohydrates and Functionalization of Polyanhydride Nanoparticles
Published on: July 6, 2012
A general strategy for stereoselective glycosylations
Jin-Hwan Kim1, Hai Yang, Jin Park
1Complex Carbohydrate Research Center, University of Georgia, 315 Riverbend Road, Athens, Georgia 30602, USA.
Journal of the American Chemical Society
|August 25, 2005
Summary
A novel method using a phenyl-phenylsulfanyl ethyl group enables stereoselective synthesis of alpha-glycosides. This breakthrough facilitates routine oligosaccharide synthesis, including crucial structures like the Galili trisaccharide for transplantation research.
Area of Science:
- Carbohydrate Chemistry
- Organic Synthesis
- Glycosylation
Background:
- Stereoselective synthesis of glycosidic linkages is a major challenge in oligosaccharide preparation.
- Existing methods often lack generality and efficiency for complex structures.
Purpose of the Study:
- To develop a general and stereoselective method for forming alpha-glycosidic linkages.
- To introduce a new protecting/activating group for glycosyl donors.
- To enable routine synthesis of biologically important oligosaccharides.
Main Methods:
- Utilizing a (1S)-phenyl-2-(phenylsulfanyl)ethyl moiety at C-2 of a glycosyl donor for neighboring group participation.
- Formation of a trans-decalin sulfonium ion intermediate.
- Stereoselective displacement of the sulfonium ion by a hydroxyl group.
- NMR spectroscopy to confirm intermediate structures.
- Introduction and removal of the moiety using specific reagents (BF(3)-OEt(2)).
Main Results:
- Stereoselective formation of alpha-glycosides via a sulfonium ion intermediate.
- Demonstration of the moiety's introduction and removal under mild conditions.
- Successful synthesis of the Galili trisaccharide using a one-pot, two-step sequence.
- Combination of the new method with ester-based neighboring group participation for versatile oligosaccharide synthesis.
Conclusions:
- The developed methodology provides a general approach for stereoselective alpha-glycoside formation.
- This method, coupled with existing techniques, allows for routine and versatile oligosaccharide synthesis.
- The synthesis of the Galili trisaccharide highlights the practical utility of this new strategy in preparing biologically relevant molecules.
Related Concept Videos
01:30Enzyme Inhibition
Inhibitors are molecules that reduce enzyme activity by binding to the enzyme. In a normally functioning cell, enzymes are regulated by a variety of inhibitors. Drugs and other toxins can also inhibit enzymes. Some inhibitors bind to the enzyme’s active site, while others inhibit enzymatic activity by binding to other sites on the protein structure.
01:27Glucose Transporters
Glucose transporters facilitate the transport of glucose across the cell membrane. In addition to glucose, some glucose transporters can also aid the movement of other hexoses such as fructose, mannose, and galactose.
Facilitated diffusion-glucose transporters (GLUTs) are encoded by the solute-linked carrier (SLC) family 2, subfamily A gene family, or SLC2A. The 14 GLUT protein members are distributed into three classes:
Facilitated diffusion-glucose transporters (GLUTs) are encoded by the solute-linked carrier (SLC) family 2, subfamily A gene family, or SLC2A. The 14 GLUT protein members are distributed into three classes:
01:22Bioreactor Controls-III
Strain improvement is a foundational strategy in industrial microbiology aimed at maximizing microbial productivity, particularly because natural isolates typically yield commercially valuable products in very low concentrations. Although optimizing the culture medium and environmental conditions can improve yields, these adjustments are inherently limited by the organism’s genetic potential. As a result, the focus shifts toward genetic modifications to enhance biosynthetic capacity. The...