Automated Synthesis of C1-Functionalized Oligosaccharides

Area of Science:

• Carbohydrate Chemistry
• Organic Synthesis
• Bioconjugation

Background:

• Automated glycan assembly (AGA) simplifies complex oligosaccharide synthesis.
• Current AGA methods limit the introduction of diverse aglycons at the reducing end.
• Oligosaccharide conjugation to proteins or surfaces is crucial for applications.

Purpose of the Study:

• To develop a novel method for facile and versatile aglycon introduction in AGA.
• To enable bidirectional AGA with a traceless photolabile linker.
• To demonstrate the synthesis of various complex glycoconjugates.

Main Methods:

• A latent-active approach utilizing a traceless photolabile linker was developed.
• The linker allows for bidirectional automated glycan assembly.
• Various aglycons were introduced onto the oligosaccharide scaffold.

Main Results:

• Successful synthesis of oligosaccharide thioglycosides, peptidoglycans, and saponins.
• Demonstrated versatility through click-chemistry-based conjugates.
• The method allows for the ready introduction of diverse aglycons.

Conclusions:

• The developed latent-active AGA approach overcomes previous limitations.
• This method significantly enhances the versatility of oligosaccharide synthesis.
• The strategy is applicable to a wide range of glycoconjugates for diverse applications.