Ready access to sialylated oligosaccharide donors

Area of Science:

• Carbohydrate Chemistry
• Glycobiology
• Synthetic Organic Chemistry

Background:

• The disaccharide Neu5Ac alpha (2-->3)DGalp is a crucial component in numerous biologically significant glycoconjugates.
• Efficient synthesis of complex glycoconjugates relies on the availability of well-defined building blocks.

Purpose of the Study:

• To develop a streamlined chemoenzymatic route for synthesizing the Neu5Ac alpha (2-->3)DGalp disaccharide building block.
• To demonstrate the utility of this building block in the preparation of synthetic trisaccharides.

Main Methods:

• A chemoenzymatic strategy was employed, requiring only four synthetic steps.
• Alternative synthetic routes with increased chemical steps were explored to enhance flexibility.
• The synthesized disaccharide donors were utilized in subsequent glycosylation reactions.

Main Results:

• An efficient four-step chemoenzymatic synthesis of the target disaccharide building block was achieved.
• The developed building blocks were successfully employed in the synthesis of novel trisaccharides.
• The methodology offers a flexible approach to incorporate the disaccharide into various synthetic glycoconjugates.

Conclusions:

• The reported chemoenzymatic route provides an efficient and accessible method for preparing the Neu5Ac alpha (2-->3)DGalp disaccharide building block.
• This building block is valuable for the synthesis of complex glycoconjugates and oligosaccharides.
• The study highlights the power of combining chemical and enzymatic approaches in carbohydrate synthesis.