Synthesis of Lipid-Linked Oligosaccharides (LLOs) and Their Phosphonate Analogues as Probes To Study Protein Glycosylation Enzymes

Here we review chemical and chemoenzymatic methods for the synthesis of lipid-linked oligosaccharides (LLOs) and their phosphonate analogues, which serve as substrates and inhibitors to investigate the structure and mechanism of protein N-glycosylation enzymes. We emphasize how to overcome the challenges pertaining to the instability and difficult physicochemical properties of this class of compounds.1 Introduction2 LLO Syntheses2.1 Glycosyl Phosphate Syntheses2.2 Glycosyl Phosphonates2.3 Lipid Elongation2.4 Lipid Phosphates2.5 Coupling Reaction Strategies3 Chemoenzymatic Synthesis of Elongated LLOs4 Biological Properties of Synthetic LLOs5 Conclusion

One-pot conversion reactions of glycosyl boranophosphates into glycosyl phosphate derivatives via acyl phosphite intermediates

One-pot conversion reactions of glycosyl boranophosphate into glycosyl phosphate derivatives under mild basic conditions.

Automated solid-phase synthesis of oligosaccharides containing sialic acids

A sialic acid glycosyl phosphate building block was designed and synthesized. This building block was used to prepare α-sialylated oligosaccharides by automated solid-phase synthesis selectively.