Ganglioside GM₃ Derivatives with Truncated Ceramide Moiety: Facial Synthesis and Inhibitory Activity against KB Cell Growth

Abstract

An expeditious sialylation reaction with phenylthioglycoside 4 as a sialyl donor and MeSOTf as a promoter was developed. These conditions are very useful for synthesizing ganglioside GM₃ (1), its C8‐ceramide analog 2, and 3‐deoxy analog 3 of 2 in an efficient manner. The GM₃ analog 2, whose hydrophilicity is increased by shortening the ceramide moiety, exhibits increased growth inhibiton of KB cells. The 3‐hydoxy group of ceramide does not influence its activity against KB cells.

Keywords:

• Ganglioside GM₃
• truncated ceramide
• inhibitory activity against KB cell growth

Acknowledgements

This work was supported by Colorado State University and Osaka University.