Synthesis of a new class of glycolipids and the evaluation of their immunogenicity using murine splenocytes

A new class of glycolipids were generated by the incorporation of lipid entities at the C-6 position of D-glucose through oxidation of the primary hydroxyl group of tetrabenzylated D-glucose to form corresponding aldehyde, which in turn was subjected to Grignard reaction with C8 and C16 alkyl magnesium halides. The resulting lipidated secondary alcohol was further subjected to esterification with long-chain carboxylic acids to afford novel glycolipids. All of the derivatives 4a–b, 6a–d, and 8a–b exhibited low cytotoxicity and induced strong T and B cell proliferation and IL-2, IL-4, and IFN-γ expression from stimulated splenocyte culture, signifying their potent immunostimulating activity.