Abstract
AbstractThe total synthesis of ganglioside PNG‐2A from the starfish Protoreaster nodosus and its neuritogenic activity toward neuron‐like cells is described. The unique galactose‐enriched glycan moiety, in which an 8‐O‐methyl sialic acid residue is sandwiched between galactose residues, was constructed through an efficient 8‐O‐methylation and subsequent di‐tert‐butylsilylene‐assisted α‐glycosylation at the 4‐OH of the sialic acid residue with a Galfβ(1,3)Gal donor. In vitro biological evaluation in a rat adrenal pheochromocytoma (PC12) cell line revealed that the synthesized PNG‐2A potentiated the neurite outgrowth of PC12 cells in the presence of nerve growth factor (NGF).
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