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Total Synthesis and Neuritogenic Activity Evaluation of Ganglioside PNG‐2A from the Starfish Protoreaster nodosus
Author(s) -
Goto Kenta,
Suzuki Tatsuya,
Tamai Hideki,
Ogawa Junya,
Imamura Akihiro,
Ando Hiromune,
Ishida Hideharu,
Kiso Makoto
Publication year - 2015
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201500282
Subject(s) - chemistry , starfish , ganglioside , sialic acid , neurite , galactose , glycosylation , moiety , total synthesis , glycan , biochemistry , nerve growth factor , in vitro , residue (chemistry) , glycoprotein , stereochemistry , receptor , ecology , biology
The 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 Gal f β(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).