Total Synthesis and Neuritogenic Activity Evaluation of Ganglioside PNG‐2A from the Starfish Protoreaster nodosus1. Issue 10 (7th September 2015)

• Record Type: Journal Article
• Authors: Goto, Kenta; Suzuki, Tatsuya; Tamai, Hideki; Ogawa, Junya; Imamura, Akihiro; Ando, Hiromune; Ishida, Hideharu; Kiso, Makoto
• Is Part Of: Asian journal of organic chemistry. Volume 4:Issue 10(2015:Oct.)
• Page Start: 1160
• Page End: 1171
• Publication Date: 2015-09-07
• Subjects: Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.201500282
• Languages: English
• ISSNs: 2193-5807

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>The total synthesis of ganglioside PNG‐2A from the starfish <italic>Protoreaster nodosus</italic> and its neuritogenic activity toward neuron‐like cells is described. The unique galactose‐enriched glycan moiety, in which an 8‐<italic>O</italic>‐methyl sialic acid residue is sandwiched between galactose residues, was constructed through an efficient 8‐<italic>O</italic>‐methylation and subsequent di‐<italic>tert</italic>‐butylsilylene‐assisted α‐glycosylation at the 4‐OH of the sialic acid residue with a Gal<italic>f</italic>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).</p> </abstract>