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First Total Synthesis of Ganglioside GAA‐7 from Starfish Asterias amurensis versicolor
Author(s) -
Tamai Hideki,
Imamura Akihiro,
Ogawa Junya,
Ando Hiromune,
Ishida Hideharu,
Kiso Makoto
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500606
Subject(s) - moiety , chemistry , ganglioside , ceramide , starfish , neurite , stereochemistry , oligosaccharide , glycosylation , total synthesis , stereocenter , biochemistry , in vitro , biology , apoptosis , enantioselective synthesis , catalysis , ecology
The first total synthesis of neuritogenic ganglioside GAA‐7 was achieved using the glucosyl ceramide (Glc‐Cer) cassette approach. The stereocenter triad within the ceramide moiety of the target molecule was efficiently established from D ‐lyxose. The assembly of the ceramide moiety was followed by glycosylation with glucosyl donors to give Glc‐Cer cassettes, which underwent conjugation with the oligosaccharide moiety, followed by global deprotection. By using the most suitable Glc‐Cer cassette, the target molecule was successfully synthesized. In vitro evaluation indicated that the synthesized GAA‐7 and its glycan moiety both showed strong neuritogenic activity towards neuron‐like rat adrenal pheochromocytoma (PC12) cells in the presence of neurite growth factor.