First Total Synthesis of Ganglioside GAA‐7 from Starfish Asterias amurensis versi­color1. Issue 23 (8th July 2015)

• Record Type: Journal Article
• Authors: Tamai, Hideki; Imamura, Akihiro; Ogawa, Junya; Ando, Hiromune; Ishida, Hideharu; Kiso, Makoto
• Is Part Of: European journal of organic chemistry. Issue 23(2015)
• Page Start: 5199
• Page End: 5211
• Publication Date: 2015-07-08
• Subjects: Total synthesis -- Natural products -- Glycosylation -- Glycolipides -- Gangliosides -- Echinoderms; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201500606
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: 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 fromD ‐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. Abstract : The first total synthesis of neuritogenic ganglioside GAA‐7 was achieved using the glucosyl ceramide cassette approach. The neuritogenic activities of the synthesized GAA‐7 and its glycan moiety were also examined.