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- Title
The Total Synthesis of Starfish Ganglioside GP3 Bearing a Unique Sialyl Glycan Architecture.
- Authors
Goto, Kenta; Sawa, Maki; Tamai, Hideki; Imamura, Akihiro; Ando, Hiromune; Ishida, Hideharu; Kiso, Makoto
- Abstract
The total synthesis of ganglioside GP3, which is found in the starfish Asterina pectinifera, has been accomplished through stereoselective and effective glycosylation reactions. The sialic acid embedded octasaccharide moiety of the target compound was constructed by [4+4] convergent coupling. A tetrasaccharyl donor and acceptor that contained internal sialic acid residues were synthesized with an orthogonally protected N-Troc sialic acid donor as the key common synthetic unit, and they underwent highly stereoselective glycosidation. The resulting sialosides were subsequently transformed into reactive glycosyl acceptors. [4+4] coupling furnished the octasaccharide framework in 91 % yield as a single stereoisomer. Final conjugation of the octasaccharyl donor and glucosyl ceramide acceptor produced the protected target compound in high yield, which underwent global deprotection to successfully deliver ganglioside GP3.
- Subjects
CHEMICAL synthesis; GANGLIOSIDES; GLYCANS; STEREOSELECTIVE reactions; GLYCOSYLATION
- Publication
Chemistry - A European Journal, 2016, Vol 22, Issue 24, p8323
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201600970