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The Total Synthesis of Starfish Ganglioside GP3 Bearing a Unique Sialyl Glycan Architecture
Author(s) -
Goto Kenta,
Sawa Maki,
Tamai Hideki,
Imamura Akihiro,
Ando Hiromune,
Ishida Hideharu,
Kiso Makoto
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201600970
Subject(s) - sialic acid , chemistry , glycosylation , stereoselectivity , ganglioside , moiety , total synthesis , glycan , stereochemistry , glycosyl donor , glycosyl , yield (engineering) , acceptor , starfish , combinatorial chemistry , biochemistry , glycoprotein , biology , catalysis , ecology , materials science , physics , metallurgy , condensed matter physics
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.