Study on systematizing the synthesis of the a-series ganglioside glycans GT1a, GD1a, and GM1 using the newly developed N-Troc-protected GM3 and GalN intermediates.
A first systematic synthesis of the glycan parts of the a-series gangliosides (GT1a, GD1a, and GM1) utilizing the newly developed N-Troc-protected GM3 and galactosaminyl building blocks is described. The key processes, including the assembly of the GM2 sequence and its conversion into the 3-hydroxy acceptor, were facilitated mainly by the high degree of participation and chemoselective cleavability of the Troc group in the galactosaminyl unit. Furthermore, the novel GM2 acceptor served as a good coupling partner during glycosylation with galactosyl, sialyl galactosyl, and disialyl galactosyl donors, successfully producing the GM1, GD1a, and GT1a glycans.
Komori
Tatsuya
T
Department of Applied Bioorganic Chemistry, Faculty of Applied Biological Sciences, Gifu University, 1-1 Yanagido, Gifu-shi, Gifu 501-1193, Japan.
Imamura
Akihiro
A
Ando
Hiromune
H
Ishida
Hideharu
H
Kiso
Makoto
M
D000081:Acetamides; D002240:Carbohydrate Sequence; D062845:Chloroacetates; D005677:G(M1) Ganglioside / Q000138:chemical synthesis* / Q000737:chemistry; D005679:G(M3) Ganglioside / Q000737:chemistry*; D005732:Gangliosides / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D014238:Trichloroacetic Acid / Q000737:chemistry
D000081:Acetamides; D062845:Chloroacetates; D005679:G(M3) Ganglioside; D005732:Gangliosides; C021298:ganglioside, GD1a; D005677:G(M1) Ganglioside; C016481:trisialoganglioside GT1; D014238:Trichloroacetic Acid; C009528:trichloroacetamide