Studies on the alpha-(1-->4)- and alpha-(1-->8)-fucosylation of sialic acid for the total assembly of the glycan portions of complex HPG-series gangliosides.
A synthetic study on alpha-(1-->4) and alpha-(1-->8)-fucosylation of sialic acid is reported, with the ultimate aim being the total assembly of the glycan portion of HPG-series gangliosides. In both types of fucosylations, the combination of a phenylthio fucosyl donor and a 1,5-lactamized acceptor provided high-yielding glycosylations to afford alpha-fucosyl-sialic acid sequences. The obtained alpha-Fucp-(1-->8)-NeupNAc glycan having a 1,5-lactam bridge has been successfully transformed into the corresponding glycosyl donor.
Ando
Hiromune
H
Division of Instrumental Analysis, Life Science Research Center, Gifu University, 1-1 Yanagido, Gifu-shi, Gifu 501-1193, Japan. hando@cc.gifu-u.ac.jp
Shimizu
Hiroyo
H
Katano
Yukari
Y
Koike
Yusuke
Y
Koizumi
Sachiko
S
Ishida
Hideharu
H
Kiso
Makoto
M
D002240:Carbohydrate Sequence; D005643:Fucose / Q000737:chemistry*; D005732:Gangliosides / Q000138:chemical synthesis*; D006031:Glycosylation; D008969:Molecular Sequence Data; D019158:N-Acetylneuraminic Acid / Q000737:chemistry*
D005732:Gangliosides; C406444:HPG-7 ganglioside; D005643:Fucose; D019158:N-Acetylneuraminic Acid