Chemoenzymatic synthesis of diverse asparagine-linked alpha-(2,3)-sialyloligosaccharides.
Partial sialyl transfer reaction by alpha-(2,3)-sialyltransferase toward (Gal-beta-1,4-GlcNAc-beta-1,2-Man-alpha-1,6/1,3-)(2)Man-beta-1,4-GlcNAc-beta-1,4-GlcNAc-beta-1-asparagine-Fmoc 1 was examined to obtain mono-alpha-(2,3)-sialyloligosaccharides and then branch-specific exo-glycosidase digestion (beta-D-galactosidase, N -acetyl-beta-D-glucosaminidase and alpha-D-mannosidase) toward the asialo-branch was performed to obtain diverse asparagine-linked complex type alpha-(2,3)-sialyloligosaccharides. In addition, two kinds of disialyloligosaccharides in which the sialyl linkage was a mixture of alpha-(2,3)- and alpha-(2,6)-types were also specifically prepared by an additional alpha-(2,6)-sialyltransferase reaction toward mono-alpha-(2,3)-sialyloligosaccharides thus obtained.
Fukae
Kazuhiro
K
Otsuka Chemical Co., Ltd. 463, Kagasuno, Kawauchicho, Tokushima, 771-0193, Japan.
Yamamoto
Naoki
N
Hatakeyama
Yuri
Y
Kajihara
Yasuhiro
Y
D000818:Animals; D001216:Asparagine / Q000737:chemistry*; D002236:Carbohydrate Conformation; D002851:Chromatography, High Pressure Liquid; D006026:Glycoside Hydrolases / Q000378:metabolism; D009345:Neisseria meningitidis / Q000201:enzymology; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D051381:Rats; D011994:Recombinant Proteins; D012799:Sialyltransferases / Q000378:metabolism*; D000094663:beta-Galactoside alpha-2,3-Sialyltransferase
D009844:Oligosaccharides; D011994:Recombinant Proteins; C016735:sialooligosaccharides; D001216:Asparagine; D012799:Sialyltransferases; D006026:Glycoside Hydrolases; D000094663:beta-Galactoside alpha-2,3-Sialyltransferase