Synthesis of an unnatural N-glycan-linked dolichyl pyrophosphate precursor.
An unnatural alpha-D-mannopyranose-linked chitobiosyl dolichyl pyrophosphate, a stereoisomer of the N-glycan biosynthesis intermediate, was synthesized. The protected trisaccharide, alpha-D-Man-(1-->4)-beta-D-GlcNAc-(1-->4)-D-GlcNAc, carrying a 4-methylbenzoyl group was prepared for the convenience of a TLC analysis. 1-O-Phosphorylation, condensation with dolichyl phosphate, and subsequent deprotection afforded the title compound.
Nakahara
Yuko
Y
Institute of Glycotechnology, Department of Applied Biochemistry, Tokai University, Kitakaname 1117, Hiratsuka, Kanagawa 259-1292, Japan.
Nonaka
Tomoharu
T
Hojo
Hironobu
H
Nakahara
Yoshiaki
Y
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D002855:Chromatography, Thin Layer; D004288:Dolichol Phosphates / Q000138:chemical synthesis* / Q000737:chemistry; D008358:Mannose / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D008969:Molecular Sequence Data; D010766:Phosphorylation; D014312:Trisaccharides / Q000737:chemistry
D004288:Dolichol Phosphates; D014312:Trisaccharides; C026406:dolichol pyrophosphate; D008358:Mannose