Synthesis and evaluation of 5-thio-L-fucose-containing oligosaccharide.
5-Thio-L-fucose-containing trisaccharide H-type II was synthesized. The 3',4'-O-isopropylidene-2-azido-2-deoxylactoside derivative, which was prepared from lactose by azidonitration of lactal, was used as a starting material. By regio- and stereoselective 5-thio-L-fucosylation of the 6,6'-dibenzoate 5 with 5-thiofucosyl trichloroacetimidate 6 and subsequent deprotection gave the 5-thio-L-fucose-containing H-type II 1. Conformational analysis of the 5-thio-L-fucose-containing H-type II and the native H-type II was carried out through NOESY experiments. The observed NOE values between N-acetylglucosamine and galactose, and galactose and fucose were same for these two trisaccharides. However, NOE values between fucose and N-acetylglucosamine were significantly different. Binding of the 5-thio-L-fucose-containing H-type II to lectins and antibodies were in some case stronger and in some case weaker than those of the native trisaccharide.
Izumi
Masayuki
M
Department of Life Science, Graduate school of Bioscience and Biotechnology, Tokyo Institute of Technology, 4259 Nagatsuta, Yokohama 226-8501, Japan.masayuki.izumi@aist.go.jp
Tsuruta
Osamu
O
Kajihara
Yasuhiro
Y
Yazawa
Shin
S
Yuasa
Hideya
H
Hashimoto
Hironobu
H
D002240:Carbohydrate Sequence; D005643:Fucose / Q000031:analogs & derivatives* / Q000737:chemistry; D006384:Hemagglutination / Q000276:immunology; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D009844:Oligosaccharides / Q000138:chemical synthesis / Q000737:chemistry* / Q000276:immunology
C119490:5-thiofucose; D009844:Oligosaccharides; D005643:Fucose