Affinity of 5-thio-L-fucose-containing Lewis X (LeX) trisaccharide analogs to anti-LeX monoclonal antibody.
5-Thiofucose-containing LeX trisaccharide analogs Gal beta(1,4)[5SFuc alpha(1,3)]GlcNAc-OMe (2) and Gal beta(1,4)[5SFuc beta(1,3)]GlcNAc-OMe (4) were synthesized via 5-thiofucosylation of methyl 2-azido-lactoside derivative 6 by the trichloroacetimidate method. Inhibitory activity of these analogs for the binding of LeX to anti-Lex antibody was evaluated by enzyme immunoassay, indicating that anti-LeX strictly recognizes alpha-configuration of the fucose moiety and its binding pocket includes no advantageous region, such as hydrophobic area, for recognizing the ring sulfur atom of 5-thiofucosyl LeX analog 2.
Tsuruta
O
O
Department of Life Science, Faculty of Bioscience and Biotechnology, Tokyo Institute of Technology, Yokohama, Japan.
Yuasa
H
H
Hashimoto
H
H
Kurono
S
S
Yazawa
S
S
D000911:Antibodies, Monoclonal / Q000276:immunology*; D002240:Carbohydrate Sequence; D005643:Fucose / Q000031:analogs & derivatives* / Q000737:chemistry; D007124:Immunoenzyme Techniques; D016256:Lewis X Antigen / Q000737:chemistry*; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000737:chemistry* / Q000276:immunology; D014312:Trisaccharides / Q000737:chemistry* / Q000276:immunology
C119490:5-thiofucose; D000911:Antibodies, Monoclonal; D016256:Lewis X Antigen; D009844:Oligosaccharides; D014312:Trisaccharides; C119491:methyl galactopyranosyl-1-4-(5-thiofucopyranosyl)(1-3)-N-acetylglucopyranoside; D005643:Fucose