Systematic synthesis of N-methyl-1-deoxynojirimycin-containing, Le(x), Le(a), sialyl-Le(x) and sialyl-Le(a) epitopes recognized by selectins.
A systematic synthesis of the N-methyl-1-deoxynojirimycin-containing oligosaccharides related to the Lewis x, Lewis a, sialyl-Lewis x and sialyl-Lewis a antigens has been achieved. The couplings of the suitably protected 1-deoxynojirimycin derivative 10 with methyl-1-thioglycosides (glycosyl donors) of L-fucose (11), D-galactose (15) and alpha-sialyl-(2-->3)-D-galactose (27) were carried out by using dimethyl(methylthio)sulfonium triflate (DMTST) or N-iodosuccinimide/trifluoromethanesulfonic acid (NIS/TfOH) as the glycosyl promoter. The resulting di- and tri-saccharides were each converted, by further cross glycosylations with 11, 15 or 27, to the desired tri- and tetra-saccharides 3-6 that inhibit the recognition between sialyl-Lewis x and selectins, a family of leukocyte cell adhesion molecules.
Kiso
M
M
Department of Applied Bioorganic Chemistry, Gifu University, Japan.
Furui
H
H
Ando
K
K
Ishida
H
H
Hasegawa
A
A
D017485:1-Deoxynojirimycin / Q000031:analogs & derivatives* / Q000737:chemistry; D018395:CA-19-9 Antigen; D002240:Carbohydrate Sequence; D015815:Cell Adhesion Molecules / Q000378:metabolism*; D000939:Epitopes / Q000737:chemistry* / Q000276:immunology; D005732:Gangliosides / Q000138:chemical synthesis; D007983:Lewis Blood Group Antigens / Q000737:chemistry* / Q000276:immunology / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008969:Molecular Sequence Data; D015394:Molecular Structure; D009844:Oligosaccharides / Q000138:chemical synthesis / Q000737:chemistry; D000080506:Sialyl Lewis X Antigen
D018395:CA-19-9 Antigen; D015815:Cell Adhesion Molecules; D000939:Epitopes; D005732:Gangliosides; D007983:Lewis Blood Group Antigens; D009844:Oligosaccharides; D000080506:Sialyl Lewis X Antigen; C016735:sialooligosaccharides; D017485:1-Deoxynojirimycin; C064564:sialyl Le(a) ganglioside; C033424:N-methyldeoxynojirimycin