Synthesis of specifically monofluorinated ligands related to the O-polysaccharide of Shigella dysenteriae type 1.
The synthesis is reported of galactopyranose nucleophiles monofluorinated at positions 3, 4, or 6 and protected by 4,6-O-benzylidene, 3,6-di-O-benzyl, or 3,4-O-isopropylidene groups, respectively. The condensation of these nucleophiles with 2,3,4-tri-O-benzoyl-alpha-L-rhamnosyl bromide gave, after deprotection, the disaccharide analogues of methyl O-alpha-L-rhamnopyranosyl-(1-->2)-alpha-D-galactopyranoside, monofluorinated at position 3, 4, or 6 of the galactoside residue.
Mulard
L A
LA
NIDDK, National Institutes of Health, Bethesda, Maryland 20892.
Kovác
P
P
Glaudemans
C P
CP
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D005459:Fluorides; D005461:Fluorine; D005690:Galactose; D007202:Indicators and Reagents; D008024:Ligands; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D019081:O Antigens; D009904:Optical Rotation; D011135:Polysaccharides, Bacterial / Q000737:chemistry*; D012210:Rhamnose; D012762:Shigella dysenteriae / Q000737:chemistry* / Q000276:immunology
D004187:Disaccharides; D007202:Indicators and Reagents; D008024:Ligands; D019081:O Antigens; D011135:Polysaccharides, Bacterial; D005461:Fluorine; D005459:Fluorides; D012210:Rhamnose; D005690:Galactose