Synthesis of colitose-containing oligosaccharide structures found in polysaccharides from Vibrio cholerae O139 synonym Bengal using thioglycoside donors.
The syntheses of the two colitose-containing trisaccharides 8-methoxycarbonyloctyl (3,6-dideoxy-alpha-L-xylo-hexopyranosyl)-(1-->2)-beta-D-galactopyranosyl -(1-->3)-2-acetamido-2-deoxy-beta-D-glucopyranoside and 8-methoxycarbonyloctyl beta-D-galactopyranosyl-(1-->3)-[(3,6- dideoxy-alpha-L-xylo-hexopyranosyl)-(1-->4)]-2-acetamido-2-deoxy-beta-D- glucopyranoside, and tetrasaccharide 8-methoxycarbonyloctyl (3,6-dideoxy-alpha-L-xylo-hexopyranosyl)-(1-->2)-beta-D-galactopyranosyl - (1-->3)-[(3,6-dideoxy-alpha-L-xylo-hexopyranosyl)-(1-->4)]-2-acetamido-2 -deoxy- beta-D-glucopyranoside are described. The oligosaccharides correspond to structures found in the capsular polysaccharide and the lipopolysaccharide of Vibrio cholerae O139 and also to lipopolysaccharide structures of E. coli O55 and Salmonella greenside. The colitose residues were introduced via dimethyl(methylthio)sulfonium trifluoromethanesulfonate promoted glycosylations using colitose thioglycosides as glycosyl donors.
Oscarson
S
S
Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Sweden.
Tedebark
U
U
Turek
D
D
D016667:Bacterial Capsules / Q000737:chemistry*; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D003837:Deoxy Sugars / Q000737:chemistry*; D004926:Escherichia coli / Q000737:chemistry; D005960:Glucosides / Q000138:chemical synthesis; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D015394:Molecular Structure; D013865:Thioglycosides / Q000737:chemistry*; D014312:Trisaccharides / Q000138:chemical synthesis*; D014734:Vibrio cholerae / Q000737:chemistry*
D003837:Deoxy Sugars; D005960:Glucosides; D013865:Thioglycosides; D014312:Trisaccharides; C025141:colitose