Synthesis of L-glycero-D-manno-heptopyranose-containing oligosaccharide structures found in lipopolysaccharides from Haemophilus influenzae.
Syntheses are described of the tetrasaccharide 2-(4-trifluoroacetamidophenyl)ethyl O-(beta-D-galactopyranosyl)-(1-->2)-O- (L-glycero-alpha-D-manno-heptopyranosyl)-(1-->2)-O-(L-glycero-alpha-D- manno-heptopyranosyl)-(1-->3)-L-glycero-alpha-D-manno-heptopyranoside (20) and the three trisaccharides 2-(4-trifluoroacetamidophenyl)ethyl O-(L-glycero-alpha-D-manno-heptopyranosyl)-(1-->2)-O-(L-glycero-alpha-D- manno-heptopyranosyl)-(1-->3)-L-glycero-alpha-D-manno-heptopyranoside (17), 2-(4-trifluoroacetamidophenyl)ethyl O-(beta-D-glucopyranosyl)-(1-->4)- O-(beta-D-glucopyranosyl)-(1-->4)-L-glycero-alpha-D-manno-heptopyrano side (5), and 2-(4-trifluoro-acetamidophenyl)ethyl O-(beta-D-galactopyranosyl)-(1-->4)-O-(beta-D-glucopyranosyl)-(1-->4)- L-glycero-alpha-D-manno-heptopyranoside (8), corresponding to structures found in the lipooligosaccharides of Haemophilus influenzae.
Bernlind
C
C
Department of Organic Chemistry, Arrhenius Laboratory, University of Stockholm, Sweden.
Oscarson
S
S
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D006193:Haemophilus influenzae / Q000737:chemistry*; D006539:Heptoses / Q000032:analysis / Q000737:chemistry*; D008070:Lipopolysaccharides / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D015394:Molecular Structure; D009844:Oligosaccharides / Q000138:chemical synthesis*; D011135:Polysaccharides, Bacterial / Q000737:chemistry
D006539:Heptoses; D008070:Lipopolysaccharides; D009844:Oligosaccharides; D011135:Polysaccharides, Bacterial