title: Synthesis of a common tetrasaccharide motif of Haemophilus influenzae LPS inner core structures.
abstract: A conserved tetrasaccharide structure, L-glycero-alpha-D-manno-heptopyranosyl-(1-->2)-(6-O-aminoethylphosphono-L-glycero-alpha-D-manno-heptopyranosyl)-(1-->3)-[beta-D-glucopyranosyl-(1-->4)]-L-glycero-alpha-D-manno-heptopyranose, from the LPS inner core of Haemophilus influenzae has been synthesised as its ethylamino glycosides to allow later conjugations. Starting from a previously synthesised suitably protected trisaccharide intermediate, the third heptose and subsequently the spacer were introduced using thioglycoside donor chemistry. The phosphoethanolamine was formed employing a Boc-protected phosphoamidite. Final deprotection and conjugation to biotin gave conjugates that will be used to study the specificity of MAbs raised against native LPS structures.
authors.affiliation: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, S-10691 Stockholm, Sweden.
authors.forename: Karin
authors.initials: K
authors.lastname: Mannerstedt
authors.forename: Eva
authors.initials: E
authors.lastname: Segerstedt
authors.forename: Johan
authors.initials: J
authors.lastname: Olsson
authors.forename: Stefan
authors.initials: S
authors.lastname: Oscarson
mesh_terms: D001710:Biotin / Q000737:chemistry; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D006193:Haemophilus influenzae / Q000737:chemistry*; D008070:Lipopolysaccharides / Q000737:chemistry*; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D008070:Lipopolysaccharides; D009844:Oligosaccharides; D001710:Biotin