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  • Title: Synthesis of a common tetrasaccharide motif of Haemophilus influenzae LPS inner core structures.
    Author: Mannerstedt K, Segerstedt E, Olsson J, Oscarson S.
    Journal: Org Biomol Chem; 2008 Mar 21; 6(6):1087-91. PubMed ID: 18327335.
    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.
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