Beilstein J. Org. Chem.2010,6, 704–708, doi:10.3762/bjoc.6.80
-containing lactose derivative a suitably protected lacto-N-neotetraose tetrasaccharide structure was constructed through subsequential couplings with two thioglycoside donors, a glucosamine residue followed by a galactose derivative, using NIS/AgOTf as promoter. Removal of a silyl protecting group at the
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Conclusion: An effective synthesis of a biologically interesting pentasaccharide structure has been accomplished. The target pentasaccharide, an α-GalNAc substituted lacto-N-neotetraose structure, comprises a phosphoethanolamine motif and a spacer aglycon. Through the spacer, biotin and protein conjugates of
the title compound have been constructed to allow further use in biological experiments.
Keywords: conjugate vaccines; glycoconjugates; Haemophilus influenzae; lacto-N-neotetraose; oligosaccharide synthesis; thioglycosides; Introduction
Haemophilus influenzae are Gram-negative bacteria divided into
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Graphical Abstract
Figure 1:
The H. influenzae outer core target structure.