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Synthesis of the Lewis b pentasaccharide and a HSA-conjugate thereof |
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| Authors: | Viviane Fourniè re,Ferenc Sajtos,Martina Lahmann |
| Affiliation: | a The School of Chemistry, University of Bangor, Alun Roberts Building, Deiniol Road, Bangor, Gwynedd LL57 2UW, UK b Department of Organic Chemistry, Arrhenius Laboratory, University of Stockholm, S-106 91 Stockholm, Sweden c Centre for Synthesis and Chemical Biology, University College Dublin, Belfield, Dublin 4, Ireland |
| Abstract: | Helicobacter pylori, a gastric pathogen, binds to various blood group antigens, including the Lewis types, present in the gastric tissue and a relation between the presentation of the ligands and the overall strength of binding has been assumed. Synthetic Lewis b tetra- and hexasaccharide conjugates are available but not the analogous pentasaccharide. An efficient synthesis of the amino spacer equipped Lewis b pentasaccharide, 3-aminopropyl α-l-fucopyranosyl-(1→2)-β-d-galactopyranosyl-(1→3)-[α-l-fucopyranosyl-(1→4)]-2-acetamido-2-deoxy-β-d-glucopyranosyl-(1→3)-β-d-galactopyranoside, is presented to enable further investigation of the carbohydrate recognition process of H. pylori. |
| Keywords: | Glycosylation Regioselective 3,4-benzylidene opening Glycoconjugates Helicobacter pylori Carbohydrate synthesis |
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