Journal
TETRAHEDRON
Volume 66, Issue 39, Pages 7850-7855Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2010.07.036
Keywords
Glycosylation; Regioselective 3,4-benzylidene opening; Glycoconjugates; Helicobacter pylori; Carbohydrate synthesis
Categories
Funding
- Swedish Research Council
- The Royal Society [RG081255]
- European Commission [MRTN-CT-2004-005645 GlycoGold]
- Science Foundation Ireland [08/IN.1/82067]
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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 alpha-L-fucopyranosyl-(1 -> 2)-beta-D-galactopyranosyl-(1 3)-[alpha-L-fucopyranosyl-(1 -> 4)]-2-acetamido-2-deoxy-beta-D-glucopyranosyl-(1 -> 3)-beta-D-galactopyranoside, is presented to enable further investigation of the carbohydrate recognition process of H. pylori. (C) 2010 Elsevier Ltd. All rights reserved.
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