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Synthesis of the Lewis b pentasaccharide and a HSA-conjugate thereof
Univ Bangor, Sch Chem, Bangor LL57 2UW, Gwynedd, Wales..
Univ Stockholm, Arrhenius Lab, Dept Organ Chem, S-10691 Stockholm, Sweden..
Univ Stockholm, Arrhenius Lab, Dept Organ Chem, S-10691 Stockholm, Sweden..
Univ Coll Dublin, Ctr Synth & Chem Biol, Dublin 4, Ireland..ORCID iD: 0000-0002-8273-4918
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2010 (English)In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 66, no 39, p. 7850-7855Article in journal (Refereed) Published
Abstract [en]

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.

Place, publisher, year, edition, pages
Elsevier BV , 2010. Vol. 66, no 39, p. 7850-7855
Keywords [en]
Glycosylation, Regioselective 3, 4-benzylidene opening, Glycoconjugates, Helicobacter pylori, Carbohydrate synthesis
National Category
Biochemistry Molecular Biology
Identifiers
URN: urn:nbn:se:kth:diva-305707DOI: 10.1016/j.tet.2010.07.036ISI: 000282071100020Scopus ID: 2-s2.0-77956394017OAI: oai:DiVA.org:kth-305707DiVA, id: diva2:1617230
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QC 20211206

Available from: 2021-12-06 Created: 2021-12-06 Last updated: 2025-02-20Bibliographically approved

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Lahmann, Martina

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