Synthesis of a tetrasaccharide donor corresponding to the O-specific polysaccharide of Shigella dysenteriae type 1 |
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| Authors: | Vince Pozsgay Cornelis P.J. Glaudemans John B. Robbins Rachel Schneerson |
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| Affiliation: | 1. Laboratory of Developmental and Molecular Immunity, National Institute of Child Health and Human Development, Bethesda, MD 20892 USA;2. Laboratory of Medicinal Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, Bethesda, MD 20892 USA |
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| Abstract: | O-(2,4-Di-O-chloroacetyl-α-l-rhamnopyranosyl)-(1 → 2)-O-(3,4,6-tri-O-benzoyl-α-d-galactopyranosyl)-(1 → 3)-O-(2-acetamido-4,6-di-O-acetyl-2-deoxy-α-d-glycopyranosyl)-(1 → 3)-2,4-di-O-benzoyl-α-l-rhamnopyranosyl trichloroacetimidate (1) was synthesized in a stepwise manner, using the following monosaccharide units: 2-(trimethylsilyl)ethyl 2,4-di-O-benzoyl-α-l-rhamnopyranoside, 2-azido-4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-β-d-glycopyranosyl chloride, methyl 3,4,6-tri-O-benzoyl-2-O-(4-methoxybenzyl)-1-thio-β-d-galactopyranoside, and 2,4-di-O-benzoyl-3-O-chloroacetyl-α-l-rhamnopyranosyl chloride. Compound 1 corresponds to a complete tetrasaccharide repeating unit of the O-specific polysaccharide of the lipopolysaccharide of Shigella dysenteriae type 1. |
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| Keywords: | Corresponding author. Mailing address: NIH Building 6 Rm. 145 Bethesda MD 20892 USA. |
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