Synthesis of 1,2,3-triazolyl analog of Neisseria meningitidis A capsular polysaccharide |
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Authors: | Madhuri Vangala Srinivas Hotha |
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Affiliation: | 1. Department of Chemistry, Indian Institute of Science Education and Research, Pune, Indiamadhurivangala99@gmail.com;3. Department of Chemistry, Indian Institute of Science Education and Research, Pune, India |
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Abstract: | AbstractTowards constructing a stable, non-hydrolyzable linkage for Neisseria meningitidis type A (MenA) polysaccharide, the phosphate bridge of its (1→6)-linked 2-acetamido-2-deoxy-α-D-mannopyranosyl phosphate repeating unit was replaced by a triazolyl analog using Cu(I) catalyzed click reaction. The synthesis involved anomeric azidation of N-acetyl-D-mannosamine derivative from its acetate precursor using stoichiometric amount of FeCl3 and one-pot synthesis of precursors for di- and tri- triazolyl saccharides with an azidoethyl spacer at the reducing end for bioconjugation. |
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Keywords: | Click chemistry N-acetyl D-mannosamine Neisseria meningitidis oligosaccharide |
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