ArticleAngewandte Chemie (International ed. in English)2023
Synthetic Zwitterionic Streptococcus pneumoniae Type 1 Oligosaccharides Carrying Labile O-Acetyl Esters.
Article in Angewandte Chemie (International ed. in English), 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed, 11 citations in OpenAlex.
- Total synthesis of zwitterionic PS A2 oligosaccharides fromScience advances · 2025Article
- Total Synthesis and Anomeric Configuration Revision of Zwitterionic Polysaccharide A2's Pentasaccharide Repeating Unit fromJACS Au · 2025Article
- Synthesis, Conformal Analysis, and Antibody Binding of Staphylococcus aureus Capsular Polysaccharide Type 5 Oligosaccharides.Angewandte Chemie (International ed. in English) · 2025Article
- Controlling Glycan Folding with Ionic Functional Groups.Journal of the American Chemical Society · 2025Article
- Long, SyntheticJournal of the American Chemical Society · 2025Article
- Total Synthesis and Structural Studies of ZwitterionicJournal of the American Chemical Society · 2023Article
- Synthetic Zwitterionic Streptococcus pneumoniae Type 1 Oligosaccharides Carrying Labile O-Acetyl Esters.Angewandte Chemie (International ed. in English) · 2023Article
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Authors and funding
8 authors at 4 institutions in 4 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
We herein report the first total synthesis of the Streptococcus pneumoniae serotype 1 (Sp1) oligosaccharide, a unique zwitterionic capsular polysaccharide carrying labile O-acetyl esters. The target oligosaccharides, featuring rare α-2,4-diamino-2,4,6-trideoxy galactose (AAT) and α-galacturonic acids, were assembled up to the 9-mer level, in a highly stereoselective manner using trisaccharide building blocks. The lability of the O-acetyl esters imposed a careful deprotection scheme to prevent migration and hydrolysis. The migration was investigated in detail at various pD values using NMR spectroscopy, to show that migration and hydrolysis of the C-3-O-acetyl esters readily takes place under neutral conditions. Structural investigation showed the oligomers to adopt a right-handed helical structure with the acetyl esters exposed on the periphery of the helix in close proximity of the neighboring AAT residues, thereby imposing conformational restrictions on the AATα1-4GalA(3OAc) glycosidic linkages, supporting the helical shape of the polysaccharide, that has been proposed to be critical for its unique biological activity.
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