ArticleBeilstein journal of organic chemistry2016
Automated glycan assembly of a S. pneumoniae serotype 3 CPS antigen.
Article in Beilstein journal of organic chemistry, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed.
- Expediting Glycospace Exploration: Therapeutic Glycans via Automated Synthesis.Angewandte Chemie (International ed. in English) · 2025Review
- The effect of neighbouring group participation and possible long range remote group participation inBeilstein journal of organic chemistry · 2025Review
- Synthetic BSA-conjugated disaccharide related to theFrontiers in immunology · 2024Article
- Semi- and fully synthetic carbohydrate vaccines against pathogenic bacteria: recent developments.Biochemical Society transactions · 2021Review
- Nanovesicles displaying functional linear and branched oligomannose self-assembled from sequence-defined Janus glycodendrimers.Proceedings of the National Academy of Sciences of the United States of America · 2020Article
- Traceless Photolabile Linker Expedites the Chemical Synthesis of Complex Oligosaccharides by Automated Glycan Assembly.Journal of the American Chemical Society · 2019Article
- Automated Glycan Assembly: A Perspective.Journal of the American Chemical Society · 2019Article
- A Semi-synthetic Oligosaccharide Conjugate Vaccine Candidate Confers Protection against Streptococcus pneumoniae Serotype 3 Infection.Cell chemical biology · 2016Article
Corrections and comments
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Authors and funding
6 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Vaccines against S. pneumoniae, one of the most prevalent bacterial infections causing severe disease, rely on isolated capsular polysaccharide (CPS) that are conjugated to proteins. Such isolates contain a heterogeneous oligosaccharide mixture of different chain lengths and frame shifts. Access to defined synthetic S. pneumoniae CPS structures is desirable. Known syntheses of S. pneumoniae serotype 3 CPS rely on a time-consuming and low-yielding late-stage oxidation step, or use disaccharide building blocks which limits variability. Herein, we report the first iterative automated glycan assembly (AGA) of a conjugation-ready S. pneumoniae serotype 3 CPS trisaccharide. This oligosaccharide was assembled using a novel glucuronic acid building block to circumvent the need for a late-stage oxidation. The introduction of a washing step with the activator prior to each glycosylation cycle greatly increased the yields by neutralizing any residual base from deprotection steps in the synthetic cycle. This process improvement is applicable to AGA of many other oligosaccharides.
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