ArticleJournal of the American Chemical Society2012
Chemical synthesis and immunological evaluation of the inner core oligosaccharide of Francisella tularensis.
Article in Journal of the American Chemical Society, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 19 papers.
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Who cites it
19 citing papers in PubMed.
- Synthesis of disaccharide and trisaccharide substructures of an A. baumannii lipooligosaccharide core.Carbohydrate research · 2025Article
- A Bioactive Synthetic Outer-Core Oligosaccharide Derived from a Klebsiella pneumonia Lipopolysaccharide for Bacteria Recognition.Chemistry (Weinheim an der Bergstrasse, Germany) · 2023Article
- Total Synthesis of a PentasaccharideEuropean journal of organic chemistry · 2022Article
- Total synthesis ofChemical science · 2022Article
- Chemoenzymatic Synthesis ofJournal of the American Chemical Society · 2020Article
- Glycoconjugate vaccine using a genetically modified O antigen induces protective antibodies toProceedings of the National Academy of Sciences of the United States of America · 2019Article
- Potential targets for next generation antimicrobial glycoconjugate vaccines.FEMS microbiology reviews · 2018Review
- Synthesis of a Pentasaccharide Fragment Related to the Inner Core Region of Rhizobial and Agrobacterial Lipopolysaccharides.The Journal of organic chemistry · 2017Article
- Enzymatic synthesis of 3-deoxy-d-manno-octulosonic acid (KDO) and its application for LPS assembly.Bioorganic & medicinal chemistry letters · 2016Article
- An antibacterial vaccination strategy based on a glycoconjugate containing the core lipopolysaccharide tetrasaccharide Hep2Kdo2.Nature chemistry · 2016Article
- Antibacterials: A sweet vaccine.Nature chemistry · 2016Article
- Scope and Limitations of 3-Iodo-Kdo Fluoride-Based Glycosylation Chemistry using N-Acetyl Glucosamine Acceptors.ChemistryOpen · 2015Article
- Assembly of a Complex Branched Oligosaccharide by Combining Fluorous-Supported Synthesis and Stereoselective Glycosylations using Anomeric Sulfonium Ions.Chemistry (Weinheim an der Bergstrasse, Germany) · 2015Article
- Chemical synthesis of the outer core oligosaccharide of Escherichia coli R3 and immunological evaluation.Organic & biomolecular chemistry · 2015Article
- First and stereoselective synthesis of an α-(2→5)-linked disaccharide of 3-deoxy-D-manno-oct-2-ulosonic acid (Kdo).Organic letters · 2015Article
- Synthesis of chlamydia lipopolysaccharide haptens through the use of α-specific 3-iodo-Kdo fluoride glycosyl donors.Chemistry (Weinheim an der Bergstrasse, Germany) · 2015Article
- Development of αGlcN(1↔1)αMan-based lipid A mimetics as a novel class of potent Toll-like receptor 4 agonists.Journal of medicinal chemistry · 2014Article
- The atypical lipopolysaccharide of Francisella.Carbohydrate research · 2013Review
- Synthetically defined glycoprotein vaccines: current status and future directions.Chemical science · 2013Article
Corrections and comments
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Authors and funding
6 authors.
Funding
Abstract
Francisella tularensis, which is a Gram negative bacterium that causes tularemia, has been classified by the Center for Disease Control and Prevention (CDC) as a category A bioweapon. The development of vaccines, immunotherapeutics, and diagnostics for F. tularensis requires a detailed knowledge of the saccharide structures that can be recognized by protective antibodies. We have synthesized the inner core region of the lipopolysaccharide (LPS) of F. tularensis to probe antigenic responses elicited by a live and subunit vaccine. The successful preparation of the target compound relied on the use of a disaccharide which was modified by the orthogonal protecting groups diethylisopropylsilyl (DEIPS), 2-naphthylmethyl (Nap), allyl ether (All), and levulinoyl (Lev) ester. The ability to remove the protecting groups in different orders made it possible to establish the optimal glycosylations sequence to prepare a highly crowded 1,2,3-cis configured branching point. A variety of different methods were exploited to control anomeric selectivities of the glycosylations. A comparison of the (1)H NMR spectra of isolated material and the synthetic derivative confirmed the reported structural assignment of the inner core oligosaccharide of F. tularensis . The observation that immunizations with LPS lead to antibody responses to the inner core saccharides provides an impetus to further explore this compound as a vaccine candidate.
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