ArticleACS chemical biology2017
Complete Tetrasaccharide Repeat Unit Biosynthesis of the Immunomodulatory Bacteroides fragilis Capsular Polysaccharide A.
Article in ACS chemical biology, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 26 papers.
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Who cites it
26 citing papers in PubMed, 38 citations in OpenAlex.
- Stepwise Assembly of theBiochemistry · 2026Article
- Proteome-wide bioinformatic annotation and functional validation of the monotopic phosphoglycosyl transferase superfamily.Proceedings of the National Academy of Sciences of the United States of America · 2024Article
- An exopolysaccharide pathway from a freshwaterJournal of bacteriology · 2024Article
- Proteome-Wide Bioinformatic Annotation and Functional Validation of the Monotopic Phosphoglycosyl Transferase Superfamily.bioRxiv : the preprint server for biology · 2024Article
- A novel exopolysaccharide pathway from a freshwaterbioRxiv : the preprint server for biology · 2023Article
- The biofilm community resurfaces: new findings and post-pandemic progress.Journal of bacteriology · 2023Review
- Molecular modelling and site-directed mutagenesis provide insight into saccharide pyruvylation by the Paenibacillus alvei CsaB enzyme.Scientific reports · 2023Article
- Identification of a second glycoform of the clinically prevalent O1 antigen fromProceedings of the National Academy of Sciences of the United States of America · 2023Article
- Chemoenzymatic Preparation of aACS omega · 2023Article
- Chemical Reporters for Bacterial Glycans: Development and Applications.Chemical reviews · 2022Review
- AssayingBiomolecules · 2021Article
- Identification of a Novel Pyruvyltransferase UsingJournal of bacteriology · 2021Article
- Lipopolysaccharide Is a 4-Aminoarabinose Donor to Exogenous Polyisoprenyl Phosphates through the Reverse Reaction of the Enzyme ArnT.ACS omega · 2021Article
- Metabolic regulation in the immune response to cancer.Cancer communications (London, England) · 2021Review
- Dismantling the bacterial glycocalyx: Chemical tools to probe, perturb, and image bacterial glycans.Bioorganic & medicinal chemistry · 2021Review
- Making the Enterobacterial Common Antigen Glycan and Measuring Its Substrate Sequestration.ACS chemical biology · 2021Article
- Exploring the Gut-Brain Axis for the Control of CNS Inflammatory Demyelination: Immunomodulation byFrontiers in immunology · 2021Review
- General Utilization of Fluorescent Polyisoprenoids with Sugar Selective Phosphoglycosyltransferases.Biochemistry · 2020Article
- Metabolic inhibitors of bacterial glycan biosynthesis.Chemical science · 2020Article
- Pyruvate Substitutions on Glycoconjugates.International journal of molecular sciences · 2019Review
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
Capsular polysaccharide A (CPSA) is a four-sugar repeating unit polymer found on the surface of the gut symbiont Bacteroides fragilis that has therapeutic potential in animal models of autoimmune disorders. This therapeutic potential has been credited to its zwitterionic character derived from a positively charged N-acetyl-4-aminogalactosamine (AADGal) and a negatively charged 4,6-O-pyruvylated galactose (PyrGal). In this report, using a fluorescent polyisoprenoid chemical probe, the complete enzymatic assembly of the CPSA tetrasaccharide repeat unit is achieved. The proposed pyruvyltransferase, WcfO; galactopyranose mutase, WcfM; and glycosyltransferases, WcfP and WcfN, encoded by the CPSA biosynthesis gene cluster were heterologously expressed and functionally characterized. Pyruvate modification, catalyzed by WcfO, was found to occur on galactose of the polyisoprenoid-linked disaccharide (AADGal-Gal), and did not occur on galactose linked to uridine diphosphate (UDP) or a set of nitrophenyl-galactose analogues. This pyruvate modification was also found to be required for the incorporation of the next sugar in the pathway N-acetylgalactosamine (GalNAc) by the glycosyltransferase WcfP. The pyruvate acetal modification of a galactose has not been previously explored in the context of a polysaccharide biosynthesis pathway, and this work demonstrates the importance of this modification to repeat unit assembly. Upon production of the polyisoprenoid-linked AADGal-PyrGal-GalNAc, the proteins WcfM and WcfN were found to work in concert to form the final tetrasaccharide, where WcfM formed UDP-galactofuranose (Galf) and WcfN transfers Galf to the AADGal-PyrGal-GalNAc. This work demonstrates the first enzymatic assembly of the tetrasaccharide repeat unit of CPSA in a sequential single pot reaction.
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