ArticleChemistry (Weinheim an der Bergstrasse, Germany)2021
Azide-Functionalized Derivatives of the Virulence-Associated Sugar Pseudaminic Acid: Chiral Pool Synthesis and Labeling of Bacteria.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2021. 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, 16 citations in OpenAlex.
- Distinct Microbiota and Functional Pathway Profiles Define Success and Failure in Regenerative Endodontic Treatment.International endodontic journal · 2026Observational
- Engineered bacteria and bacteria-derived nanomaterials for cancer therapy: Mechanisms, designs and advances.Bioactive materials · 2026Review
- Chemical biology tools to probe bacterial glycans.Current opinion in chemical biology · 2024Review
- Chemical tools to study bacterial glycans: a tale from discovery of glycoproteins to disruption of their function.Israel journal of chemistry · 2023Article
- Recent Progress in Identifying Bacteria with Fluorescent Probes.Molecules (Basel, Switzerland) · 2022Review
- Syntheses of Legionaminic Acid, Pseudaminic Acid, Acetaminic Acid, 8-Organic letters · 2022Article
- Synthesis and Application of Rare Deoxy Amino l-Sugar Analogues to Probe Glycans in Pathogenic Bacteria.ACS infectious diseases · 2022Article
- Azide-Functionalized Derivatives of the Virulence-Associated Sugar Pseudaminic Acid: Chiral Pool Synthesis and Labeling of Bacteria.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
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Authors and funding
6 authors at 2 institutions in 3 countries.
Funding
Abstract
Pseudaminic acid (Pse) is a significant prokaryotic monosaccharide found in important Gram-negative and Gram-positive bacteria. This unique sugar serves as a component of cell-surface-associated glycans or glycoproteins and is associated with their virulence. We report the synthesis of azidoacetamido-functionalized Pse derivatives as part of a search for Pse-derived metabolic labeling reagents. The synthesis was initiated with d-glucose (Glc), which served as a cost-effective chiral pool starting material. Key synthetic steps involve the conversion of C1 of Glc into the terminal methyl group of Pse, and inverting deoxyaminations at C3 and C5 of Glc followed by backbone elongation with a three-carbon unit using the Barbier reaction. Metabolic labeling experiments revealed that, of the four Pse derivatives, ester-protected C5 azidoacetamido-Pse successfully labeled cells of Pse-expressing Gram-positive and Gram-negative strains. No labeling was observed in cells of non-Pse-expressing strains. The ester-protected and C5 azidoacetamido-functionalized Pse is thus a useful reagent for the identification of bacteria expressing this unique virulence-associated nonulosonic acid.
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