ArticleACS chemical biology2016
Development of Rare Bacterial Monosaccharide Analogs for Metabolic Glycan Labeling in Pathogenic Bacteria.
Article in ACS chemical biology, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 31 papers.
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Who cites it
31 citing papers in PubMed, 65 citations in OpenAlex.
- Development of Fluorogenic Probes to Detect Glycan-Degrading Enzymes in Bacteria.ACS infectious diseases · 2026Article
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- Examination of Acetylated Monosaccharides as Metabolic Probes in Bacteria.ACS infectious diseases · 2025Article
- Discovering microbiota functions via chemical probe incorporation for targeted sequencing.Current opinion in chemical biology · 2025Review
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- Metabolic Usage and Glycan Destinations of GlcNAz inACS chemical biology · 2024Article
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- Thioglycosides Act as Metabolic Inhibitors of Bacterial Glycan Biosynthesis.ACS infectious diseases · 2023Article
- Preference of Bacterial Rhamnosyltransferases for 6-Deoxysugars Reveals a Strategy To Deplete O-Antigens.Journal of the American Chemical Society · 2023Article
- Scalable Synthesis of Versatile Rare Deoxyamino Sugar Building Blocks from d-Glucosamine.The Journal of organic chemistry · 2023Article
- Shedding Light on Bacterial Physiology with Click Chemistry.Israel journal of chemistry · 2023Article
- Chemical tools to study bacterial glycans: a tale from discovery of glycoproteins to disruption of their function.Israel journal of chemistry · 2023Article
- Selective Exoenzymatic Labeling of Lipooligosaccharides of Neisseria gonorrhoeae with α2,6-Sialoside Analogues.Chembiochem : a European journal of chemical biology · 2022Article
- Recent Progress in Identifying Bacteria with Fluorescent Probes.Molecules (Basel, Switzerland) · 2022Review
- Synthesis and Application of Rare Deoxy Amino l-Sugar Analogues to Probe Glycans in Pathogenic Bacteria.ACS infectious diseases · 2022Article
- Sweet impersonators: Molecular mimicry of host glycans by bacteria.Glycobiology · 2022Review
- Chemical Reporters for Bacterial Glycans: Development and Applications.Chemical reviews · 2022Review
- Facile and Scalable Route to Access Rare Deoxy Amino Sugars for Nonulosonic Acid Aldolase Biosynthesis.Frontiers in chemistry · 2022Article
- Metabolic Labeling of Legionaminic Acid in Flagellin Glycosylation of Campylobacter jejuni Identifies Maf4 as a Putative Legionaminyl Transferase.Angewandte Chemie (International ed. in English) · 2021Article
- ProtectedACS chemical biology · 2021Article
Corrections and comments
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Authors and funding
7 authors at 2 institutions in 2 countries.
Funding
Abstract
Bacterial glycans contain rare, exclusively bacterial monosaccharides that are frequently linked to pathogenesis and essentially absent from human cells. Therefore, bacterial glycans are intriguing molecular targets. However, systematic discovery of bacterial glycoproteins is hampered by the presence of rare deoxy amino sugars, which are refractory to traditional glycan-binding reagents. Thus, the development of chemical tools that label bacterial glycans is a crucial step toward discovering and targeting these biomolecules. Here, we explore the extent to which metabolic glycan labeling facilitates the studying and targeting of glycoproteins in a range of pathogenic and symbiotic bacterial strains. We began with an azide-containing analog of the naturally abundant monosaccharide N-acetylglucosamine and discovered that it is not broadly incorporated into bacterial glycans, thus revealing a need for additional azidosugar substrates to broaden the utility of metabolic glycan labeling in bacteria. Therefore, we designed and synthesized analogs of the rare deoxy amino d-sugars N-acetylfucosamine, bacillosamine, and 2,4-diacetamido-2,4,6-trideoxygalactose and established that these analogs are differentially incorporated into glycan-containing structures in a range of pathogenic and symbiotic bacterial species. Further application of these analogs will refine our knowledge of the glycan repertoire in diverse bacteria and may find utility in treating a variety of infectious diseases with selectivity.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.