ArticleThe Journal of organic chemistry2014
Iminosugar C-glycoside analogues of α-D-GlcNAc-1-phosphate: synthesis and bacterial transglycosylase inhibition.
Article in The Journal of organic chemistry, 2014. 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.
- Synthesis and Evaluation of Iminosugar-Based Analogs of UDP-GlcNAc as Putative OGT Inhibitors.ChemMedChem · 2026Article
- Ring opening, conformational analysis and NagZ inhibition of a GlcNAc-configured iminosugar-derived aziridine.Carbohydrate research · 2026Article
- Structural and mechanistic studies of the N-glycosylation machinery: from lipid-linked oligosaccharide biosynthesis to glycan transfer.Glycobiology · 2023Review
- Article
- Synthesis of modified 1,5-imino-d-xylitols as ligands for lysosomalMonatshefte fur chemie · 2019Article
- Towards new antibiotics targeting bacterial transglycosylase: Synthesis of a Lipid II analog as stable transition-state mimic inhibitor.Bioorganic & medicinal chemistry letters · 2018Article
- Structural basis of the molecular ruler mechanism of a bacterial glycosyltransferase.Nature communications · 2018Article
- Glycosyltransferases and Transpeptidases/Penicillin-Binding Proteins: Valuable Targets for New Antibacterials.Antibiotics (Basel, Switzerland) · 2016Review
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Authors and funding
9 authors.
Funding
Abstract
We herein describe the first synthesis of iminosugar C-glycosides of α-D-GlcNAc-1-phosphate in 10 steps starting from unprotected D-GlcNAc. A diastereoselective intramolecular iodoamination-cyclization as the key step was employed to construct the central piperidine ring of the iminosugar and the C-glycosidic structure of α-D-GlcNAc. Finally, the iminosugar phosphonate and its elongated phosphate analogue were accessed. These phosphorus-containing iminosugars were coupled efficiently with lipophilic monophosphates to give lipid-linked pyrophosphate derivatives, which are lipid II mimetics endowed with potent inhibitory properties toward bacterial transglycosylases (TGase).
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