ArticleAngewandte Chemie (International ed. in English)2014
Synthesis and structural characterization of three unique Helicobacter pylori α-cholesteryl phosphatidyl glucosides.
Article in Angewandte Chemie (International ed. in English), 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
What it found
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
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Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
5 citing papers in PubMed.
- Sterol-lipids enable large-scale, liquid-liquid phase separation in bilayer membranes of only two components.Proceedings of the National Academy of Sciences of the United States of America · 2024Article
- Step-economy synthesis of β-steryl sialosides using a sialyl iodide donor.The Journal of antibiotics · 2019Article
- Cholesterol lipids and cholesterol-containing lipid rafts in bacteria.Chemistry and physics of lipids · 2016Review
- Metabolic labelling of cholesteryl glucosides inChemical science · 2016Article
- Synthesis of cholesteryl-α-D-lactoside via generation and trapping of a stable β-lactosyl iodide.Tetrahedron letters · 2015Article
Corrections and comments
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Authors and funding
3 authors.
Funding
Abstract
Steryl glycosides produced by bacteria play important biological roles in the evasion and modulation of host immunity. Step-economical syntheses of three cholesteryl-6-O-phosphatidyl-α-D-glucopyranosides (αCPG) unique to Helicobacter pylori have been achieved. The approach relies upon regioselective deprotection of per-O-trimethylsilyl-α-D-cholesterylglucoside at C6 followed by phosphoramidite coupling. Global TMS ether deprotection in the presence of oxygen and subsequent deprotection of the cyano ethyl phosphoester afforded the target compounds in 16-21 % overall yield starting from D-glucose. The structures of these natural products were determined using a combination of 2D NMR methods and mass spectrometry. These robust synthesis and characterization protocols provide analogues to facilitate glycolipidomic profiling and biological studies.
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Registered trials
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