ArticleBioorganic & medicinal chemistry letters2011
N-methylimidazolium chloride-catalyzed pyrophosphate formation: application to the synthesis of Lipid I and NDP-sugar donors.
Article in Bioorganic & medicinal chemistry letters, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
What it found
Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.
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.
The trial behind it
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.
Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.
Who cites it
12 citing papers in PubMed, 39 citations in OpenAlex.
- Chemoenzymatic Synthesis and Purification of Bioorthogonally Tagged UDP-GlcNAc and UDP-GalNAc Analogues.Current protocols · 2025Article
- Facile Synthesis of Carbamoyl FluoridesACS omega · 2025Article
- Feedback Inhibition of Bacterial Nucleotidyltransferases by Rare Nucleotide l-Sugars Restricts Substrate Promiscuity.Journal of the American Chemical Society · 2023Article
- Staphylococcus aureus cell growth and division are regulated by an amidase that trims peptides from uncrosslinked peptidoglycan.Nature microbiology · 2020Article
- Engineering Orthogonal Polypeptide GalNAc-Transferase and UDP-Sugar Pairs.Journal of the American Chemical Society · 2019Article
- Lipid II overproduction allows direct assay of transpeptidase inhibition by β-lactams.Nature chemical biology · 2017Article
- In vitro reconstitution demonstrates the cell wall ligase activity of LCP proteins.Nature chemical biology · 2017Article
- Detection of lipid-linked peptidoglycan precursors by exploiting an unexpected transpeptidase reaction.Journal of the American Chemical Society · 2014Article
- Reconstitution of peptidoglycan cross-linking leads to improved fluorescent probes of cell wall synthesis.Journal of the American Chemical Society · 2014Article
- Staphylococcus aureus Penicillin-Binding Protein 2 Can Use Depsi-Lipid II Derived from Vancomycin-Resistant Strains for Cell Wall Synthesis.Chemistry (Weinheim an der Bergstrasse, Germany) · 2013Article
- Forming cross-linked peptidoglycan from synthetic gram-negative Lipid II.Journal of the American Chemical Society · 2013Article
- Modular synthesis of diphospholipid oligosaccharide fragments of the bacterial cell wall and their use to study the mechanism of moenomycin and other antibiotics.Tetrahedron · 2011Article
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
2 authors at 1 institution in 1 country.
Funding
Abstract
N-Methylimidazolium chloride is found to catalyze a coupling reaction between monophosphates and activated phosphorous-nitrogen intermediates such as a phosphorimidazolide and phosphoromorpholidate to form biologically important unsymmetrical pyrophosphate diesters. The catalyst is much more active, cheaper, and less explosive than 1H-tetrazole, known as the best catalyst for the pyrophosphate formation over a decade. The mild and neutral reaction conditions are compatible with allylic pyrophosphate formation in Lipid I syntheisis. (31)P NMR experiments suggest that the catalyst acts not only as an acid but also as a nucleophile to form cationic and electrophilic phosphor-N-methylimidazolide intermediates in the pyrophosphate formation.
Indexed as
Identifiers
What OpenQuestion holds
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.