ArticleTetrahedron2011
Modular synthesis of diphospholipid oligosaccharide fragments of the bacterial cell wall and their use to study the mechanism of moenomycin and other antibiotics.
Article in Tetrahedron, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
What it found
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Who cites it
16 citing papers in PubMed, 36 citations in OpenAlex.
- Genetically engineered Streptomyces viridosporus ATCC 14672 strains for the discovery of novel moenomycins.Scientific reports · 2026Article
- Peptidoglycan polymerase function and regulation.Microbiology and molecular biology reviews : MMBR · 2025Review
- Structural diversity, bioactivity, and biosynthesis of phosphoglycolipid family antibiotics: Recent advances.BBA advances · 2022Article
- Unipolar Peptidoglycan Synthesis in themBio · 2021Article
- Formation of trisubstituted buta-1,3-dienes and α,β-unsaturated ketonesRSC advances · 2020Article
- Facile Synthesis of Sugar Lactols via Bromine-Mediated Oxidation of Thioglycosides.Journal of carbohydrate chemistry · 2019Article
- Article
- Glycosyltransferases and Transpeptidases/Penicillin-Binding Proteins: Valuable Targets for New Antibacterials.Antibiotics (Basel, Switzerland) · 2016Review
- Testing the utility of site-specific recombinases for manipulations of genome of moenomycin producer Streptomyces ghanaensis ATCC14672.Journal of applied genetics · 2015Article
- Prospects for novel inhibitors of peptidoglycan transglycosylases.Bioorganic chemistry · 2014Review
- Bioactive oligosaccharide natural products.Natural product reports · 2014Review
- MoeH5: a natural glycorandomizer from the moenomycin biosynthetic pathway.Molecular microbiology · 2013Article
- Forming cross-linked peptidoglycan from synthetic gram-negative Lipid II.Journal of the American Chemical Society · 2013Article
- Tuning the moenomycin pharmacophore to enable discovery of bacterial cell wall synthesis inhibitors.Journal of the American Chemical Society · 2013Article
- Peptidoglycan glycosyltransferase substrate mimics as templates for the design of new antibacterial drugs.Frontiers in immunology · 2013Article
- Synthesis and NMR characterization of (Z,Z,Z,Z,E,E,ω)-heptaprenol.Journal of the American Chemical Society · 2012Article
Corrections and comments
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Authors and funding
5 authors at 1 institution in 1 country.
Funding
Abstract
We present a flexible, modular route to GlcNAc-MurNAc-oligosaccharides that can be readily converted into peptidoglycan (PG) fragments to serve as reagents for the study of bacterial enzymes that are targets for antibiotics. Demonstrating the utility of these synthetic PG substrates, we show that the tetrasaccharide substrate lipid IV (3), but not the disaccharide substrate lipid II (2), significantly increases the concentration of moenomycin A required to inhibit a prototypical PG-glycosyltransferase (PGT). These results imply that lipid IV and moenomycin A bind to the same site on the enzyme. We also show the moenomycin A inhibits the formation of elongated polysaccharide product but does not affect length distribution. We conclude that moenomycin A blocks PG-strand initiation rather than elongation or chain termination. Synthetic access to diphospholipid oligosaccharides will enable further studies of bacterial cell wall synthesis with the long-term goal of identifying novel antibiotics.
Identifiers
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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.