Synthesis and biological evaluation of flexible and conformationally constrained LpxC inhibitors.

@article{Lppenberg2013SynthesisAB,
  title={Synthesis and biological evaluation of flexible and conformationally constrained LpxC inhibitors.},
  author={Marius L{\"o}ppenberg and H. M{\"u}ller and Carla Pulina and A. Oddo and M. Teese and J. Jose and Ralph Holl},
  journal={Organic & biomolecular chemistry},
  year={2013},
  volume={11 36},
  pages={
          6056-70
        }
}
Inhibitors of the UDP-3-O-[(R)-3-hydroxymyristoyl]-N-acetylglucosamine deacetylase (LpxC) represent promising candidates for the development of antibiotics possessing a so far unexploited mechanism of action. In a chiral pool synthesis, starting from the D-mannose derived mannonolactone 4, conformationally constrained C-glycosidic as well as open chained hydroxamic acids with a defined stereochemistry were prepared. Diversity was introduced by performing C–C coupling reactions like the… Expand
View on PubMed
rsc.org
24 Citations
Background Citations
1

24 Citations

Citation Type

Citation Type

Chiral pool synthesis and biological evaluation of C-furanosidic and acyclic LpxC inhibitors.
  • 10
Development of novel LpxC inhibitors: chiral-pool synthesis of C-triazolyl glycosides
  • 10
Synthesis, biological evaluation and molecular docking studies of benzyloxyacetohydroxamic acids as LpxC inhibitors.
  • 15
Synthesis and biological evaluation of C -ethynyl furanosides as LpxC inhibitors
  • 3
Synthesis and biological evaluation of enantiomerically pure glyceric acid derivatives as LpxC inhibitors.
  • 5
C-Triazolyl β-d-furanosides as LpxC inhibitors: stereoselective synthesis and biological evaluation
  • 9
Synthesis and biological evaluation of triazolyl-substituted benzyloxyacetohydroxamic acids as LpxC inhibitors.
  • 1
Insights into the Zinc-Dependent Deacetylase LpxC: Biochemical Properties and Inhibitor Design.
  • 15
Chiral Pool Synthesis, Biological Evaluation and Molecular Docking Studies of C‐Furanosidic LpxC Inhibitors
  • 1
Phenylethylene glycol-derived LpxC inhibitors with diverse Zn2+-binding groups
  • 2
  • PDF
...
1
2
3
...

References

SHOWING 1-10 OF 27 REFERENCES
Design and stereoselective synthesis of a C-aryl furanoside as a conformationally constrained CHIR-090 analogue.
  • 20
Inhibition of lipid A biosynthesis as the primary mechanism of CHIR-090 antibiotic activity in Escherichia coli.
  • 75
  • PDF
Structure of the deacetylase LpxC bound to the antibiotic CHIR-090: Time-dependent inhibition and specificity in ligand binding
  • 78
  • PDF
Antibacterial Agents That Target Lipid A Biosynthesis in Gram-negative Bacteria
  • 140
  • PDF
Activation of Escherichia coli UDP-3-O-[(R)-3-hydroxymyristoyl]-N-acetylglucosamine deacetylase by Fe2+ yields a more efficient enzyme with altered ligand affinity.
  • 30
Antibacterial Activities and Characterization of Novel Inhibitors of LpxC
  • 139
  • PDF
A slow, tight-binding inhibitor of the zinc-dependent deacetylase LpxC of lipid A biosynthesis with antibiotic activity comparable to ciprofloxacin.
  • 111
Crystal structure of LpxC, a zinc-dependent deacetylase essential for endotoxin biosynthesis
  • 120
  • PDF
Species-specific and inhibitor-dependent conformations of LpxC: implications for antibiotic design.
  • 73
  • PDF
Synthesis of a carbohydrate-derived hydroxamic acid inhibitor of the bacterial enzyme (LpxC) involved in lipid A biosynthesis.
  • 46
...
1
2
3
...