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Syntheses, structures and antibiotic activities of LpxC inhibitors based on the diacetylene scaffold.

Publication ,  Journal Article
Liang, X; Lee, C-J; Chen, X; Chung, HS; Zeng, D; Raetz, CRH; Li, Y; Zhou, P; Toone, EJ
Published in: Bioorg Med Chem
January 15, 2011

Compounds inhibiting LpxC in the lipid A biosynthetic pathway are promising leads for novel antibiotics against multidrug-resistant Gram-negative pathogens. We report the syntheses and structural and biochemical characterizations of LpxC inhibitors based on a diphenyl-diacetylene (1,4-diphenyl-1,3-butadiyne) threonyl-hydroxamate scaffold. These studies provide a molecular interpretation for the differential antibiotic activities of compounds with a substituted distal phenyl ring as well as the absolute stereochemical requirement at the C2, but not C3, position of the threonyl group.

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Published In

Bioorg Med Chem

DOI

EISSN

1464-3391

Publication Date

January 15, 2011

Volume

19

Issue

2

Start / End Page

852 / 860

Location

England

Related Subject Headings

  • Structure-Activity Relationship
  • Protein Structure, Tertiary
  • Molecular Sequence Data
  • Microbial Sensitivity Tests
  • Medicinal & Biomolecular Chemistry
  • Escherichia coli Proteins
  • Escherichia coli
  • Enzyme Inhibitors
  • Computer Simulation
  • Binding Sites
 

Citation

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Liang, X., Lee, C.-J., Chen, X., Chung, H. S., Zeng, D., Raetz, C. R. H., … Toone, E. J. (2011). Syntheses, structures and antibiotic activities of LpxC inhibitors based on the diacetylene scaffold. Bioorg Med Chem, 19(2), 852–860. https://doi.org/10.1016/j.bmc.2010.12.017
Liang, Xiaofei, Chul-Jin Lee, Xin Chen, Hak Suk Chung, Daina Zeng, Christian R. H. Raetz, Yaoxian Li, Pei Zhou, and Eric J. Toone. “Syntheses, structures and antibiotic activities of LpxC inhibitors based on the diacetylene scaffold.Bioorg Med Chem 19, no. 2 (January 15, 2011): 852–60. https://doi.org/10.1016/j.bmc.2010.12.017.
Liang X, Lee C-J, Chen X, Chung HS, Zeng D, Raetz CRH, et al. Syntheses, structures and antibiotic activities of LpxC inhibitors based on the diacetylene scaffold. Bioorg Med Chem. 2011 Jan 15;19(2):852–60.
Liang, Xiaofei, et al. “Syntheses, structures and antibiotic activities of LpxC inhibitors based on the diacetylene scaffold.Bioorg Med Chem, vol. 19, no. 2, Jan. 2011, pp. 852–60. Pubmed, doi:10.1016/j.bmc.2010.12.017.
Liang X, Lee C-J, Chen X, Chung HS, Zeng D, Raetz CRH, Li Y, Zhou P, Toone EJ. Syntheses, structures and antibiotic activities of LpxC inhibitors based on the diacetylene scaffold. Bioorg Med Chem. 2011 Jan 15;19(2):852–860.
Journal cover image

Published In

Bioorg Med Chem

DOI

EISSN

1464-3391

Publication Date

January 15, 2011

Volume

19

Issue

2

Start / End Page

852 / 860

Location

England

Related Subject Headings

  • Structure-Activity Relationship
  • Protein Structure, Tertiary
  • Molecular Sequence Data
  • Microbial Sensitivity Tests
  • Medicinal & Biomolecular Chemistry
  • Escherichia coli Proteins
  • Escherichia coli
  • Enzyme Inhibitors
  • Computer Simulation
  • Binding Sites