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Literature summary for 3.5.1.108 extracted from

  • Pirrung, M.C.; Tumey, L.N.; McClerren, A.L.; Raetz, C.R.
    High-throughput catch-and-release synthesis of oxazoline hydroxamates. Structure-activity relationships in novel inhibitors of Escherichia coli LpxC: in vitro enzyme inhibition and antibacterial properties (2003), J. Am. Chem. Soc., 125, 1575-1586.
    View publication on PubMed

Protein Variants

Protein Variants Comment Organism
G17S hypersensitive strain with point mutation in LpxC Escherichia coli

Inhibitors

Inhibitors Comment Organism Structure
(4R)-N-hydroxy-2-tricyclo[3.3.1.1-3,7]dec-1-yl-4,5-dihydro-1,3-oxazole-4-carboxamide 1 microg/ml, high inhibitory activity Escherichia coli
(R)-2-(2-bromophenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide 1 microg/ml, nearly complete loss of activity Escherichia coli
(R)-2-(3,4-dichlorophenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide 1 microg/ml, exellent biological activity Escherichia coli
(R)-2-(3,4-difluorophenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide 1 microg/ml, exellent biological activity Escherichia coli
(R)-2-(3,4-dimethoxy-5-propylphenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide 1 microg/ml Escherichia coli
(R)-2-(3,5-dichlorophenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide 1 microg/ml, moderate activity Escherichia coli
(R)-2-(3,5-difluoro-4-methoxyphenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide 1 microg/ml, good activity Escherichia coli
(R)-2-(3,5-difluorophenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide 1 microg/ml, moderate activity Escherichia coli
(R)-2-(3,5-dimethoxyphenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide 1 microg/ml, 67% inhibition Escherichia coli
(R)-2-(3-(dichloromethyl)phenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide 1 microg/ml Escherichia coli
(R)-2-(3-bromo-4-fluorophenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide 1 microg/ml, exellent biological activity Escherichia coli
(R)-2-(3-chloro-4-fluorophenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide 1 microg/ml, exellent biological activity Escherichia coli
(R)-2-(3-cyanophenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide 1 microg/ml Escherichia coli
(R)-2-(3-fluoro-4-(trifluoromethyl)phenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide 1 microg/ml, slight lower inhibitory activity than (R)-2-(4-fluoro-3-(trifluoromethyl)phenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide Escherichia coli
(R)-2-(3-fluoro-5-(trifluoromethyl)phenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide 1 microg/ml, good activity Escherichia coli
(R)-2-(4-(hexyloxy)phenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide 1 microg/ml, 86% inhibition Escherichia coli
(R)-2-(4-(hydroxycarbamoyl)-4,5-dihydrooxazol-2-yl)benzyl benzoate 1 microg/ml, nearly complete loss of activity Escherichia coli
(R)-2-(4-chloro-3-nitrophenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide 1 microg/ml Escherichia coli
(R)-2-(4-fluoro-3-(trifluoromethyl)phenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide 1 microg/ml, most potent compound Escherichia coli
(R)-2-(4-fluoro-3-nitrophenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide 1 microg/ml Escherichia coli
(R)-2-(4-tert-butylphenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide 1 microg/ml, 58% inhibition Escherichia coli
(R)-2-(biphenyl-4-yl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide 1 microg/ml, 69% inhibition Escherichia coli
(R)-2-decyl-N-hydroxy-4,5-dihydrooxazole-4-carboxamide 1 microg/ml, high inhibitory activity Escherichia coli
(R)-N-hydroxy-2-(2,3,5-trifluoro-4-methoxyphenyl)-4,5-dihydrooxazole-4-carboxamide 1 microg/ml, good activity Escherichia coli
(R)-N-hydroxy-2-(2-methylprop-1-enyl)-4,5-dihydrooxazole-4-carboxamide 1 microg/ml, moderate activity Escherichia coli
(R)-N-hydroxy-2-(3,4,5-triethoxyphenyl)-4,5-dihydrooxazole-4-carboxamide 1 microg/ml, 72% inhibition Escherichia coli
(R)-N-hydroxy-2-(3-(trifluoromethoxy)phenyl)-4,5-dihydrooxazole-4-carboxamide 1 microg/ml, exellent inhibitory activity Escherichia coli
(R)-N-hydroxy-2-(3-methoxyphenyl)-4,5-dihydrooxazole-4-carboxamide 1 microg/ml, 44% inhibition Escherichia coli
(R)-N-hydroxy-2-(4-(trifluoromethoxy)phenyl)-4,5-dihydrooxazole-4-carboxamide 1 microg/ml Escherichia coli
(R)-N-hydroxy-2-(4-methoxy-3,5-dimethylphenyl)-4,5-dihydrooxazole-4-carboxamide 1 microg/ml, 71% inhibition Escherichia coli
(R)-N-hydroxy-2-(4-methoxy-3-nitrophenyl)-4,5-dihydrooxazole-4-carboxamide 1 microg/ml Escherichia coli
(R)-N-hydroxy-2-(4-methoxyphenyl)-4,5-dihydrooxazole-4-carboxamide 1 microg/ml Escherichia coli
(R)-N-hydroxy-2-(4-methyl-3-nitrophenyl)-4,5-dihydrooxazole-4-carboxamide 1 microg/ml Escherichia coli
(R)-N-hydroxy-2-(4-nitrophenyl)-4,5-dihydrooxazole-4-carboxamide 1 microg/ml Escherichia coli
(R,E)-2-(2-chlorostyryl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide 1 microg/ml, moderate activity Escherichia coli
(R,E)-N-hydroxy-2-(3-(trifluoromethyl)styryl)-4,5-dihydrooxazole-4-carboxamide 1 microg/ml, moderate activity Escherichia coli
(R,E)-N-hydroxy-2-(4-nitrostyryl)-4,5-dihydrooxazole-4-carboxamide 1 microg/ml, moderate activity Escherichia coli
(R,E)-N-hydroxy-2-styryl-4,5-dihydrooxazole-4-carboxamide 1 microg/ml, moderate activity Escherichia coli

Metals/Ions

Metals/Ions Comment Organism Structure
Zn2+ zinc amidase Escherichia coli

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
additional information Escherichia coli catalyses the second step of lipid A biosynthesis in Gram-negative bacteria ?
-
?

Organism

Organism UniProt Comment Textmining
Escherichia coli
-
wild-type and LpxC inhibitor-sensitive strain
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
additional information catalyses the second step of lipid A biosynthesis in Gram-negative bacteria Escherichia coli ?
-
?
UDP-3-O-((R)-3-hydroxymyristoyl)-N-acetylglucosamine + H2O
-
Escherichia coli UDP-3-O-((R)-3-hydroxymyristoyl)-D-glucosamine + acetate
-
?

Synonyms

Synonyms Comment Organism
deacetylase
-
Escherichia coli
LpxC
-
Escherichia coli

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
30
-
assay at Escherichia coli

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7.4
-
assay at Escherichia coli

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.000097
-
-
Escherichia coli (R)-2-(3,4-dimethoxy-5-propylphenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
0.00033
-
-
Escherichia coli (R)-2-(3,5-difluoro-4-methoxyphenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
0.00075
-
-
Escherichia coli (R)-2-(4-(hexyloxy)phenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
0.0016
-
-
Escherichia coli (R)-N-hydroxy-2-(2,3,5-trifluoro-4-methoxyphenyl)-4,5-dihydrooxazole-4-carboxamide
0.0068
-
-
Escherichia coli (R)-2-(3,5-difluorophenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide