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Literature summary for 3.5.1.108 extracted from
- Structure of the deacetylase LpxC bound to the antibiotic CHIR-090: Time-dependent inhibition and specificity in ligand binding (2007), Proc. Natl. Acad. Sci. USA, 104, 18433-18438.
Protein Variants
| Protein Variants | Comment | Organism |
|---|---|---|
| Q202W/G210S | less sensitive to N-((2S,3R)-3-hydroxy-1-(hydroxyamino)-1-oxobutan-2-yl)-4-((4-(morpholinomethyl)phenyl)ethynyl)benzamide than wild-type, that is inhibited about 75% by 4 nM N-((2S,3R)-3-hydroxy-1-(hydroxyamino)-1-oxobutan-2-yl)-4-((4-(morpholinomethyl)phenyl)ethynyl)benzamide | Escherichia coli |
| S214G | completely inhibited by 0.5 microM N-((2S,3R)-3-hydroxy-1-(hydroxyamino)-1-oxobutan-2-yl)-4-((4-(morpholinomethyl)phenyl)ethynyl)benzamide, wild-type under the same conditions 50% inhibited | Rhizobium leguminosarum |
| T179A | LpxC mutant is less sensitive to N-((2S,3R)-3-hydroxy-1-(hydroxyamino)-1-oxobutan-2-yl)-4-((4-(morpholinomethyl)phenyl)ethynyl)benzamide inhibition | Aquifex aeolicus |
| W206Q/S214G | completely inhibited by 0.5 microM N-((2S,3R)-3-hydroxy-1-(hydroxyamino)-1-oxobutan-2-yl)-4-((4-(morpholinomethyl)phenyl)ethynyl)benzamide, wild-type under the same conditions 50% inhibited | Rhizobium leguminosarum |
Inhibitors
| Inhibitors | Comment | Organism | Structure |
|---|---|---|---|
| (R)-3-(5,8-dihydronaphthalen-2-yl)-N-hydroxy-2-(naphthalene-2-sulfonamido)propanamide | - |
Escherichia coli |  |
| (R)-3-(5,8-dihydronaphthalen-2-yl)-N-hydroxy-2-(naphthalene-2-sulfonamido)propanamide | - |
Rhizobium leguminosarum | |
| (S)-N-(1-(2-(3,4-dimethoxy-5-propylphenyl)-4,5-dihydrooxazol-4-yl)vinyl)hydroxylamine | - |
Escherichia coli | |
| (S)-N-(1-(2-(3,4-dimethoxy-5-propylphenyl)-4,5-dihydrooxazol-4-yl)vinyl)hydroxylamine | - |
Rhizobium leguminosarum | |
| additional information | (S)-N-(1-(2-(3,4-dimethoxy-5-propylphenyl)-4,5-dihydrooxazol-4-yl)vinyl)hydroxylamine and (R)-3-(5,8-dihydronaphthalen-2-yl)-N-hydroxy-2-(naphthalene-2-sulfonamido)propanamide do not inhibit Aquifex aeolicus LpxC | Aquifex aeolicus | |
| additional information | no evidence of time-dependent inhibition is observed in assays with either the wild-type or mutants | Rhizobium leguminosarum | |
| N-((2S,3R)-3-hydroxy-1-(hydroxyamino)-1-oxobutan-2-yl)-4-((4-(morpholinomethyl)phenyl)ethynyl)benzamide | as effectively as ciprofloxacin or tobramycin | Aquifex aeolicus | |
| N-((2S,3R)-3-hydroxy-1-(hydroxyamino)-1-oxobutan-2-yl)-4-((4-(morpholinomethyl)phenyl)ethynyl)benzamide | as effectively as ciprofloxacin or tobramycin | Escherichia coli | |
| N-((2S,3R)-3-hydroxy-1-(hydroxyamino)-1-oxobutan-2-yl)-4-((4-(morpholinomethyl)phenyl)ethynyl)benzamide | wild-type is insensitive to N-((2S,3R)-3-hydroxy-1-(hydroxyamino)-1-oxobutan-2-yl)-4-((4-(morpholinomethyl)phenyl)ethynyl)benzamide | Rhizobium leguminosarum | |
Organism
| Organism | UniProt | Comment | Textmining |
|---|---|---|---|
| Aquifex aeolicus | O67648 | - |
- |
| Escherichia coli | - |
- |
- |
| Rhizobium leguminosarum | Q1ME43 | - |
- |
Synonyms
| Synonyms | Comment | Organism |
|---|---|---|
| deacetylase LpxC | - |
Escherichia coli |
| deacetylase LpxC | - |
Aquifex aeolicus |
| deacetylase LpxC | - |
Rhizobium leguminosarum |
| LpxC | - |
Escherichia coli |
| LpxC | - |
Aquifex aeolicus |
| LpxC | - |
Rhizobium leguminosarum |
| UDP-3-O-(R-3-hydroxyacyl)-N-acetylglucosamine deacetylase | - |
Escherichia coli |
| UDP-3-O-(R-3-hydroxyacyl)-N-acetylglucosamine deacetylase | - |
Aquifex aeolicus |
| UDP-3-O-(R-3-hydroxyacyl)-N-acetylglucosamine deacetylase | - |
Rhizobium leguminosarum |
Ki Value [mM]
| Ki Value [mM] | Ki Value maximum [mM] | Inhibitor | Comment | Organism | Structure |
|---|---|---|---|---|---|
| 0.000003 | - |
N-((2S,3R)-3-hydroxy-1-(hydroxyamino)-1-oxobutan-2-yl)-4-((4-(morpholinomethyl)phenyl)ethynyl)benzamide | W206Q/S214G mutant | Rhizobium leguminosarum | |
| 0.0000035 | - |
N-((2S,3R)-3-hydroxy-1-(hydroxyamino)-1-oxobutan-2-yl)-4-((4-(morpholinomethyl)phenyl)ethynyl)benzamide | S214G mutant | Rhizobium leguminosarum | |
| 0.000004 | - |
N-((2S,3R)-3-hydroxy-1-(hydroxyamino)-1-oxobutan-2-yl)-4-((4-(morpholinomethyl)phenyl)ethynyl)benzamide | wild-type | Escherichia coli | |
| 0.000005 | - |
N-((2S,3R)-3-hydroxy-1-(hydroxyamino)-1-oxobutan-2-yl)-4-((4-(morpholinomethyl)phenyl)ethynyl)benzamide | Q202W/G210S mutant | Escherichia coli | |
| 0.000053 | - |
(S)-N-(1-(2-(3,4-dimethoxy-5-propylphenyl)-4,5-dihydrooxazol-4-yl)vinyl)hydroxylamine | wild-type | Escherichia coli | |
| 0.000069 | - |
(R)-3-(5,8-dihydronaphthalen-2-yl)-N-hydroxy-2-(naphthalene-2-sulfonamido)propanamide | wild-type | Escherichia coli | |
| 0.000086 | - |
(R)-3-(5,8-dihydronaphthalen-2-yl)-N-hydroxy-2-(naphthalene-2-sulfonamido)propanamide | Q202W/G210S mutant | Escherichia coli | |
| 0.00034 | - |
N-((2S,3R)-3-hydroxy-1-(hydroxyamino)-1-oxobutan-2-yl)-4-((4-(morpholinomethyl)phenyl)ethynyl)benzamide | wild-type | Rhizobium leguminosarum | |
| 0.00034 | - |
(S)-N-(1-(2-(3,4-dimethoxy-5-propylphenyl)-4,5-dihydrooxazol-4-yl)vinyl)hydroxylamine | Q202W/G210S mutant | Escherichia coli | |
| 0.0007 | - |
(R)-3-(5,8-dihydronaphthalen-2-yl)-N-hydroxy-2-(naphthalene-2-sulfonamido)propanamide | W206Q/S214G mutant | Rhizobium leguminosarum | |
| 0.0058 | - |
(R)-3-(5,8-dihydronaphthalen-2-yl)-N-hydroxy-2-(naphthalene-2-sulfonamido)propanamide | wild-type | Rhizobium leguminosarum | |
| 0.11 | - |
(S)-N-(1-(2-(3,4-dimethoxy-5-propylphenyl)-4,5-dihydrooxazol-4-yl)vinyl)hydroxylamine | W206Q/S214G mutant | Rhizobium leguminosarum | |
| 0.38 | - |
(S)-N-(1-(2-(3,4-dimethoxy-5-propylphenyl)-4,5-dihydrooxazol-4-yl)vinyl)hydroxylamine | wild-type | Rhizobium leguminosarum | |
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