BRENDA - Enzyme Database
show all sequences of 1.3.1.118

Phosphorylation of InhA inhibits mycolic acid biosynthesis and growth of Mycobacterium tuberculosis

Molle, V.; Gulten, G.; Vilcheze, C.; Veyron-Churlet, R.; Zanella-Cleon, I.; Sacchettini, J.; Jacobs Jr, W.; Kremer, L.; Mol. Microbiol. 78, 1591-1605 (2010)

Data extracted from this reference:

Cloned(Commentary)
Cloned (Commentary)
Organism
the inhA gene is cloned into the pMK1 mycobacterial expression vector under the control of the strong promoter hsp60. The resulting construct is used to transform Mycobacterium bovis BCG Pasteur in order to allow overproduction of recombinant His-tagged InhA
Mycobacterium tuberculosis
Engineering
Protein Variants
Commentary
Organism
T266A
phosphoablative mutant with activity similar to wild-type enzyme
Mycobacterium tuberculosis
T266D
phosphomimetic mutant with strongly reduced activity (31.4% compared to wild-type enzyme), introduction of inhA_T266D fails to complement growth and mycolic acid defects of an inhA-thermosensitive Mycobacterium smegmatis strain, in a similar manner to what is observed following isoniazid treatment
Mycobacterium tuberculosis
T266E
phosphomimetic mutant with strongly reduced activity (29.5% compared to wild-type enzyme), introduction of inhA_T266E fails to complement growth and mycolic acid defects of an inhA-thermosensitive Mycobacterium smegmatis strain, in a similar manner to what is observed following isoniazid treatment
Mycobacterium tuberculosis
KM Value [mM]
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
0.0196
-
trans-2-dodecenoyl-CoA
pH 7.5, 25°C, mutant enzyme T266D
Mycobacterium tuberculosis
0.0203
-
trans-2-dodecenoyl-CoA
pH 7.5, 25°C, mutant enzyme T266E
Mycobacterium tuberculosis
0.0409
-
trans-2-dodecenoyl-CoA
pH 7.5, 25°C, wild-type enzyme
Mycobacterium tuberculosis
0.0523
-
trans-2-dodecenoyl-CoA
pH 7.5, 25°C, mutant enzyme T266A
Mycobacterium tuberculosis
Organism
Organism
UniProt
Commentary
Textmining
Mycobacterium tuberculosis
P9WGR1
-
-
Mycobacterium tuberculosis ATCC 25618
P9WGR1
-
-
Posttranslational Modification
Posttranslational Modification
Commentary
Organism
phosphoprotein
InhA is phosphorylated in vitro by multiple Ser/Thr kinases on residue Thr266.. Activity of InhA is controlled via phosphorylation. Thr266 is the unique kinase phosphoacceptor, both in vitro and in vivo. The physiological relevance of Thr266 phosphorylation is demonstrated using inhA phosphoablative (T266A) or phosphomimetic (T266D/E) mutants. Enoyl reductase activity is severely impaired in the mimetic mutants in vitro, as a consequence of a reduced binding affinity to NADH. Introduction of inhA_T266D/E fails to complement growth and mycolic acid defects of an inhA-thermosensitive Mycobacterium smegmatis strain, in a similar manner to what is observed following isoniazid treatment. Phosphorylation of InhA may represent an unusual mechanism that allows Mycobacterium tuberculosis to regulate its mycolic acid content, thus offering a new approach to future anti-tuberculosis drug development
Mycobacterium tuberculosis
Purification (Commentary)
Purification (Commentary)
Organism
-
Mycobacterium tuberculosis
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
Substrate Product ID
trans-2-dodecenoyl-CoA + NADH + H+
-
748680
Mycobacterium tuberculosis
dodecanoyl-CoA + NAD+
-
-
-
?
trans-2-dodecenoyl-CoA + NADH + H+
-
748680
Mycobacterium tuberculosis ATCC 25618
dodecanoyl-CoA + NAD+
-
-
-
?
Turnover Number [1/s]
Turnover Number Minimum [1/s]
Turnover Number Maximum [1/s]
Substrate
Commentary
Organism
Structure
1.46
-
trans-2-dodecenoyl-CoA
pH 7.5, 25°C, mutant enzyme T266D
Mycobacterium tuberculosis
2.49
-
trans-2-dodecenoyl-CoA
pH 7.5, 25°C, mutant enzyme T266E
Mycobacterium tuberculosis
5.34
-
trans-2-dodecenoyl-CoA
pH 7.5, 25°C, wild-type enzyme
Mycobacterium tuberculosis
7.12
-
trans-2-dodecenoyl-CoA
pH 7.5, 25°C, mutant enzyme T266A
Mycobacterium tuberculosis
Cofactor
Cofactor
Commentary
Organism
Structure
NADH
-
Mycobacterium tuberculosis
Cloned(Commentary) (protein specific)
Commentary
Organism
the inhA gene is cloned into the pMK1 mycobacterial expression vector under the control of the strong promoter hsp60. The resulting construct is used to transform Mycobacterium bovis BCG Pasteur in order to allow overproduction of recombinant His-tagged InhA
Mycobacterium tuberculosis
Cofactor (protein specific)
Cofactor
Commentary
Organism
Structure
NADH
-
Mycobacterium tuberculosis
Engineering (protein specific)
Protein Variants
Commentary
Organism
T266A
phosphoablative mutant with activity similar to wild-type enzyme
Mycobacterium tuberculosis
T266D
phosphomimetic mutant with strongly reduced activity (31.4% compared to wild-type enzyme), introduction of inhA_T266D fails to complement growth and mycolic acid defects of an inhA-thermosensitive Mycobacterium smegmatis strain, in a similar manner to what is observed following isoniazid treatment
Mycobacterium tuberculosis
T266E
phosphomimetic mutant with strongly reduced activity (29.5% compared to wild-type enzyme), introduction of inhA_T266E fails to complement growth and mycolic acid defects of an inhA-thermosensitive Mycobacterium smegmatis strain, in a similar manner to what is observed following isoniazid treatment
Mycobacterium tuberculosis
KM Value [mM] (protein specific)
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
0.0196
-
trans-2-dodecenoyl-CoA
pH 7.5, 25°C, mutant enzyme T266D
Mycobacterium tuberculosis
0.0203
-
trans-2-dodecenoyl-CoA
pH 7.5, 25°C, mutant enzyme T266E
Mycobacterium tuberculosis
0.0409
-
trans-2-dodecenoyl-CoA
pH 7.5, 25°C, wild-type enzyme
Mycobacterium tuberculosis
0.0523
-
trans-2-dodecenoyl-CoA
pH 7.5, 25°C, mutant enzyme T266A
Mycobacterium tuberculosis
Posttranslational Modification (protein specific)
Posttranslational Modification
Commentary
Organism
phosphoprotein
InhA is phosphorylated in vitro by multiple Ser/Thr kinases on residue Thr266.. Activity of InhA is controlled via phosphorylation. Thr266 is the unique kinase phosphoacceptor, both in vitro and in vivo. The physiological relevance of Thr266 phosphorylation is demonstrated using inhA phosphoablative (T266A) or phosphomimetic (T266D/E) mutants. Enoyl reductase activity is severely impaired in the mimetic mutants in vitro, as a consequence of a reduced binding affinity to NADH. Introduction of inhA_T266D/E fails to complement growth and mycolic acid defects of an inhA-thermosensitive Mycobacterium smegmatis strain, in a similar manner to what is observed following isoniazid treatment. Phosphorylation of InhA may represent an unusual mechanism that allows Mycobacterium tuberculosis to regulate its mycolic acid content, thus offering a new approach to future anti-tuberculosis drug development
Mycobacterium tuberculosis
Purification (Commentary) (protein specific)
Commentary
Organism
-
Mycobacterium tuberculosis
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
ID
trans-2-dodecenoyl-CoA + NADH + H+
-
748680
Mycobacterium tuberculosis
dodecanoyl-CoA + NAD+
-
-
-
?
trans-2-dodecenoyl-CoA + NADH + H+
-
748680
Mycobacterium tuberculosis ATCC 25618
dodecanoyl-CoA + NAD+
-
-
-
?
Turnover Number [1/s] (protein specific)
Turnover Number Minimum [1/s]
Turnover Number Maximum [1/s]
Substrate
Commentary
Organism
Structure
1.46
-
trans-2-dodecenoyl-CoA
pH 7.5, 25°C, mutant enzyme T266D
Mycobacterium tuberculosis
2.49
-
trans-2-dodecenoyl-CoA
pH 7.5, 25°C, mutant enzyme T266E
Mycobacterium tuberculosis
5.34
-
trans-2-dodecenoyl-CoA
pH 7.5, 25°C, wild-type enzyme
Mycobacterium tuberculosis
7.12
-
trans-2-dodecenoyl-CoA
pH 7.5, 25°C, mutant enzyme T266A
Mycobacterium tuberculosis
General Information
General Information
Commentary
Organism
metabolism
the enzyme is an essential enzyme of the mycolic acid biosynthetic pathway
Mycobacterium tuberculosis
General Information (protein specific)
General Information
Commentary
Organism
metabolism
the enzyme is an essential enzyme of the mycolic acid biosynthetic pathway
Mycobacterium tuberculosis
KCat/KM [mM/s]
kcat/KM Value [1/mMs-1]
kcat/KM Value Maximum [1/mMs-1]
Substrate
Commentary
Organism
Structure
74.49
-
trans-2-dodecenoyl-CoA
pH 7.5, 25°C, mutant enzyme T266D
Mycobacterium tuberculosis
122.7
-
trans-2-dodecenoyl-CoA
pH 7.5, 25°C, mutant enzyme T266E
Mycobacterium tuberculosis
130.6
-
trans-2-dodecenoyl-CoA
pH 7.5, 25°C, wild-type enzyme
Mycobacterium tuberculosis
136.13
-
trans-2-dodecenoyl-CoA
pH 7.5, 25°C, mutant enzyme T266A
Mycobacterium tuberculosis
KCat/KM [mM/s] (protein specific)
KCat/KM Value [1/mMs-1]
KCat/KM Value Maximum [1/mMs-1]
Substrate
Commentary
Organism
Structure
74.49
-
trans-2-dodecenoyl-CoA
pH 7.5, 25°C, mutant enzyme T266D
Mycobacterium tuberculosis
122.7
-
trans-2-dodecenoyl-CoA
pH 7.5, 25°C, mutant enzyme T266E
Mycobacterium tuberculosis
130.6
-
trans-2-dodecenoyl-CoA
pH 7.5, 25°C, wild-type enzyme
Mycobacterium tuberculosis
136.13
-
trans-2-dodecenoyl-CoA
pH 7.5, 25°C, mutant enzyme T266A
Mycobacterium tuberculosis
Other publictions for EC 1.3.1.118
No.
1st author
Pub Med
title
organims
journal
volume
pages
year
Activating Compound
Application
Cloned(Commentary)
Crystallization (Commentary)
Engineering
General Stability
Inhibitors
KM Value [mM]
Localization
Metals/Ions
Molecular Weight [Da]
Natural Substrates/ Products (Substrates)
Organic Solvent Stability
Organism
Oxidation Stability
Posttranslational Modification
Purification (Commentary)
Reaction
Renatured (Commentary)
Source Tissue
Specific Activity [micromol/min/mg]
Storage Stability
Substrates and Products (Substrate)
Subunits
Synonyms
Temperature Optimum [°C]
Temperature Range [°C]
Temperature Stability [°C]
Turnover Number [1/s]
pH Optimum
pH Range
pH Stability
Cofactor
Ki Value [mM]
pI Value
IC50 Value
Activating Compound (protein specific)
Application (protein specific)
Cloned(Commentary) (protein specific)
Cofactor (protein specific)
Crystallization (Commentary) (protein specific)
Engineering (protein specific)
General Stability (protein specific)
IC50 Value (protein specific)
Inhibitors (protein specific)
Ki Value [mM] (protein specific)
KM Value [mM] (protein specific)
Localization (protein specific)
Metals/Ions (protein specific)
Molecular Weight [Da] (protein specific)
Natural Substrates/ Products (Substrates) (protein specific)
Organic Solvent Stability (protein specific)
Oxidation Stability (protein specific)
Posttranslational Modification (protein specific)
Purification (Commentary) (protein specific)
Renatured (Commentary) (protein specific)
Source Tissue (protein specific)
Specific Activity [micromol/min/mg] (protein specific)
Storage Stability (protein specific)
Substrates and Products (Substrate) (protein specific)
Subunits (protein specific)
Temperature Optimum [°C] (protein specific)
Temperature Range [°C] (protein specific)
Temperature Stability [°C] (protein specific)
Turnover Number [1/s] (protein specific)
pH Optimum (protein specific)
pH Range (protein specific)
pH Stability (protein specific)
pI Value (protein specific)
Expression
General Information
General Information (protein specific)
Expression (protein specific)
KCat/KM [mM/s]
KCat/KM [mM/s] (protein specific)
747250
Joshi
Pharmacophore mapping, molecu ...
Mycobacterium tuberculosis, Mycobacterium tuberculosis H37Rv
Bioorg. Chem.
81
440-453
2018
-
-
1
1
-
-
5
-
-
-
-
-
-
13
-
-
1
-
-
-
-
-
2
-
2
-
-
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-
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-
-
-
-
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-
1
-
1
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5
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1
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2
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-
1
1
-
-
-
747697
Chollet
An overview on crystal struct ...
Mycobacterium tuberculosis, Mycobacterium tuberculosis ATCC 25618
Eur. J. Med. Chem.
146
318-343
2018
-
1
-
1
7
-
5
-
-
-
-
-
-
20
-
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-
-
-
-
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-
1
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2
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1
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1
7
-
2
5
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-
-
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-
-
-
-
-
-
-
-
-
2
2
-
-
-
748518
Xia
Discovery of a cofactor-indep ...
Mycobacterium tuberculosis, Mycobacterium tuberculosis ATCC 25618
Life Sci. Alliance
1
e201800025
2018
-
-
1
-
8
-
6
-
-
-
-
-
-
22
-
-
1
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1
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6
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1
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8
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6
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1
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-
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-
-
-
-
748042
Spagnuolo
Evaluating the contribution o ...
Mycobacterium tuberculosis, Mycobacterium tuberculosis ATCC 25618
J. Am. Chem. Soc.
139
3417-3429
2017
-
-
-
1
-
-
18
-
-
-
-
-
-
19
-
-
1
-
-
-
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-
1
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-
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17
-
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-
-
1
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-
18
17
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1
-
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-
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-
-
-
-
-
-
747582
Guardia
N-Benzyl-4-((heteroaryl)methy ...
Mycobacterium tuberculosis, Mycobacterium tuberculosis ATCC 25618
ChemMedChem
11
687-701
2016
-
-
1
-
-
-
26
-
-
-
-
-
-
19
-
-
1
-
-
-
-
-
2
-
1
1
-
-
-
1
-
-
1
-
-
28
-
-
1
1
-
-
-
28
26
-
-
-
-
-
-
-
-
-
1
-
-
-
-
2
-
1
-
-
-
1
-
-
-
-
-
-
-
-
-
747703
Rotta
Piperazine derivatives Synthe ...
Mycobacterium tuberculosis, Mycobacterium tuberculosis ATCC 25618
Eur. J. Med. Chem.
90
436-447
2015
-
-
-
-
-
-
10
-
-
-
-
-
-
19
-
-
-
-
-
-
-
-
2
-
2
-
-
-
-
-
-
-
1
-
-
9
-
-
-
1
-
-
-
9
10
-
-
-
-
-
-
-
-
-
-
-
-
-
-
2
-
-
-
-
-
-
-
-
-
-
1
1
-
-
-
747700
Pedgaonkar
Development of 2-(4-oxoquinaz ...
Mycobacterium tuberculosis, Mycobacterium tuberculosis ATCC 25618
Eur. J. Med. Chem.
86
613-627
2014
-
1
1
-
-
-
28
-
-
-
-
-
-
19
-
-
-
-
-
-
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-
2
-
2
1
-
-
-
1
-
-
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-
-
16
-
1
1
-
-
-
-
16
28
-
-
-
-
-
-
-
-
-
-
-
-
-
-
2
-
1
-
-
-
1
-
-
-
-
-
-
-
-
-
747629
Pan
Targeting InhA, the FASII eno ...
Mycobacterium tuberculosis
Curr. Top. Med. Chem.
12
672-693
2012
-
-
-
-
-
-
1
-
-
-
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-
1
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2
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1
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-
-
-
-
-
748433
Da Costa
Conformational changes in 2-t ...
Mycobacterium tuberculosis, Mycobacterium tuberculosis ATCC 25618
J. Mol. Model.
18
1779-1790
2012
-
-
-
-
1
-
2
-
-
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-
-
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19
-
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2
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1
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2
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-
-
-
-
-
-
-
-
-
-
-
-
-
1
1
-
-
-
748167
Luckner
A slow, tight binding inhibit ...
Mycobacterium tuberculosis, Mycobacterium tuberculosis ATCC 25618
J. Biol. Chem.
285
14330-14337
2010
-
-
1
1
-
-
1
-
-
-
-
-
-
19
-
-
1
-
-
-
-
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-
2
-
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-
-
-
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-
1
-
2
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1
-
1
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2
1
1
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1
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-
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-
-
-
-
-
-
-
-
748277
Vasconcelos
-
Kinetic and equilibrium mecha ...
Mycobacterium tuberculosis
J. Braz. Chem. Soc.
21
1503-1508
2010
-
-
-
-
-
-
-
-
-
-
-
-
-
1
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1
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1
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2
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1
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1
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-
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-
748516
Gurvitz
Triclosan inhibition of mycob ...
Mycobacterium tuberculosis
Lett. Appl. Microbiol.
50
399-405
2010
-
-
1
-
-
-
2
-
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-
1
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1
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1
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2
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-
1
1
-
-
-
748622
Lu
Recent progress in the identi ...
Mycobacterium tuberculosis, Mycobacterium tuberculosis ATCC 25618
Mini Rev. Med. Chem.
10
182-193
2010
-
-
-
-
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-
18
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-
19
-
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1
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-
5
-
5
-
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-
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5
18
5
-
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-
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-
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-
-
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-
-
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-
-
-
-
-
-
748680
Molle
Phosphorylation of InhA inhib ...
Mycobacterium tuberculosis, Mycobacterium tuberculosis ATCC 25618
Mol. Microbiol.
78
1591-1605
2010
-
-
1
-
3
-
-
4
-
-
-
-
-
19
-
1
1
-
-
-
-
-
2
-
-
-
-
-
4
-
-
-
1
-
-
-
-
-
1
1
-
3
-
-
-
-
4
-
-
-
-
-
-
1
1
-
-
-
-
2
-
-
-
-
4
-
-
-
-
-
1
1
-
4
4
747498
Subba Rao
Structure-based design of a n ...
Mycobacterium tuberculosis, Mycobacterium tuberculosis ATCC 25618
Chem. Biol. Drug Des.
72
444-449
2008
-
-
-
-
-
-
2
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-
19
-
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1
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-
1
1
-
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-
747251
He
Inhibition of the Mycobacteri ...
Mycobacterium tuberculosis, Mycobacterium tuberculosis ATCC 25618
Bioorg. Med. Chem.
15
6649-6658
2007
-
-
-
1
-
-
12
-
-
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-
-
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19
-
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-
-
-
-
-
-
2
-
1
-
-
-
-
-
-
-
-
-
-
6
-
-
-
-
1
-
-
6
12
-
-
-
-
-
-
-
-
-
-
-
-
-
-
2
-
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New insight into the mechanis ...
Mycobacterium tuberculosis, Mycobacterium tuberculosis ATCC 25618
J. Am. Chem. Soc.
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9582-9583
2007
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749238
Kruh
Probing mechanisms of resista ...
Mycobacterium tuberculosis, Mycobacterium tuberculosis ATCC 25618
Protein Sci.
16
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2007
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1
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3
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1
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19
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1
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1
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747286
Schroeder
Molecular dynamics simulation ...
Mycobacterium tuberculosis, Mycobacterium tuberculosis ATCC 25618
Biophys. J.
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876-884
2005
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1
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746762
Nguyen
Mn(III) pyrophosphate as an e ...
Mycobacterium tuberculosis
Antimicrob. Agents Chemother.
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2002
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1
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2
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2
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1
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1
1
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747579
Nguyen
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The nonenzymatic activation o ...
Mycobacterium tuberculosis
Chemistry
4
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2001
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1
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1
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1
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1
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1
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1
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1
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1
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1
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1
1
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748073
Vilcheze
Inactivation of the inhA-enco ...
Mycolicibacterium smegmatis, Mycolicibacterium smegmatis mc(2)155
J. Bacteriol.
182
4059-4067
2000
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1
1
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748605
Marrakchi
InhA, a target of the antitub ...
Mycobacterium tuberculosis, Mycobacterium tuberculosis mc(2)155
Microbiology
146
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2000
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2
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Rozwarski
Crystal structure of the Myco ...
Mycobacterium tuberculosis, Mycobacterium tuberculosis ATCC 25618
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274
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1999
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2
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1
1
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747053
Quemard
Enzymatic characterization of ...
Mycobacterium tuberculosis, Mycobacterium tuberculosis ATCC 25618
Biochemistry
34
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1995
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1
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1
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12
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1
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20
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1
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10
1
1
1
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1
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1
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1
1
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1
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1
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12
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1
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1
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10
1
1
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1
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1
1
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