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Literature summary for 2.2.1.7 extracted from

  • Morris, F.; Vierling, R.; Boucher, L.; Bosch, J.; Freel Meyers, C.L.
    DXP synthase-catalyzed C-N bond formation: nitroso substrate specificity studies guide selective inhibitor design (2013), ChemBioChem, 14, 1309-1315.
    View publication on PubMedView publication on EuropePMC

Protein Variants

Protein Variants Comment Organism
R420A the mutation has no apparent effect on the affinities of nitroso substrates in C-N bond formation Escherichia coli
R478A the mutation has no apparent effect on the affinities of nitroso substrates in C-N bond formation Escherichia coli

Inhibitors

Inhibitors Comment Organism Structure
1-methyl-2-nitrosobenzene weak inhibitory activity Escherichia coli
1-nitrosonaphthalen-2-ol weak inhibitory activity Escherichia coli
3,5-dimethyl-4-nitroso-1-(propan-2-yl)-1H-pyrazole weak inhibitory activity Escherichia coli
6-bromo-1-nitrosonaphthalen-2-ol weak inhibitory activity Escherichia coli
6-hydroxy-5-nitrosonaphthalene-2-sulfonamide weak inhibitory activity Escherichia coli
7-methoxy-1-nitrosonaphthalen-2-ol weak inhibitory activity Escherichia coli
benzylacetylphosphonate competitive inhibitor Escherichia coli
N,N-dimethyl-4-nitrosoaniline weak inhibitory activity Escherichia coli
nitrosobenzene weak inhibitory activity Escherichia coli

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.018
-
6-hydroxy-5-nitrosonaphthalene-2-sulfonamide at pH 8.0 and 37°C Escherichia coli
0.024
-
6-bromo-1-nitrosonaphthalen-2-ol at pH 8.0 and 37°C Escherichia coli
0.041
-
1-nitrosonaphthalen-2-ol at pH 8.0 and 37°C Escherichia coli
0.054
-
N,N-dimethyl-4-nitrosoaniline at pH 8.0 and 37°C Escherichia coli
0.063
-
7-methoxy-1-nitrosonaphthalen-2-ol at pH 8.0 and 37°C Escherichia coli
0.099
-
1-methyl-2-nitrosobenzene at pH 8.0 and 37°C Escherichia coli
0.387
-
3,5-dimethyl-4-nitroso-1-(propan-2-yl)-1H-pyrazole at pH 8.0 and 37°C Escherichia coli
0.512
-
2-hydroxy-4,6-dinitrobenzaldehyde at pH 8.0 and 37°C Escherichia coli

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
pyruvate + D-glyceraldehyde 3-phosphate Escherichia coli
-
1-deoxy-D-xylulose 5-phosphate + CO2
-
?

Organism

Organism UniProt Comment Textmining
Escherichia coli P77488
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
pyruvate + 1-methyl-2-nitrosobenzene
-
Escherichia coli N-hydroxy-N-(2-methylphenyl)acetamide + CO2
-
?
pyruvate + 1-nitrosonaphthalen-2-ol
-
Escherichia coli N-hydroxy-N-(2-hydroxynaphthalen-1-yl)acetamide + CO2
-
?
pyruvate + 2-hydroxy-4,6-dinitrobenzaldehyde
-
Escherichia coli ? + CO2
-
?
pyruvate + 3,5-dimethyl-4-nitroso-1-(propan-2-yl)-1H-pyrazole
-
Escherichia coli N-[3,5-dimethyl-1-(propan-2-yl)-1H-pyrazol-4-yl]-N-hydroxyacetamide + CO2
-
?
pyruvate + 6-bromo-1-nitrosonaphthalen-2-ol
-
Escherichia coli N-(6-bromo-2-hydroxynaphthalen-1-yl)-N-hydroxyacetamide + CO2
-
?
pyruvate + 6-hydroxy-5-nitrosonaphthalene-2-sulfonamide
-
Escherichia coli N-hydroxy-N-(2-hydroxy-6-sulfamoylnaphthalen-1-yl)acetamide + CO2
-
?
pyruvate + 7-methoxy-1-nitrosonaphthalen-2-ol
-
Escherichia coli N-hydroxy-N-(2-hydroxy-7-methoxynaphthalen-1-yl)acetamide + CO2
-
?
pyruvate + D-glyceraldehyde 3-phosphate
-
Escherichia coli 1-deoxy-D-xylulose 5-phosphate + CO2
-
?
pyruvate + N,N-dimethyl-4-nitrosoaniline
-
Escherichia coli N-[4-(dimethylamino)phenyl]-N-hydroxyacetamide + CO2
-
?
pyruvate + nitrosobenzene
-
Escherichia coli ? + CO2
-
?
pyruvate + nitrosobenzene
-
Escherichia coli N-hydroxy-N-phenylacetamide + CO2
-
?

Synonyms

Synonyms Comment Organism
1-deoxy-D-xylulose 5-phosphate synthase
-
Escherichia coli
DXP synthase
-
Escherichia coli

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
0.006
-
2-hydroxy-4,6-dinitrobenzaldehyde at pH 8.0 and 37°C Escherichia coli
0.015
-
N,N-dimethyl-4-nitrosoaniline at pH 8.0 and 37°C Escherichia coli
0.018
-
1-nitrosonaphthalen-2-ol at pH 8.0 and 37°C Escherichia coli
0.02
-
6-hydroxy-5-nitrosonaphthalene-2-sulfonamide at pH 8.0 and 37°C Escherichia coli
0.022
-
7-methoxy-1-nitrosonaphthalen-2-ol at pH 8.0 and 37°C Escherichia coli
0.023
-
3,5-dimethyl-4-nitroso-1-(propan-2-yl)-1H-pyrazole at pH 8.0 and 37°C Escherichia coli
0.033
-
6-bromo-1-nitrosonaphthalen-2-ol at pH 8.0 and 37°C Escherichia coli
0.6
-
1-methyl-2-nitrosobenzene at pH 8.0 and 37°C Escherichia coli

Cofactor

Cofactor Comment Organism Structure
thiamine diphosphate
-
Escherichia coli

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.0104
-
benzylacetylphosphonate at pH 8.0 and 37°C Escherichia coli

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.208
-
at pH 8.0 and 37°C Escherichia coli nitrosobenzene
0.291
-
at pH 8.0 and 37°C Escherichia coli 1-methyl-2-nitrosobenzene
0.354
-
at pH 8.0 and 37°C Escherichia coli 6-hydroxy-5-nitrosonaphthalene-2-sulfonamide
0.522
-
at pH 8.0 and 37°C Escherichia coli 6-bromo-1-nitrosonaphthalen-2-ol
0.844
-
at pH 8.0 and 37°C Escherichia coli N,N-dimethyl-4-nitrosoaniline
1.065
-
at pH 8.0 and 37°C Escherichia coli 1-nitrosonaphthalen-2-ol
2
-
IC50 above 2.0 mM, at pH 8.0 and 37°C Escherichia coli 7-methoxy-1-nitrosonaphthalen-2-ol
2
-
IC50 above 2.0 mM, at pH 8.0 and 37°C Escherichia coli 3,5-dimethyl-4-nitroso-1-(propan-2-yl)-1H-pyrazole

kcat/KM [mM/s]

kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
0.045
-
1-nitrosonaphthalen-2-ol at pH 8.0 and 37°C Escherichia coli
0.06
-
3,5-dimethyl-4-nitroso-1-(propan-2-yl)-1H-pyrazole at pH 8.0 and 37°C Escherichia coli
0.28
-
N,N-dimethyl-4-nitrosoaniline at pH 8.0 and 37°C Escherichia coli
0.35
-
7-methoxy-1-nitrosonaphthalen-2-ol at pH 8.0 and 37°C Escherichia coli
1.1
-
6-hydroxy-5-nitrosonaphthalene-2-sulfonamide at pH 8.0 and 37°C Escherichia coli
1.3
-
6-bromo-1-nitrosonaphthalen-2-ol at pH 8.0 and 37°C Escherichia coli
6
-
1-methyl-2-nitrosobenzene at pH 8.0 and 37°C Escherichia coli