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Literature summary for 2.2.1.7 extracted from

  • Bartee, D.; Freel Meyers, C.L.
    Targeting the unique mechanism of bacterial 1-deoxy-D-xylulose-5-phosphate synthase (2018), Biochemistry, 57, 4349-4356 .
    View publication on PubMedView publication on EuropePMC

Protein Variants

Protein Variants Comment Organism
R478A the mutant shows reduced affinity for D-glyceraldehyde 3-phosphate compared to the wild type enzyme Escherichia coli

Inhibitors

Inhibitors Comment Organism Structure
(2R)-2-(4-[2-[(acetylphosphinato)oxy]ethyl]-1H-1,2,3-triazol-1-yl)-3-(4-hydroxyphenyl)propanoate
-
Escherichia coli
(2R)-2-(4-[2-[(acetylphosphinato)oxy]ethyl]-1H-1,2,3-triazol-1-yl)-3-phenylpropanoate most potent selective inhibitor Escherichia coli
(2R)-2-(4-[2-[(acetylphosphinato)oxy]ethyl]-1H-1,2,3-triazol-1-yl)propanoate
-
Escherichia coli
(2S)-2-(4-[2-[(acetylphosphinato)oxy]ethyl]-1H-1,2,3-triazol-1-yl)-3-(4-hydroxyphenyl)propanoate
-
Escherichia coli
(2S)-2-(4-[2-[(acetylphosphinato)oxy]ethyl]-1H-1,2,3-triazol-1-yl)-3-phenylpropanoate
-
Escherichia coli
(2S)-2-(4-[2-[(acetylphosphinato)oxy]ethyl]-1H-1,2,3-triazol-1-yl)propanoate
-
Escherichia coli
2-(1-benzyl-1H-1,2,3-triazol-4-yl)ethyl acetylphosphonate
-
Escherichia coli
2-(1-cyclohexyl-1H-1,2,3-triazol-4-yl)ethyl acetylphosphonate
-
Escherichia coli
2-(1-pentyl-1H-1,2,3-triazol-4-yl)ethyl acetylphosphonate
-
Escherichia coli
2-(1-[(2S)-1-[methyl(4-methylbenzene-1-sulfonyl)amino]-1-oxo-3-phenylpropan-2-yl]-1H-1,2,3-triazol-4-yl)ethyl acetylphosphonate
-
Escherichia coli
2-(1-[2-[methyl(methylsulfonyl)amino]-2-oxoethyl]-1H-1,2,3-triazol-4-yl)ethyl acetylphosphonate
-
Escherichia coli
2-[1-(2-hydroxyethyl)-1H-1,2,3-triazol-4-yl]ethyl acetylphosphonate
-
Escherichia coli
2-[1-(2-hydroxyphenyl)-1H-1,2,3-triazol-4-yl]ethyl acetylphosphonate
-
Escherichia coli
2-[1-(2-methoxy-2-oxoethyl)-1H-1,2,3-triazol-4-yl]ethyl acetylphosphonate
-
Escherichia coli
2-[1-(2-nitrobenzyl)-1H-1,2,3-triazol-4-yl]ethyl acetylphosphonate
-
Escherichia coli
2-[1-(2-phenylethyl)-1H-1,2,3-triazol-4-yl]ethyl acetylphosphonate
-
Escherichia coli
2-[1-(2-[methyl[(4-methylphenyl)sulfonyl]amino]-2-oxoethyl)-1H-1,2,3-triazol-4-yl]ethyl acetylphosphonate
-
Escherichia coli
2-[1-(3-hydroxyphenyl)-1H-1,2,3-triazol-4-yl]ethyl acetylphosphonate
-
Escherichia coli
2-[1-(4-hydroxyphenyl)-1H-1,2,3-triazol-4-yl]ethyl acetylphosphonate
-
Escherichia coli
2-[1-(4-nitrobenzyl)-1H-1,2,3-triazol-4-yl]ethyl acetylphosphonate
-
Escherichia coli
2-[1-(carboxymethyl)-1H-1,2,3-triazol-4-yl]ethyl acetylphosphonate
-
Escherichia coli
2-[1-(prop-2-en-1-yl)-1H-1,2,3-triazol-4-yl]ethyl acetylphosphonate
-
Escherichia coli
2-[1-[4-(methoxycarbonyl)benzyl]-1H-1,2,3-triazol-4-yl]ethyl acetylphosphonate
-
Escherichia coli
butylacetylphosphonate
-
Escherichia coli
lithium but-3-yn-1-yl acetylphosphonate
-
Escherichia coli
Methylacetylphosphonate
-
Escherichia coli

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.042
-
D-glyceraldehyde 3-phosphate wild type enzyme, at pH 8.0 and 37°C Escherichia coli
2.3
-
D-glyceraldehyde 3-phosphate mutant enzyme R478A, 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
-
-
-

Substrates and Products (Substrate)

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

Synonyms

Synonyms Comment Organism
DXP synthase
-
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
0.00009
-
(2R)-2-(4-[2-[(acetylphosphinato)oxy]ethyl]-1H-1,2,3-triazol-1-yl)-3-phenylpropanoate at pH 8.0 and 37°C Escherichia coli
0.00011
-
2-[1-(2-hydroxyphenyl)-1H-1,2,3-triazol-4-yl]ethyl acetylphosphonate at pH 8.0 and 37°C Escherichia coli
0.00032
-
2-[1-(3-hydroxyphenyl)-1H-1,2,3-triazol-4-yl]ethyl acetylphosphonate at pH 8.0 and 37°C Escherichia coli
0.00033
-
(2R)-2-(4-[2-[(acetylphosphinato)oxy]ethyl]-1H-1,2,3-triazol-1-yl)-3-(4-hydroxyphenyl)propanoate at pH 8.0 and 37°C Escherichia coli
0.00044
-
2-(1-cyclohexyl-1H-1,2,3-triazol-4-yl)ethyl acetylphosphonate at pH 8.0 and 37°C Escherichia coli
0.00047
-
lithium but-3-yn-1-yl acetylphosphonate at pH 8.0 and 37°C Escherichia coli
0.00047
-
2-[1-(2-[methyl[(4-methylphenyl)sulfonyl]amino]-2-oxoethyl)-1H-1,2,3-triazol-4-yl]ethyl acetylphosphonate at pH 8.0 and 37°C Escherichia coli
0.00052
-
2-(1-[2-[methyl(methylsulfonyl)amino]-2-oxoethyl]-1H-1,2,3-triazol-4-yl)ethyl acetylphosphonate at pH 8.0 and 37°C Escherichia coli
0.00083
-
2-(1-[(2S)-1-[methyl(4-methylbenzene-1-sulfonyl)amino]-1-oxo-3-phenylpropan-2-yl]-1H-1,2,3-triazol-4-yl)ethyl acetylphosphonate at pH 8.0 and 37°C Escherichia coli
0.00084
-
2-[1-(carboxymethyl)-1H-1,2,3-triazol-4-yl]ethyl acetylphosphonate at pH 8.0 and 37°C Escherichia coli
0.001
-
2-[1-(2-hydroxyethyl)-1H-1,2,3-triazol-4-yl]ethyl acetylphosphonate at pH 8.0 and 37°C Escherichia coli
0.001
-
(2S)-2-(4-[2-[(acetylphosphinato)oxy]ethyl]-1H-1,2,3-triazol-1-yl)-3-(4-hydroxyphenyl)propanoate at pH 8.0 and 37°C Escherichia coli
0.0013
-
2-[1-(2-methoxy-2-oxoethyl)-1H-1,2,3-triazol-4-yl]ethyl acetylphosphonate at pH 8.0 and 37°C Escherichia coli
0.0013
-
(2S)-2-(4-[2-[(acetylphosphinato)oxy]ethyl]-1H-1,2,3-triazol-1-yl)propanoate at pH 8.0 and 37°C Escherichia coli
0.0021
-
(2S)-2-(4-[2-[(acetylphosphinato)oxy]ethyl]-1H-1,2,3-triazol-1-yl)-3-phenylpropanoate at pH 8.0 and 37°C Escherichia coli
0.0026
-
butylacetylphosphonate at pH 8.0 and 37°C Escherichia coli
0.0027
-
2-[1-(4-nitrobenzyl)-1H-1,2,3-triazol-4-yl]ethyl acetylphosphonate at pH 8.0 and 37°C Escherichia coli
0.0029
-
(2R)-2-(4-[2-[(acetylphosphinato)oxy]ethyl]-1H-1,2,3-triazol-1-yl)propanoate at pH 8.0 and 37°C Escherichia coli
0.003
-
2-(1-pentyl-1H-1,2,3-triazol-4-yl)ethyl acetylphosphonate at pH 8.0 and 37°C Escherichia coli
0.0054
-
2-[1-(2-nitrobenzyl)-1H-1,2,3-triazol-4-yl]ethyl acetylphosphonate at pH 8.0 and 37°C Escherichia coli
0.006
-
2-[1-(4-hydroxyphenyl)-1H-1,2,3-triazol-4-yl]ethyl acetylphosphonate at pH 8.0 and 37°C Escherichia coli
0.006
-
2-[1-(prop-2-en-1-yl)-1H-1,2,3-triazol-4-yl]ethyl acetylphosphonate at pH 8.0 and 37°C Escherichia coli
0.008
-
2-(1-benzyl-1H-1,2,3-triazol-4-yl)ethyl acetylphosphonate at pH 8.0 and 37°C Escherichia coli
0.008
-
2-[1-(2-phenylethyl)-1H-1,2,3-triazol-4-yl]ethyl acetylphosphonate at pH 8.0 and 37°C Escherichia coli
0.008
-
2-[1-[4-(methoxycarbonyl)benzyl]-1H-1,2,3-triazol-4-yl]ethyl acetylphosphonate at pH 8.0 and 37°C Escherichia coli

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.0018
-
wild type enzyme, at pH 8.0 and 37°C Escherichia coli Methylacetylphosphonate
0.005
-
mutant enzyme R478A, at pH 8.0 and 37°C Escherichia coli Methylacetylphosphonate