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Literature summary for 1.1.1.267 extracted from

  • Bodill, T.; Conibear, A.C.; Mutorwa, M.K.; Goble, J.L.; Blatch, G.L.; Lobb, K.A.; Klein, R.; Kaye, P.T.
    Exploring DOXP-reductoisomerase binding limits using phosphonated N-aryl and N-heteroarylcarboxamides as DXR inhibitors (2013), Bioorg. Med. Chem., 21, 4332-4341.
    View publication on PubMed
Search for more literature for 1.1.1.267

Application

Application Comment Organism
drug development the enzyme is a target for the design of antimalarial drugs Plasmodium falciparum

Cloned(Commentary)

Cloned (Comment) Organism
recombinant expression of His-tagged enzyme Escherichia coli
recombinant expression of His-tagged enzyme Plasmodium falciparum

Inhibitors

Inhibitors Comment Organism Structure
(4-[[3-(hydroxymethyl)phenyl]amino]-4-oxobutyl)phosphonic acid 26.8% inhibition Escherichia coli
(4-[[3-(hydroxymethyl)phenyl]amino]-4-oxobutyl)phosphonic acid
-
 Plasmodium falciparum
diethyl (2-[[3-(hydroxymethyl)phenyl]amino]-2-oxoethyl)phosphonate 40.4% inhibition Escherichia coli
diethyl (2-[[3-(hydroxymethyl)phenyl]amino]-2-oxoethyl)phosphonate
-
 Plasmodium falciparum
diethyl (3-[[3-(hydroxymethyl)phenyl]amino]-3-oxopropyl)phosphonate 17.9% inhibition Escherichia coli
diethyl [2-[(3-bromophenyl)amino]-2-oxoethyl]phosphonate 21.4% inhibition Escherichia coli
diethyl [2-[(3-cyanophenyl)amino]-2-oxoethyl]phosphonate 11.9% inhibition Escherichia coli
diethyl [2-[(3-cyanophenyl)amino]-2-oxoethyl]phosphonate
-
 Plasmodium falciparum
diethyl [2-[(3-hydroxyphenyl)amino]-2-oxoethyl]phosphonate 24.4% inhibition Escherichia coli
diethyl [2-[(3-hydroxyphenyl)amino]-2-oxoethyl]phosphonate
-
 Plasmodium falciparum
diethyl [2-[(3-methoxyphenyl)amino]-2-oxoethyl]phosphonate 11% inhibition Escherichia coli
diethyl [3-[(3-hydroxyphenyl)amino]-3-oxopropyl]phosphonate 33.5% inhibition Escherichia coli
diethyl [3-[(3-methoxyphenyl)amino]-3-oxopropyl]phosphonate 14.1% inhibition Escherichia coli
fosmidomycin a natural product isolated from Streptomyces lavendulae Escherichia coli
fosmidomycin a natural product isolated from Streptomyces lavendulae Plasmodium falciparum
FR900098 an acetyl analogue of fosmidomycin Escherichia coli
FR900098 an acetyl analogue of fosmidomycin Plasmodium falciparum
additional information inhibitory potencies of a series of aryl- and heteroarylcarbamoylphosphonic acids, their diethyl esters and disodium salts as analogues of the potent DXR inhibitor fosmidomycin, effects of the carboxamide N-substituents and the length of the methylene linker, in silico docking studies, saturation transfer difference NMR spectroscopy and enzyme inhibition assays, overview. Molecular modelling and simulated docking studies. No or poor inhibition by diethyl (4-[[3-(hydroxymethyl)phenyl]amino]-4-oxobutyl)phosphonate, diethyl [5-[(3-hydroxyphenyl)amino]-5-oxopentyl]phosphonate, [3-[(3-hydroxyphenyl)amino]-3-oxopropyl]phosphonic acid, [5-[(3-bromophenyl)amino]-5-oxopentyl]phosphonic acid, diethyl [5-[(3-methoxyphenyl)amino]-5-oxopentyl]phosphonate, [4-[(3-methoxyphenyl)amino]-4-oxobutyl]phosphonic acid, [5-[(3-methoxyphenyl)amino]-5-oxopentyl]phosphonic acid, diethyl [4-[(3-bromophenyl)amino]-4-oxobutyl]phosphonate, [4-[(3-bromophenyl)amino]-4-oxobutyl]phosphonic acid, and [5-[(3-bromophenyl)amino]-5-oxopentyl]phosphonic acid Escherichia coli
additional information inhibitory potencies of a series of aryl- and heteroarylcarbamoylphosphonic acids, their diethyl esters and disodium salts as analogues of the potent DXR inhibitor fosmidomycin, effects of the carboxamide N-substituents and the length of the methylene linker, in silico docking studies, saturation transfer difference NMR spectroscopy and enzyme inhibition assays, overview. Molecular modelling and simulated docking studies. No or poor inhibition by diethyl [3-[(3-hydroxyphenyl)amino]-3-oxopropyl]phosphonate, diethyl [2-[(3-methoxyphenyl)amino]-2-oxoethyl]phosphonate, diethyl [3-[(3-methoxyphenyl)amino]-3-oxopropyl]phosphonate, diethyl [2-[(3-bromophenyl)amino]-2-oxoethyl]phosphonate, diethyl (3-[[3-(hydroxymethyl)phenyl]amino]-3-oxopropyl)phosphonate, [4-[(3-methoxyphenyl)amino]-4-oxobutyl]phosphonic acid, and [2-[(3-cyanophenyl)amino]-2-oxoethyl]phosphonic acid Plasmodium falciparum
[2-[(3-bromophenyl)amino]-2-oxoethyl]phosphonic acid
-
 Plasmodium falciparum
[2-[(3-cyanophenyl)amino]-2-oxoethyl]phosphonic acid 20.0% inhibition Escherichia coli
[2-[(3-hydroxyphenyl)amino]-2-oxoethyl]phosphonic acid 43.9% inhibition Escherichia coli
[2-[(3-hydroxyphenyl)amino]-2-oxoethyl]phosphonic acid
-
 Plasmodium falciparum
[2-[(3-methoxyphenyl)amino]-2-oxoethyl]phosphonic acid 17.8% inhibition Escherichia coli
[2-[(3-methoxyphenyl)amino]-2-oxoethyl]phosphonic acid
-
 Plasmodium falciparum
[4-[(3-bromophenyl)amino]-4-oxobutyl]phosphonic acid
-
 Plasmodium falciparum
[4-[(3-hydroxyphenyl)amino]-4-oxobutyl]phosphonic acid 49.2% inhibition Escherichia coli
[4-[(3-hydroxyphenyl)amino]-4-oxobutyl]phosphonic acid
-
 Plasmodium falciparum
[5-[(3-bromophenyl)amino]-5-oxopentyl]phosphonic acid 26.8% inhibition Escherichia coli

Metals/Ions

Metals/Ions Comment Organism Structure
Mg2+ required Escherichia coli
Mg2+ required Plasmodium falciparum

Organism

Organism UniProt Comment Textmining
Escherichia coli
-
-
-
Plasmodium falciparum
-
-
-

Purification (Commentary)

Purification (Comment) Organism
recombinant His-tagged enzyme by nickkel affinity chromatography and gel filtration Escherichia coli
recombinant His-tagged enzyme by nickkel affinity chromatography and gel filtration Plasmodium falciparum

Synonyms

Synonyms Comment Organism
1-deoxy-D-xylulose-5-phosphate reductoisomerase
-
 Escherichia coli
1-deoxy-D-xylulose-5-phosphate reductoisomerase
-
 Plasmodium falciparum
DOXP-reductoisomerase
-
 Escherichia coli
DOXP-reductoisomerase
-
 Plasmodium falciparum
DXR
-
 Escherichia coli
DXR
-
 Plasmodium falciparum

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
37
-
 assay at Escherichia coli
37
-
 assay at Plasmodium falciparum

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7.5
-
 assay at Escherichia coli
7.5
-
 assay at Plasmodium falciparum

General Information

General Information Comment Organism
metabolism the enzyme is involved in a parasite-specific, isoprenoid biosynthetic DOXP/MEP pathway Plasmodium falciparum
metabolism the enzyme is involved in the isoprenoid biosynthetic DOXP/MEP pathway Escherichia coli