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Literature summary for 1.1.1.267 extracted from

  • Munier, M.; Tritsch, D.; Krebs, F.; Esque, J.; Hemmerlin, A.; Rohmer, M.; Stote, R.; Grosdemange-Billiard, C.
    Synthesis and biological evaluation of phosphate isosters of fosmidomycin and analogs as inhibitors of Escherichia coli and Mycobacterium smegmatis 1-deoxyxylulose 5-phosphate reductoisomerases (2017), Bioorg. Med. Chem., 25, 684-689 .
    View publication on PubMed
Search for more literature for 1.1.1.267

Application

Application Comment Organism
drug development the enzyme from Escherichia coli is a valuable target for the development of antimicrobial compounds Escherichia coli
drug development the enzyme from Mycobacterium smegmatis is a valuable target for the development of antimicrobial compounds Mycolicibacterium smegmatis

Inhibitors

Inhibitors Comment Organism Structure
2-[acetyl(methyl)amino]ethyl phosphate
-
 Escherichia coli
2-[acetyl(methyl)amino]ethyl phosphate
-
 Mycolicibacterium smegmatis
3-(hydroxyamino)-3-oxopropyl phosphate
-
 Escherichia coli
3-(hydroxyamino)-3-oxopropyl phosphate
-
 Mycolicibacterium smegmatis
3-[hydroxy(methyl)amino]-3-oxopropyl phosphate
-
 Escherichia coli
3-[hydroxy(methyl)amino]-3-oxopropyl phosphate
-
 Mycolicibacterium smegmatis
fosfoxacin
-
 Escherichia coli
fosfoxacin
-
 Mycolicibacterium smegmatis
fosmidomycin a naturally occurring retrohydroxamate phosphonic acid. DXR-NADPH-fosmidomycin complex crystal structure analysis, the phosphonate group of the inhibitor is located in the phosphate binding cleft of the substrate DXP and is bound in a similar fashion as the phosphate group Escherichia coli
fosmidomycin a naturally occurring retrohydroxamate phosphonic acid. DXR-NADPH-fosmidomycin complex crystal structure analysis, the phosphonate group of the inhibitor is located in the phosphate binding cleft of the substrate DXP and is bound in a similar fashion as the phosphate group Mycolicibacterium smegmatis
FR-900098 a naturally occurring retrohydroxamate phosphonic acid, isolated from the filtrate of a Pseudomonas fluorescens PK-52 culture Mycolicibacterium smegmatis
FR900098 a naturally occurring retrohydroxamate phosphonic acid Escherichia coli
additional information hydroxamate analogues of fosfoxacin, the phosphate homologue of fosmidomycin, as inhibitors of DXR, synthesis and activities, analysis of Escherichia coli strain XL-1 Blue cell growth inhibition, overview Escherichia coli
additional information hydroxamate analogues of fosfoxacin, the phosphate homologue of fosmidomycin, as inhibitors of DXR, synthesis and activities, overview Mycolicibacterium smegmatis
[4-(hydroxyamino)-4-oxobutyl]phosphonic acid
-
 Escherichia coli
[4-(hydroxyamino)-4-oxobutyl]phosphonic acid
-
 Mycolicibacterium smegmatis
[4-[hydroxy(methyl)amino]-4-oxobutyl]phosphonic acid
-
 Escherichia coli
[4-[hydroxy(methyl)amino]-4-oxobutyl]phosphonic acid
-
 Mycolicibacterium smegmatis

Metals/Ions

Metals/Ions Comment Organism Structure
Mg2+ required Escherichia coli
Mg2+ required Mycolicibacterium smegmatis

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1-deoxy-D-xylulose 5-phosphate + NADPH + H+ Escherichia coli
-
 2-C-methyl-D-erythritol 4-phosphate + NADP+
-
 ?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+ Mycolicibacterium smegmatis
-
 2-C-methyl-D-erythritol 4-phosphate + NADP+
-
 ?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+ Mycolicibacterium smegmatis ATCC 700084
-
 2-C-methyl-D-erythritol 4-phosphate + NADP+
-
 ?

Organism

Organism UniProt Comment Textmining
Escherichia coli P45568
-
-
Mycolicibacterium smegmatis A0QVH7
-
-
Mycolicibacterium smegmatis ATCC 700084 A0QVH7
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
-
 Escherichia coli 2-C-methyl-D-erythritol 4-phosphate + NADP+
-
 ?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
-
 Mycolicibacterium smegmatis 2-C-methyl-D-erythritol 4-phosphate + NADP+
-
 ?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
-
 Mycolicibacterium smegmatis ATCC 700084 2-C-methyl-D-erythritol 4-phosphate + NADP+
-
 ?

Synonyms

Synonyms Comment Organism
1-deoxyxylulose 5-phosphate reductoisomerase
-
 Escherichia coli
1-deoxyxylulose 5-phosphate reductoisomerase
-
 Mycolicibacterium smegmatis
DXR
-
 Escherichia coli
DXR
-
 Mycolicibacterium smegmatis

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
37
-
 assay at Escherichia coli
37
-
 assay at Mycolicibacterium smegmatis

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7.5
-
 assay at Escherichia coli
7.5
-
 assay at Mycolicibacterium smegmatis

Cofactor

Cofactor Comment Organism Structure
NADP+
-
 Escherichia coli
NADP+
-
 Mycolicibacterium smegmatis
NADPH
-
 Escherichia coli
NADPH
-
 Mycolicibacterium smegmatis

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.000004
-
 pH 7.5, 37°C, recombinant His-tagged enzyme Escherichia coli FR900098
0.000042
-
 pH 7.5, 37°C, recombinant His-tagged enzyme Escherichia coli fosmidomycin
0.000046
-
 pH 7.5, 37°C, recombinant His-tagged enzyme Escherichia coli 3-[hydroxy(methyl)amino]-3-oxopropyl phosphate
0.000048
-
 pH 7.5, 37°C, recombinant His-tagged enzyme Escherichia coli [4-[hydroxy(methyl)amino]-4-oxobutyl]phosphonic acid
0.000077
-
 pH 7.5, 37°C, recombinant His-tagged enzyme Escherichia coli 2-[acetyl(methyl)amino]ethyl phosphate
0.00017
-
 pH 7.5, 37°C, recombinant His-tagged enzyme Escherichia coli [4-(hydroxyamino)-4-oxobutyl]phosphonic acid
0.000233
-
 pH 7.5, 37°C, recombinant His-tagged enzyme Mycolicibacterium smegmatis 3-[hydroxy(methyl)amino]-3-oxopropyl phosphate
0.000279
-
 pH 7.5, 37°C, recombinant His-tagged enzyme Mycolicibacterium smegmatis 2-[acetyl(methyl)amino]ethyl phosphate
0.00032
-
 pH 7.5, 37°C, recombinant His-tagged enzyme Mycolicibacterium smegmatis FR-900098
0.000342
-
 pH 7.5, 37°C, recombinant His-tagged enzyme Escherichia coli fosfoxacin
0.00041
-
 pH 7.5, 37°C, recombinant His-tagged enzyme Mycolicibacterium smegmatis [4-[hydroxy(methyl)amino]-4-oxobutyl]phosphonic acid
0.00051
-
 pH 7.5, 37°C, recombinant His-tagged enzyme Mycolicibacterium smegmatis fosmidomycin
0.00148
-
 pH 7.5, 37°C, recombinant His-tagged enzyme Mycolicibacterium smegmatis [4-(hydroxyamino)-4-oxobutyl]phosphonic acid
0.0021
-
 pH 7.5, 37°C, recombinant His-tagged enzyme Mycolicibacterium smegmatis fosfoxacin
0.0026
-
 pH 7.5, 37°C, recombinant His-tagged enzyme Escherichia coli 3-(hydroxyamino)-3-oxopropyl phosphate
0.0092
-
 pH 7.5, 37°C, recombinant His-tagged enzyme Mycolicibacterium smegmatis 3-(hydroxyamino)-3-oxopropyl phosphate

General Information

General Information Comment Organism
physiological function in many pathogenic bacteria, the enzymes of the 2-C-methyl-D-erythrirol 4-phosphate (MEP) pathway are involved in the biosynthesis of isopentenyl diphosphate and dimethylallyl diphosphate, the two universal and essential units for the biosynthesis of isoprenoids. The enzyme 1-deoxyxylulose 5-phosphate reductoisomerase (DXR) that catalyzes the transformation of 1-deoxy-D-xylulose 5-phosphate (DXP) to 2-C-methyl-D-erythritol 4-phosphate (MEP) via an isomerization and a NADPH-dependent reduction reaction Escherichia coli
physiological function in many pathogenic bacteria, the enzymes of the 2-C-methyl-D-erythrirol 4-phosphate (MEP) pathway are involved in the biosynthesis of isopentenyl diphosphate and dimethylallyl diphosphate, the two universal and essential units for the biosynthesis of isoprenoids. The enzyme 1-deoxyxylulose 5-phosphate reductoisomerase (DXR) that catalyzes the transformation of 1-deoxy-D-xylulose 5-phosphate (DXP) to 2-C-methyl-D-erythritol 4-phosphate (MEP) via an isomerization and a NADPH-dependent reduction reaction Mycolicibacterium smegmatis