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Literature summary 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

Application

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

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.1.1.267 2-[acetyl(methyl)amino]ethyl phosphate
-
 Escherichia coli
1.1.1.267 2-[acetyl(methyl)amino]ethyl phosphate
-
 Mycolicibacterium smegmatis
1.1.1.267 3-(hydroxyamino)-3-oxopropyl phosphate
-
 Escherichia coli
1.1.1.267 3-(hydroxyamino)-3-oxopropyl phosphate
-
 Mycolicibacterium smegmatis
1.1.1.267 3-[hydroxy(methyl)amino]-3-oxopropyl phosphate
-
 Escherichia coli
1.1.1.267 3-[hydroxy(methyl)amino]-3-oxopropyl phosphate
-
 Mycolicibacterium smegmatis
1.1.1.267 fosfoxacin
-
 Escherichia coli
1.1.1.267 fosfoxacin
-
 Mycolicibacterium smegmatis
1.1.1.267 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
1.1.1.267 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
1.1.1.267 FR-900098 a naturally occurring retrohydroxamate phosphonic acid, isolated from the filtrate of a Pseudomonas fluorescens PK-52 culture Mycolicibacterium smegmatis
1.1.1.267 FR900098 a naturally occurring retrohydroxamate phosphonic acid Escherichia coli
1.1.1.267 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
1.1.1.267 additional information hydroxamate analogues of fosfoxacin, the phosphate homologue of fosmidomycin, as inhibitors of DXR, synthesis and activities, overview Mycolicibacterium smegmatis
1.1.1.267 [4-(hydroxyamino)-4-oxobutyl]phosphonic acid
-
 Escherichia coli
1.1.1.267 [4-(hydroxyamino)-4-oxobutyl]phosphonic acid
-
 Mycolicibacterium smegmatis
1.1.1.267 [4-[hydroxy(methyl)amino]-4-oxobutyl]phosphonic acid
-
 Escherichia coli
1.1.1.267 [4-[hydroxy(methyl)amino]-4-oxobutyl]phosphonic acid
-
 Mycolicibacterium smegmatis

Metals/Ions

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

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.1.1.267 1-deoxy-D-xylulose 5-phosphate + NADPH + H+ Escherichia coli
-
 2-C-methyl-D-erythritol 4-phosphate + NADP+
-
 ?
1.1.1.267 1-deoxy-D-xylulose 5-phosphate + NADPH + H+ Mycolicibacterium smegmatis
-
 2-C-methyl-D-erythritol 4-phosphate + NADP+
-
 ?
1.1.1.267 1-deoxy-D-xylulose 5-phosphate + NADPH + H+ Mycolicibacterium smegmatis ATCC 700084
-
 2-C-methyl-D-erythritol 4-phosphate + NADP+
-
 ?

Organism

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

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.1.1.267 1-deoxy-D-xylulose 5-phosphate + NADPH + H+
-
 Escherichia coli 2-C-methyl-D-erythritol 4-phosphate + NADP+
-
 ?
1.1.1.267 1-deoxy-D-xylulose 5-phosphate + NADPH + H+
-
 Mycolicibacterium smegmatis 2-C-methyl-D-erythritol 4-phosphate + NADP+
-
 ?
1.1.1.267 1-deoxy-D-xylulose 5-phosphate + NADPH + H+
-
 Mycolicibacterium smegmatis ATCC 700084 2-C-methyl-D-erythritol 4-phosphate + NADP+
-
 ?

Synonyms

EC Number Synonyms Comment Organism
1.1.1.267 1-deoxyxylulose 5-phosphate reductoisomerase
-
 Escherichia coli
1.1.1.267 1-deoxyxylulose 5-phosphate reductoisomerase
-
 Mycolicibacterium smegmatis
1.1.1.267 DXR
-
 Escherichia coli
1.1.1.267 DXR
-
 Mycolicibacterium smegmatis

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
1.1.1.267 37
-
 assay at Escherichia coli
1.1.1.267 37
-
 assay at Mycolicibacterium smegmatis

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
1.1.1.267 7.5
-
 assay at Escherichia coli
1.1.1.267 7.5
-
 assay at Mycolicibacterium smegmatis

Cofactor

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

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
1.1.1.267 0.000004
-
 pH 7.5, 37°C, recombinant His-tagged enzyme Escherichia coli FR900098
1.1.1.267 0.000042
-
 pH 7.5, 37°C, recombinant His-tagged enzyme Escherichia coli fosmidomycin
1.1.1.267 0.000046
-
 pH 7.5, 37°C, recombinant His-tagged enzyme Escherichia coli 3-[hydroxy(methyl)amino]-3-oxopropyl phosphate
1.1.1.267 0.000048
-
 pH 7.5, 37°C, recombinant His-tagged enzyme Escherichia coli [4-[hydroxy(methyl)amino]-4-oxobutyl]phosphonic acid
1.1.1.267 0.000077
-
 pH 7.5, 37°C, recombinant His-tagged enzyme Escherichia coli 2-[acetyl(methyl)amino]ethyl phosphate
1.1.1.267 0.00017
-
 pH 7.5, 37°C, recombinant His-tagged enzyme Escherichia coli [4-(hydroxyamino)-4-oxobutyl]phosphonic acid
1.1.1.267 0.000233
-
 pH 7.5, 37°C, recombinant His-tagged enzyme Mycolicibacterium smegmatis 3-[hydroxy(methyl)amino]-3-oxopropyl phosphate
1.1.1.267 0.000279
-
 pH 7.5, 37°C, recombinant His-tagged enzyme Mycolicibacterium smegmatis 2-[acetyl(methyl)amino]ethyl phosphate
1.1.1.267 0.00032
-
 pH 7.5, 37°C, recombinant His-tagged enzyme Mycolicibacterium smegmatis FR-900098
1.1.1.267 0.000342
-
 pH 7.5, 37°C, recombinant His-tagged enzyme Escherichia coli fosfoxacin
1.1.1.267 0.00041
-
 pH 7.5, 37°C, recombinant His-tagged enzyme Mycolicibacterium smegmatis [4-[hydroxy(methyl)amino]-4-oxobutyl]phosphonic acid
1.1.1.267 0.00051
-
 pH 7.5, 37°C, recombinant His-tagged enzyme Mycolicibacterium smegmatis fosmidomycin
1.1.1.267 0.00148
-
 pH 7.5, 37°C, recombinant His-tagged enzyme Mycolicibacterium smegmatis [4-(hydroxyamino)-4-oxobutyl]phosphonic acid
1.1.1.267 0.0021
-
 pH 7.5, 37°C, recombinant His-tagged enzyme Mycolicibacterium smegmatis fosfoxacin
1.1.1.267 0.0026
-
 pH 7.5, 37°C, recombinant His-tagged enzyme Escherichia coli 3-(hydroxyamino)-3-oxopropyl phosphate
1.1.1.267 0.0092
-
 pH 7.5, 37°C, recombinant His-tagged enzyme Mycolicibacterium smegmatis 3-(hydroxyamino)-3-oxopropyl phosphate

General Information

EC Number General Information Comment Organism
1.1.1.267 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
1.1.1.267 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