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Information on EC 1.1.98.3 - decaprenylphospho-beta-D-ribofuranose 2-dehydrogenase and Organism(s) Mycolicibacterium smegmatis and UniProt Accession A0R607
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1.1.98.3 decaprenylphospho-beta-D-ribofuranose 2-dehydrogenaseIUBMB Comments
The enzyme, isolated from the bacterium Mycobacterium smegmatis, is involved, along with EC 1.1.1.333, decaprenylphospho-D-erythro-pentofuranosid-2-ulose 2-reductase, in the epimerization of trans,octacis-decaprenylphospho-beta-D-ribofuranose to trans,octacis-decaprenylphospho-beta-D-arabinofuranose, the arabinosyl donor for the biosynthesis of mycobacterial cell wall arabinan polymers.
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Word Map
- 1.1.98.3
- tuberculosis
- mycobacterium
-
antitubercular
-
benzothiazinones
-
antimycobacterial
-
antituberculosis
- pbtz169
- arabinans
- arabinogalactan
-
anti-tb
- corynebacterineae
-
drug-susceptible
-
xdr-tb
-
1,2,3-triazole
- tca1
-
dinitrobenzamides
-
nitroso
- analysis
The taxonomic range for the selected organisms is: Mycolicibacterium smegmatis
The enzyme appears in selected viruses and cellular organisms
The enzyme appears in selected viruses and cellular organisms
Reaction Schemes
Synonyms
dpre1, decaprenylphosphoryl-beta-d-ribose 2'-epimerase, decaprenylphosphoryl-d-ribose oxidase, rv3790, decaprenylphospho-beta-d-ribofuranose 2-oxidase, msmeg_6382, decaprenylphosphoryl-beta-d-ribose 2-epimerase, 
more
topSYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
decaprenylphospho-beta-D-ribofuranose 2-oxidase
-
-
-
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decaprenylphosphoryl-beta-D-ribofuranose 2'-epimerase
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-
-
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DprE1
Rv3790
DprE1
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-
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-
Rv3790
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PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
trans,octacis-decaprenylphospho-beta-D-ribofuranose:FAD 2-oxidoreductase
The enzyme, isolated from the bacterium Mycobacterium smegmatis, is involved, along with EC 1.1.1.333, decaprenylphospho-D-erythro-pentofuranosid-2-ulose 2-reductase, in the epimerization of trans,octacis-decaprenylphospho-beta-D-ribofuranose to trans,octacis-decaprenylphospho-beta-D-arabinofuranose, the arabinosyl donor for the biosynthesis of mycobacterial cell wall arabinan polymers.
SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(2Z,6E)-farnesylphosphoryl-beta-D-ribofuranose + FAD
(2Z,6E)-farnesylphosphoryl-D-beta-D-erythro-pentofuranosid-2-ulose + FADH2
-
oxidation reaction calyzed by decaprenylphospho-beta-D-ribofuranose 2-oxidase DprE1
-
?
trans,octacis-decaprenylphospho-beta-D-ribofuranose + FAD
trans,octacis-decaprenylphospho-beta-D-erythro-pentofuranosid-2-ulose + FADH2
trans,octacis-decaprenylphospho-beta-D-ribofuranose + FAD
trans,octacis-decaprenylphospho-beta-D-erythro-pentofuranosid-2-ulose + FADH2
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-
-
?
additional information
?
-
decaprenylphosphoryl-beta-D-ribofuranose 2'-epimerase is constituted of decaprenylphospho-beta-D-ribofuranose 2-oxidase DprE1 and decaprenylphospho-beta-D-erythro-pentofuranosid-2-ulose 2-reductase DprE2 that together catalyze the epimerization of decaprenylphosphoryl-beta-D-ribofuranose to decaprenylphosphoryl-beta-D-arabinofuranose
-
-
?
trans,octacis-decaprenylphospho-beta-D-ribofuranose + FAD
trans,octacis-decaprenylphospho-beta-D-erythro-pentofuranosid-2-ulose + FADH2
-
-
-
?
trans,octacis-decaprenylphospho-beta-D-ribofuranose + FAD
trans,octacis-decaprenylphospho-beta-D-erythro-pentofuranosid-2-ulose + FADH2
-
oxidation reaction catalyzed by decaprenylphospho-beta-D-ribofuranose 2-oxidase DprE1
-
?
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
trans,octacis-decaprenylphospho-beta-D-ribofuranose + FAD
trans,octacis-decaprenylphospho-beta-D-erythro-pentofuranosid-2-ulose + FADH2
-
-
-
?
trans,octacis-decaprenylphospho-beta-D-ribofuranose + FAD
trans,octacis-decaprenylphospho-beta-D-erythro-pentofuranosid-2-ulose + FADH2
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-
-
?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
2-[(2S)-2-methyl-1,4-dioxa-8-azaspiro[4.5]dec-8-yl]-8-nitro-6-(trifluoromethyl)-4H-1,3-benzothiazin-4-one
i.e. BTZ043, inhibits enzyme by formation of a semimercaptal
1,3-dimethyl-5-((3-(trifluoromethyl)benzylamino)methyl)-1Hpyrazolo[3,4-b]pyridin-6(7H)-one
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1-(6-methoxy-3-methyl-1-phenyl-1H-pyrazolo[3,4-b]pyridin-5-yl)-N-(3-(trifluoromethyl)benzyl)methanamine
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2-[(2S)-2-methyl-1,4-dioxa-8-azaspiro[4.5]decan-8-yl]-8-nitro-6-(trifluoromethyl)-4H-1,3-benzothiazin-4-one
BTZ043
2-[4-(cyclohexylmethyl)piperazin-1-yl]-8-nitro-6-(trifluoromethyl)-4H-1,3-benzothiazin-4-one
PBTZ169
3,7-dimethyl-1-phenyl-5-((3-(trifluoromethyl)benzylamino)-methyl)-1H-pyrazolo[3,4-b]pyridin-6(7H)-one
-
3-(((3-methyl-6-oxo-1-phenyl-6,7-dihydro-1H-pyrazolo[3,4-b]-pyridin-5-yl)methylamino)methyl)benzonitrile
-
3-cyclopropyl-1-phenyl-5-(((6-(trifluoromethyl)pyridin-2-yl)-methylamino)methyl)-1H-pyrazolo[3,4-b]pyridin-6(7H)-one
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3-cyclopropyl-1-phenyl-5-((3-(trifluoromethyl)benzylamino)-methyl)-1H-pyrazolo[3,4-b]pyridin-6(7H)-one
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3-cyclopropyl-5-(((3-methyl-6-(trifluoromethyl)pyridin-2-yl)-methylamino)methyl)-1-phenyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one
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3-cyclopropyl-5-((2-fluoro-3-(trifluoromethyl)benzylamino)-methyl)-1-phenyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one
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3-cyclopropyl-5-((2-fluoro-5-(trifluoromethyl)benzylamino)-methyl)-1-phenyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one
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3-cyclopropyl-5-((2-methyl-5-(trifluoromethyl)benzylamino)-methyl)-1-phenyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one
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3-isopropyl-5-((2-methyl-5-(trifluoromethyl)benzylamino)-methyl)-1-phenyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one
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3-methyl-1-(pyridin-2-yl)-5-((3-(trifluoromethyl)benzylamino)-methyl)-1H-pyrazolo[3,4-b]pyridin-6(7H)-one
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3-methyl-1-p-tolyl-5-((3-(trifluoromethyl)benzylamino)methyl)-1H-pyrazolo[3,4-b]pyridin-6(7H)-one
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3-methyl-1-phenyl-5-((3-(trifluoromethyl)benzylamino)methyl)-1H-pyrazolo[3,4-b]pyridin-6(7H)-one
-
3-methyl-1-phenyl-5-((7-(trifluoromethyl)-3,4-dihydroisoquinolin-2(1H)-yl)methyl)-1H-pyrazolo[3,4-b]pyridin-6(7H)-one
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3-methyl-5-((2-methyl-5-(trifluoromethyl)benzylamino)methyl)-1-phenyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one
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3-methyl-5-((3-methylbenzylamino)methyl)-1-phenyl-1Hpyrazolo[3,4-b]pyridin-6(7H)-one
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3-methyl-5-((methyl(3-(trifluoromethyl)benzyl)amino)methyl)-1-phenyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one
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3-methyl-6-oxo-1-phenyl-N-(3-(trifluoromethyl)benzyl)-6,7-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carboxamide
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5-((3,4-dimethylbenzylamino)methyl)-3-methyl-1-phenyl-1Hpyrazolo[3,4-b]pyridin-6(7H)-one
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5-((3-fluorobenzylamino)methyl)-3-methyl-1-phenyl-1Hpyrazolo[3,4-b]pyridin-6(7H)-one
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5-((benzylamino)methyl)-3-methyl-1-phenyl-1H-pyrazolo[3,4-b]-pyridin-6(7H)-one
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ethyl {2-[(1,3-benzothiazole-2-carbonyl)amino]thiophene-3-carbonyl}carbamate
TCA1
N-(2-fluoroethyl)-1-[(6-methoxy-5-methylpyrimidin-4-yl)methyl]-1H-pyrrolo[3,2-b]pyridine-3-carboxamide
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additional information
benzothiazinone and dinitrobenzamide inhibitors target decaprenylphospho-beta-D-ribofuranose 2-oxidase DprE1. Several mutants showing high levels of dinitrobenzamide resistance, exhibit a mutation in residue Cys394 of DprE1
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additional information
-
benzothiazinone and dinitrobenzamide inhibitors target decaprenylphospho-beta-D-ribofuranose 2-oxidase DprE1. Several mutants showing high levels of dinitrobenzamide resistance, exhibit a mutation in residue Cys394 of DprE1
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IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.1
1,3-dimethyl-5-((3-(trifluoromethyl)benzylamino)methyl)-1Hpyrazolo[3,4-b]pyridin-6(7H)-one
Mycolicibacterium smegmatis
IC50 above 0.1 mM, pH and temperature not specified in the publication
0.01
1-(6-methoxy-3-methyl-1-phenyl-1H-pyrazolo[3,4-b]pyridin-5-yl)-N-(3-(trifluoromethyl)benzyl)methanamine
Mycolicibacterium smegmatis
IC50 above 0.01 mM, pH and temperature not specified in the publication
0.01
3,7-dimethyl-1-phenyl-5-((3-(trifluoromethyl)benzylamino)-methyl)-1H-pyrazolo[3,4-b]pyridin-6(7H)-one
Mycolicibacterium smegmatis
IC50 above 0.01 mM, pH and temperature not specified in the publication
0.0026
3-(((3-methyl-6-oxo-1-phenyl-6,7-dihydro-1H-pyrazolo[3,4-b]-pyridin-5-yl)methylamino)methyl)benzonitrile
Mycolicibacterium smegmatis
pH and temperature not specified in the publication
0.0005
3-cyclopropyl-1-phenyl-5-(((6-(trifluoromethyl)pyridin-2-yl)-methylamino)methyl)-1H-pyrazolo[3,4-b]pyridin-6(7H)-one
Mycolicibacterium smegmatis
pH and temperature not specified in the publication
0.00004
3-cyclopropyl-1-phenyl-5-((3-(trifluoromethyl)benzylamino)-methyl)-1H-pyrazolo[3,4-b]pyridin-6(7H)-one
Mycolicibacterium smegmatis
pH and temperature not specified in the publication
0.00001
3-cyclopropyl-5-(((3-methyl-6-(trifluoromethyl)pyridin-2-yl)-methylamino)methyl)-1-phenyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one
Mycolicibacterium smegmatis
pH and temperature not specified in the publication
0.000005
3-cyclopropyl-5-((2-fluoro-3-(trifluoromethyl)benzylamino)-methyl)-1-phenyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one
Mycolicibacterium smegmatis
pH and temperature not specified in the publication
0.00007
3-cyclopropyl-5-((2-fluoro-5-(trifluoromethyl)benzylamino)-methyl)-1-phenyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one
Mycolicibacterium smegmatis
pH and temperature not specified in the publication
0.00001
3-cyclopropyl-5-((2-methyl-5-(trifluoromethyl)benzylamino)-methyl)-1-phenyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one
Mycolicibacterium smegmatis
pH and temperature not specified in the publication
0.000005
3-isopropyl-5-((2-methyl-5-(trifluoromethyl)benzylamino)-methyl)-1-phenyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one
Mycolicibacterium smegmatis
pH and temperature not specified in the publication
0.0006
3-methyl-1-p-tolyl-5-((3-(trifluoromethyl)benzylamino)methyl)-1H-pyrazolo[3,4-b]pyridin-6(7H)-one
Mycolicibacterium smegmatis
pH and temperature not specified in the publication
0.0004
3-methyl-1-phenyl-5-((3-(trifluoromethyl)benzylamino)methyl)-1H-pyrazolo[3,4-b]pyridin-6(7H)-one
Mycolicibacterium smegmatis
pH and temperature not specified in the publication
0.0062
3-methyl-1-phenyl-5-((7-(trifluoromethyl)-3,4-dihydroisoquinolin-2(1H)-yl)methyl)-1H-pyrazolo[3,4-b]pyridin-6(7H)-one
Mycolicibacterium smegmatis
pH and temperature not specified in the publication
0.000007
3-methyl-5-((2-methyl-5-(trifluoromethyl)benzylamino)methyl)-1-phenyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one
Mycolicibacterium smegmatis
pH and temperature not specified in the publication
0.0028
3-methyl-5-((3-methylbenzylamino)methyl)-1-phenyl-1Hpyrazolo[3,4-b]pyridin-6(7H)-one
Mycolicibacterium smegmatis
pH and temperature not specified in the publication
0.00006
3-methyl-5-((methyl(3-(trifluoromethyl)benzyl)amino)methyl)-1-phenyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one
Mycolicibacterium smegmatis
pH and temperature not specified in the publication
0.001
3-methyl-6-oxo-1-phenyl-N-(3-(trifluoromethyl)benzyl)-6,7-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carboxamide
Mycolicibacterium smegmatis
pH and temperature not specified in the publication
0.0012
5-((3,4-dimethylbenzylamino)methyl)-3-methyl-1-phenyl-1Hpyrazolo[3,4-b]pyridin-6(7H)-one
Mycolicibacterium smegmatis
pH and temperature not specified in the publication
0.002
5-((3-fluorobenzylamino)methyl)-3-methyl-1-phenyl-1Hpyrazolo[3,4-b]pyridin-6(7H)-one
Mycolicibacterium smegmatis
pH and temperature not specified in the publication
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
physiological function
physiological function
construction of a conditional gene knockout strain targeting the gene encoding subunit dprE1 of decaprenylphosphoribose 2' epimerase. The gene is essential for viability, results suggests that decaprenylphosphoryl arabinose synthesis is essential in mycobacteria, indicate a lack of redundancy in decaprenylphosphoryl arabinose synthesis and suggest that no alternative arabinose donors for cell wall biosynthesis exist
physiological function
decaprenylphosphoryl-beta-D-ribofuranose 2'-epimerase is constituted of DprE1 and DprE2 that together catalyze the epimerization of decaprenylphosphoryl-beta-D-ribofuranose to decaprenylphosphoryl-beta-D-arabinofuranose
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
sitting drop vapor diffusion method, using 15-20% (v/v) isopropanol, 0.2 M sodium citrate pH 6.8, and 0.5% (w/v) N,N-dimethyldodecylamine-N-oxide
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
C394G
benzothiazinone-resistant mutant, reduces benzothiazinones to inert metabolites while avoiding covalent inactivation
C394S
benzothiazinone-resistant mutant, reduces benzothiazinones to inert metabolites while avoiding covalent inactivation
additional information
additional information
isolation of mutant strains resistant to dinitrobenzamides. All mutants show cross-resistance to benzothiazinones and dinitrobenzamides, and all the mutant strains with a higher level of resistance to dinitrobenzamides have a substitution C394G of MSMEG_6382 gene encoding decaprenylphospho-?-D-ribofuranose 2-oxidase
additional information
-
isolation of mutant strains resistant to dinitrobenzamides. All mutants show cross-resistance to benzothiazinones and dinitrobenzamides, and all the mutant strains with a higher level of resistance to dinitrobenzamides have a substitution C394G of MSMEG_6382 gene encoding decaprenylphospho-?-D-ribofuranose 2-oxidase
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Trefzer, C.; Skovierova, H.; Buroni, S.; Bobovska, A.; Nenci, S.; Molteni, E.; Pojer, F.; Pasca, M.; Makarov, V.; Cole, S.; Riccardi, G.; Mikusova, K.; Johnsson, K.
Benzothiazinones are suicide inhibitors of mycobacterial decaprenylphosphoryl-beta-D-ribofuranose 2'-oxidase DprE1
J. Am. Chem. Soc.
134
912-915
2012
Mycolicibacterium smegmatis (A0R607)
Crellin, P.K.; Brammananth, R.; Coppel, R.L.
Decaprenylphosphoryl-beta-D-ribose 2-epimerase, the target of benzothiazinones and dinitrobenzamides, is an essential enzyme in Mycobacterium smegmatis
PLoS ONE
6
e16869
2011
Mycolicibacterium smegmatis (A0R607), Mycolicibacterium smegmatis
Ribeiro, A.L.; Degiacomi, G.; Ewann, F.; Buroni, S.; Incandela, M.L.; Chiarelli, L.R.; Mori, G.; Kim, J.; Contreras-Dominguez, M.; Park, Y.S.; Han, S.J.; Brodin, P.; Valentini, G.; Rizzi, M.; Riccardi, G.; Pasca, M.R.
Analogous mechanisms of resistance to benzothiazinones and dinitrobenzamides in Mycobacterium smegmatis
PLoS ONE
6
e26675
2011
Mycolicibacterium smegmatis (A0R607), Mycolicibacterium smegmatis
Panda, M.; Ramachandran, S.; Ramachandran, V.; Shirude, P.S.; Humnabadkar, V.; Nagalapur, K.; Sharma, S.; Kaur, P.; Guptha, S.; Narayan, A.; Mahadevaswamy, J.; Ambady, A.; Hegde, N.; Rudrapatna, S.S.; Hosagrahara, V.P.; Sambandamurthy, V.K.; Raichurkar, A.
Discovery of pyrazolopyridones as a novel class of noncovalent DprE1 inhibitor with potent anti-mycobacterial activity
J. Med. Chem.
57
4761-4771
2014
Mycobacterium tuberculosis (P9WJF1), Mycobacterium tuberculosis, Mycobacterium tuberculosis H37Rv (P9WJF1), Mycolicibacterium smegmatis (P9WJF1)
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