Information on EC 2.5.1.74 - 1,4-dihydroxy-2-naphthoate polyprenyltransferase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
2.5.1.74
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RECOMMENDED NAME
GeneOntology No.
1,4-dihydroxy-2-naphthoate polyprenyltransferase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
an all-trans-polyprenyl diphosphate + 1,4-dihydroxy-2-naphthoate = a demethylmenaquinol + diphosphate + CO2
show the reaction diagram
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
demethylmenaquinol-6 biosynthesis I
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demethylmenaquinol-8 biosynthesis I
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demethylmenaquinol-9 biosynthesis
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menaquinol-10 biosynthesis
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menaquinol-11 biosynthesis
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menaquinol-12 biosynthesis
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menaquinol-13 biosynthesis
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menaquinol-7 biosynthesis
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vitamin K metabolism
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Ubiquinone and other terpenoid-quinone biosynthesis
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Metabolic pathways
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Biosynthesis of secondary metabolites
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SYSTEMATIC NAME
IUBMB Comments
all-trans-polyprenyl diphosphate:1,4-dihydroxy-2-naphthoate polyprenyltransferase
This enzyme catalyses a step in the synthesis of menaquinone, in which the prenyl chain synthesized by polyprenyl diphosphate synthase is transferred to 1,4-dihydroxy-2-naphthoate (DHNA). The bacterial enzyme is an inner membrane protein [1], with the C-terminus located in the periplasm [3]. It is highly specific for DHNA but not for a specific length of the prenyl chain [2].
CAS REGISTRY NUMBER
COMMENTARY hide
60063-82-3
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
all-trans-nonaprenyl diphosphate + 1,4-dihydroxy-2-naphthoate + H+
demethylmenaquinol-9 + diphosphate + CO2
show the reaction diagram
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all-trans-nonaprenyl diphosphate = solanesyl pyrophosphate
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?
farnesyl diphosphate + 1,4-dihydroxy-2-naphthoate
? + phosphate + CO2
show the reaction diagram
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?
farnesyl diphosphate + 1,4-dihydroxy-2-naphthoate
demethylmenaquinone-3 + phosphate + CO2
show the reaction diagram
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?
farnesyl diphosphate + 1,4-dihydroxy-3-methyl-2-naphthoate
methylmenaquinone-3 + phosphate + CO2
show the reaction diagram
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?
farnesyl diphosphate + 1-hydroxy-2-naphthoate
2-farnesyl-1-naphthol + phosphate + CO2
show the reaction diagram
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?
farnesyl diphosphate + 2-carboxy-4-hydroxy-alpha-tetralone
demethylmenaquinone-3 + phosphate + CO2
show the reaction diagram
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?
solanesyl diphosphate + 1,4-dihydroxy-2-naphthoate
demethylmenaquinone + phosphate + CO2
show the reaction diagram
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?
additional information
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Mn2+
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activation, less efficient than Mg2+
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(R)-1-(4-((3-((4-chlorophenyl)(methoxyimino)methyl)phenoxy)-methyl)piperidin-1-yl)octan-2-yl carbamate
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MIC value for Mycobacterium tuberculosis 0.0023 mg/ml
(R)-1-(4-((3-(4-chlorobenzoyl)phenoxy)methyl)piperidin-1-yl)-octan-2-yl carbamate
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MIC value for Mycobacterium tuberculosis 0.0023 mg/ml
(S)-(2-chloro-4-((1-(2-hydroxyoctyl)piperidin-4-yl)methoxy)-phenyl)(4-chlorophenyl)methanone
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MIC value for Mycobacterium tuberculosis 0.0015 mg/ml
(S)-1-(4-((3-chloro-4-((4-chlorophenyl)(methoxyimino)methyl)-phenoxy)methyl)piperidin-1-yl)octan-2-yl carbamate
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MIC value for Mycobacterium tuberculosis 0.0015 mg/ml
(S)-1-(4-((3-chloro-4-(4-chlorobenzoyl)phenoxy)methyl)-piperidin-1-yl)octan-2-yl carbamate
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MIC value for Mycobacterium tuberculosis 0.0015 mg/ml
EDTA
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maximal activity at 5 mM, inhibition by 20 mM. Mg2+ reactivates
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
EDTA
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maximal activity at 5 mM, inhibition by 20 mM
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0012
(R)-1-(4-((3-((4-chlorophenyl)(methoxyimino)methyl)phenoxy)-methyl)piperidin-1-yl)octan-2-yl carbamate
Mycobacterium tuberculosis
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pH 8.0, 37C
0.0015
(R)-1-(4-((3-(4-chlorobenzoyl)phenoxy)methyl)piperidin-1-yl)-octan-2-yl carbamate
Mycobacterium tuberculosis
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pH 8.0, 37C
0.0035
(S)-(2-chloro-4-((1-(2-hydroxyoctyl)piperidin-4-yl)methoxy)-phenyl)(4-chlorophenyl)methanone
Mycobacterium tuberculosis
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pH 8.0, 37C
0.0015
(S)-1-(4-((3-chloro-4-((4-chlorophenyl)(methoxyimino)methyl)-phenoxy)methyl)piperidin-1-yl)octan-2-yl carbamate
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
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