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

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The expected taxonomic range for this enzyme is: Bacteria, Eukaryota

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
Biosynthesis of secondary metabolites
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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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Metabolic pathways
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Ubiquinone and other terpenoid-quinone biosynthesis
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vitamin K metabolism
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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
gene McMenA
UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
the enzyme catalyzes the conversion of 1,4-dihydroxy-2-naphthoate to demethylmenaquinone. This step, prior to the methylation of demethylmenaquinone to menaquinone (vitamin K2), is a key reaction in menaquinone biosynthesis. Menaquinone is an obligatory component of the electron transfer pathway. Enzyme McMenA plays a role in the biosynthesis of cantharidin and ATP in Mylabris cichorii
additional information
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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?
octaprenyl diphosphate + 1,4-dihydroxy-2-naphthoate
a demethylmenaquinol + diphosphate + 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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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
octaprenyl diphosphate + 1,4-dihydroxy-2-naphthoate
a demethylmenaquinol + diphosphate + CO2
show the reaction diagram
A0A0U1XZ37
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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
Mycobacterium tuberculosis
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pH 8.0, 37C
0.0015
(S)-1-(4-((3-chloro-4-(4-chlorobenzoyl)phenoxy)methyl)-piperidin-1-yl)octan-2-yl carbamate
Mycobacterium tuberculosis
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pH 8.0, 37C
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
8.94
sequence calculation
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
lowest expression level of MenA
Manually annotated by BRENDA team
highest expression level of MenA
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
x * 37900, about, sequence calculation
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
gene McMenA, DNA and amino acid sequence determination and analysis, sequence comparison and phylogenetic analysis, quantitative RT-PCR enzyme expression analysis
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
Show AA Sequence (5103 entries)
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