Information on EC 1.14.13.38 - anhydrotetracycline 6-monooxygenase

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The expected taxonomic range for this enzyme is: Streptomyces

EC NUMBER
COMMENTARY hide
1.14.13.38
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RECOMMENDED NAME
GeneOntology No.
anhydrotetracycline 6-monooxygenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
anhydrotetracycline + NADPH + H+ + O2 = 12-dehydrotetracycline + NADP+ + H2O
show the reaction diagram
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
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redox reaction
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-
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reduction
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Biosynthesis of antibiotics
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Biosynthesis of type II polyketide products
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tetracycline and oxytetracycline biosynthesis
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Tetracycline biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
anhydrotetracycline,NADPH:oxygen oxidoreductase (6-hydroxylating)
The enzyme, characterized from the bacterium Streptomyces rimosus, participates in the biosynthesis of tetracycline antibiotics. It can also catalyse EC 1.14.13.234, 12-dehydrotetracycline 5-monooxygenase.
CAS REGISTRY NUMBER
COMMENTARY hide
70766-62-0
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
high- and low-production strain
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Manually annotated by BRENDA team
gene otcC, strain R6-500
SwissProt
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
anhydrooxytetracycline + NADPH + O2
?
show the reaction diagram
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-
-
-
?
anhydrotetracycline + NADPH + O2
12-dehydrotetracycline + NADP+ + H2O
show the reaction diagram
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
anhydrotetracycline + NADPH + O2
12-dehydrotetracycline + NADP+ + H2O
show the reaction diagram
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
ascorbate
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increase of activity
NADPH
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Ca2+
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increase of activity at 0.1-2 mM
Co2+
-
increase of activity
Cu2+
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increase of activity
Fe2+
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increase of activity
Fe3+
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increase of activity
Mg2+
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increase of activity at 0.1-1 mM
Mn2+
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increase of activity
Ni2+
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increase of activity
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
ammonium sulfate
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Ca2+
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above 2 mM
chlortetracycline
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dithiobis-(2-nitrobenzoic acid)
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40% inhibition at 1 mM, irreversible
iodoacetamide
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14% inhibition at 1 mM, irreversible
Mg2+
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above 1 mM
N-ethylmaleimide
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complete inhibition at 0.1 M, irreversible
oxytetracycline
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
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addition of supernatant of Streptomyces aureofaciens or Streptomyces rimosus crude extract after boiling and centrifugation increases activity 7fold
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.022
anhydrotetracycline
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.0000112
recombinant wild-type enzyme in Escherichia coli cell extract
0.00264
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low production strain, membrane fraction
0.0078
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high production strain, cytoplasm
additional information
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overview: different activities in various subcellular fractions
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
29 - 30
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assay at
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
57500
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2 * 57500, SDS-PAGE
115000
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gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
dimer
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2 * 57500, SDS-PAGE
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
loss of activity during purification
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-25°C, crude extract stable for several weeks
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4°C, crude extract stable for several days
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
gene otcC, DNA and amino acid sequence determination and analysis, expression of the glycine mutant enzyme in Escherichia coli strain BL21(DE3)
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pharmacology
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synthesis of chlortetracycline