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EC Tree
IUBMB Comments 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.
The enzyme appears in viruses and cellular organisms
Synonyms
anhydrotetracycline oxygenase, anhydrotetracycline monooxygenase,
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anhydrotetracycline monooxygenase
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ambiguous
anhydrotetracycline oxygenase
oxygenase, anhydrotetracycline
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anhydrotetracycline oxygenase
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anhydrotetracycline oxygenase
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anhydrotetracycline + NADPH + H+ + O2 = 12-dehydrotetracycline + NADP+ + H2O
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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.
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anhydrooxytetracycline + NADPH + O2
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anhydrotetracycline + NADPH + O2
12-dehydrotetracycline + NADP+ + H2O
anhydrotetracycline + NADPH + O2
12-dehydrotetracycline + NADP+ + H2O
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anhydrotetracycline + NADPH + O2
12-dehydrotetracycline + NADP+ + H2O
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anhydrotetracycline + NADPH + O2
12-dehydrotetracycline + NADP+ + H2O
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anhydrotetracycline + NADPH + O2
12-dehydrotetracycline + NADP+ + H2O
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anhydrotetracycline + NADPH + O2
12-dehydrotetracycline + NADP+ + H2O
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tetracycline and chlortetracycline biosynthetic pathways
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anhydrotetracycline + NADPH + O2
12-dehydrotetracycline + NADP+ + H2O
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chlortetracycline biosynthetic pathway
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anhydrotetracycline + NADPH + O2
12-dehydrotetracycline + NADP+ + H2O
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involved in the biosynthesis of tetracyclines
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anhydrotetracycline + NADPH + O2
12-dehydrotetracycline + NADP+ + H2O
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anhydrotetracycline + NADPH + O2
12-dehydrotetracycline + NADP+ + H2O
the enzyme catalyzes a hydroxylation of the anthracycline structure at position C-6 after biosynthesis of the polyketide backbone is completed, Biosynthesis of oxytetracycline, overview
product identification
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anhydrotetracycline + NADPH + O2
12-dehydrotetracycline + NADP+ + H2O
anhydrotetracycline + NADPH + O2
12-dehydrotetracycline + NADP+ + H2O
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tetracycline and chlortetracycline biosynthetic pathways
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anhydrotetracycline + NADPH + O2
12-dehydrotetracycline + NADP+ + H2O
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chlortetracycline biosynthetic pathway
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anhydrotetracycline + NADPH + O2
12-dehydrotetracycline + NADP+ + H2O
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involved in the biosynthesis of tetracyclines
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anhydrotetracycline + NADPH + O2
12-dehydrotetracycline + NADP+ + H2O
the enzyme catalyzes a hydroxylation of the anthracycline structure at position C-6 after biosynthesis of the polyketide backbone is completed, Biosynthesis of oxytetracycline, overview
product identification
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ascorbate
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increase of activity
NADPH
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NADPH
three essential glycine codons are located within the putative NADPH-binding domain
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Ca2+
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increase of activity at 0.1-2 mM
Co2+
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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
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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
N-ethylmaleimide
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complete inhibition at 0.1 M, irreversible
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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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0.022
anhydrotetracycline
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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
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high- and low-production strain
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brenda
gene otcC, strain R6-500
SwissProt
brenda
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brenda
50/137, UV-light induced mutant of strain 84/25
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brenda
high- and low-production strain
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brenda
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brenda
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predominantly, high-production strain, distribution in the cell is influenced by benzylthiocyanate
brenda
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predominantly, high-production strain, distribution in the cell is influenced by benzylthiocyanate
brenda
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predominantly, low-production strain
brenda
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predominantly, low-production strain
brenda
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57500
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2 * 57500, SDS-PAGE
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dimer
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2 * 57500, SDS-PAGE
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additional information
a otcC disruption mutant strain of Streptomyces rimosus synthesizes a novel C-17 polyketide, the ability to make a 19-carbon backbone in the mutant strain is restored when the inactive mutant enzyme, with three essential glycine residues of the NADH-binding domain mutated by site-directed mutagenesis, is expressed in the disruption mutant strain, thus the quarternary structure of the enzyme is required, not only the its activity, in the synthase complex
additional information
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a otcC disruption mutant strain of Streptomyces rimosus synthesizes a novel C-17 polyketide, the ability to make a 19-carbon backbone in the mutant strain is restored when the inactive mutant enzyme, with three essential glycine residues of the NADH-binding domain mutated by site-directed mutagenesis, is expressed in the disruption mutant strain, thus the quarternary structure of the enzyme is required, not only the its activity, in the synthase complex
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loss of activity during purification
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-25°C, crude extract stable for several weeks
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4°C, crude extract stable for several days
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gene otcC, DNA and amino acid sequence determination and analysis, expression of the glycine mutant enzyme in Escherichia coli strain BL21(DE3)
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pharmacology
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synthesis of chlortetracycline
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Vancurova, I.; Flieger, M.; Volc, J.; Benes, M.J.; Novotna, J.; Neuzil, J.; Behal, V.
Partial purification and characterization of anhydrotetracycline oxygenase of Streptomyces aureofaciens
J. Basic Microbiol.
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529-533
1987
Kitasatospora aureofaciens
brenda
Behal, V.; Neuzil, J.; Hostalek, Z.
Effect of tetracycline derivates and some cations on the activity of anhydrotetracycline oxygenase
Biotechnol. Lett.
5
537-542
1983
Kitasatospora aureofaciens
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brenda
Vancurova, I.; Volc, J.; Flieger, M.; Neuzil, J.; Novotna, J.; Vlach, J.; Behal, V.
Isolation of pure anhydrotetracycline oxygenase from Streptomyces aureofaciens
Biochem. J.
253
263-267
1988
Kitasatospora aureofaciens
brenda
Neuzil, J.; Novotna, J.; Vancurova, I.; Behal, V.; Hostalek, Z.
A direct-injection reversed-phase liquid chromatographic micromethod for studying the kinetics of terminal reactions of tetracycline biosynthesis
Anal. Biochem.
181
125-129
1989
Kitasatospora aureofaciens
brenda
Erban, V.; Trilisenko, L.V.; Novotna, J.; Behal, V.; Kulaev, I.S.; Hostalek, Z.
Subcellular localization if enzymes in Streptomyces areofaciens and its alteration by benzyl thiocyanate
Folia Microbiol. (Praha)
32
411-416
1987
Kitasatospora aureofaciens, Kitasatospora aureofaciens low-production
brenda
Behal, V.; Gregrova-Prusakova, J.; Hostalek, Z.
Effect of inorganic phosphate and benzyl thiocyanate of the activity of anhydrotetracycline oxygenase in Streptomyces aureofaciens
Folia Microbiol. (Praha)
27
102-106
1982
Kitasatospora aureofaciens
brenda
Li, X.M.; Novotna, J.; Vohradsky, J.; Weiser, J.
Major proteins related to chlortetracycline biosynthesis in a Streptomyces aureofaciens production strain studied by quantitative proteomics
Appl. Microbiol. Biotechnol.
57
717-724
2001
Kitasatospora aureofaciens
brenda
Peric-Concha, N.; Borovicka, B.; Long, P.F.; Hranueli, D.; Waterman, P.G.; Hunter, I.S.
Ablation of the otcC gene encoding a post-polyketide hydroxylase from the oxytetracyline biosynthetic pathway in Streptomyces rimosus results in novel polyketides with altered chain length
J. Biol. Chem.
280
37455-37460
2005
Streptomyces rimosus (Q58PK7), Streptomyces rimosus
brenda
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1.14.13.38 anhydrotetracycline 6-monooxygenase
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