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Information on EC 1.14.13.215 - protoasukamycin 4-monooxygenase
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The expected taxonomic range for this enzyme is: Streptomyces nodosus
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EC NUMBER 
COMMENTARY 
1.14.13.215
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RECOMMENDED NAME
GeneOntology No.
protoasukamycin 4-monooxygenase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
protoasukamycin + NADH + H+ + O2 = 4-hydroxyprotoasukamycin + NAD+ + H2O
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SYSTEMATIC NAME
IUBMB Comments
protoasukamycin,NADH:oxygen oxidoreductase (4-hydroxylating)
The enzyme, characterized from the bacterium Streptomyces nodosus subsp. asukaensis, is involved in the biosynthesis of the antibiotic asukamycin. Requires a flavin cofactor, with no preference among FMN, FAD or riboflavin. When flavin concentration is low, activity is enhanced by the presence of the NADH-dependent flavin-reductase AsuE2.
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
evolution
malfunction
metabolism
evolution
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enzyme AsuE1 belongs to the family of single-component monooxygenases: a single enzyme catalyzes both the reduction of flavin by NADPH, and the hydroxylation using molecular oxygen and reduced flavin cofactor
evolution
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enzyme AsuE1 belongs to the family of single-component monooxygenases: a single enzyme catalyzes both the reduction of flavin by NADPH, and the hydroxylation using molecular oxygen and reduced flavin cofactor
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malfunction
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disruption of asuE2 significantly decreases the yield of asukamycin and results in the accumulation of protoasukamycin
malfunction
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disruption of asuE2 significantly decreases the yield of asukamycin and results in the accumulation of protoasukamycin
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metabolism
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AsuE1 and AsuE3, both single-component flavin-dependent monooxygenases, catalyze the exquisite regio- and enantiospecific postpolyketide synthase (PKS) assembly oxygenations. AsuE1 installs a hydroxyl group on the 3,4-AHB ring to form a 4-hydroxyquinone moiety, which is epoxidized by AsuE3 to yield the epoxyquinone functionality. Despite being a single-component monooxygenase, AsuE1 activity is elicited by AsuE2, a pathway-specific flavin reductase
metabolism
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in the asukamycin metabolism, enzymes AsuE1 and AsuE2 catalyze the conversion of protoasukamycin to 4-hydroxyprotoasukamycin, which is epoxidized at C5-C6 by enzyme AsuE3 to the final product, asukamycin. Synthesis and structures of asukamycin and related metabolites, overview
metabolism
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AsuE1 and AsuE3, both single-component flavin-dependent monooxygenases, catalyze the exquisite regio- and enantiospecific postpolyketide synthase (PKS) assembly oxygenations. AsuE1 installs a hydroxyl group on the 3,4-AHB ring to form a 4-hydroxyquinone moiety, which is epoxidized by AsuE3 to yield the epoxyquinone functionality. Despite being a single-component monooxygenase, AsuE1 activity is elicited by AsuE2, a pathway-specific flavin reductase
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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
protoasukamycin + NADH + H+ + O2
4-hydroxyprotoasukamycin + NAD+ + H2O
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?
protoasukamycin + NADH + H+ + O2
4-hydroxyprotoasukamycin + NAD+ + H2O
enzyme AsuE1 is a flavin-dependent protoasukamycin hydroxylase, that belongs to the family of single-component monooxygenases: a single enzyme catalyzes both the reduction of flavin by NADPH, and the hydroxylation using molecular oxygen and reduced flavin cofactor
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-
?
protoasukamycin + NADH + H+ + O2
4-hydroxyprotoasukamycin + NAD+ + H2O
NADH is the preferred cofactor, it reduces the flavin that gets oxidized in the hydroxylation of protoasukamycin, reaction chain overview
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?
protoasukamycin + NADH + H+ + O2
4-hydroxyprotoasukamycin + NAD+ + H2O
enzyme AsuE1 is a flavin-dependent protoasukamycin hydroxylase, that belongs to the family of single-component monooxygenases: a single enzyme catalyzes both the reduction of flavin by NADPH, and the hydroxylation using molecular oxygen and reduced flavin cofactor
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-
?
protoasukamycin + NADH + H+ + O2
4-hydroxyprotoasukamycin + NAD+ + H2O
NADH is the preferred cofactor, it reduces the flavin that gets oxidized in the hydroxylation of protoasukamycin, reaction chain overview
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?
protoasukamycin + NADPH + H+ + O2
4-hydroxyprotoasukamycin + NADP+ + H2O
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?
protoasukamycin + NADPH + H+ + O2
4-hydroxyprotoasukamycin + NADP+ + H2O
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?
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NATURAL SUBSTRATES
NATURAL PRODUCTS
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
protoasukamycin + NADH + H+ + O2
4-hydroxyprotoasukamycin + NAD+ + H2O
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-
-
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?
protoasukamycin + NADH + H+ + O2
4-hydroxyprotoasukamycin + NAD+ + H2O
D7P5V0
enzyme AsuE1 is a flavin-dependent protoasukamycin hydroxylase, that belongs to the family of single-component monooxygenases: a single enzyme catalyzes both the reduction of flavin by NADPH, and the hydroxylation using molecular oxygen and reduced flavin cofactor
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-
?
protoasukamycin + NADH + H+ + O2
4-hydroxyprotoasukamycin + NAD+ + H2O
D7P5V0
enzyme AsuE1 is a flavin-dependent protoasukamycin hydroxylase, that belongs to the family of single-component monooxygenases: a single enzyme catalyzes both the reduction of flavin by NADPH, and the hydroxylation using molecular oxygen and reduced flavin cofactor
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
FMN
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enzyme AsuE2 contains a trace amount of FMN at a molar ratio of 1:2000 (FMN:AsuE2) upon purification from Escherichia coli
additional information
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enzyme AsuE1 is a flavin-dependent protoasukamycin hydroxylase, that displays no significant preference toward flavin cofactors, because FAD, FMN, and riboflavin are utilized efficiently in the catalysis
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
protein AsuE2
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despite being a single-component monooxygenase, AsuE1 activity is enhanced by AsuE2, a pathway-specific flavin reductase, UniProt-ID D7P5W0, AsuE2 is encoded in the asu gene cluster. Enzyme AsuE2 might assist the catalysis of AsuE1 by providing a reduced form of flavin in Streptomyces nodosus
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protein AsuE2
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endogenous protein AsuE2, UniProt-ID D7P5W0, is necessary for the full catalytic function of AsuE1 as a two-component flavoprotein hydroxylase. AsuE2 is a homologue of the flavin reductase PheA2, which recycles oxidized FADox and provides FADred to its hydroxylase partner PheA1 in the phenol hydroxylation in Bacillus thermoglucosidasius A7
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0123
NADH
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in presence of 0.01 mM FAD, recombinant enzyme, pH 7.0, 30°C
1.84
NADPH
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in presence of 0.01 mM FAD, recombinant enzyme, pH 7.0, 30°C
0.0213
protoasukamycin
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in presence of 0.01 mM FAD, recombinant enzyme, pH 7.0, 30°C
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.113
NADH
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in presence of 0.01 mM FAD, recombinant enzyme, pH 7.0, 30°C
0.324
NADPH
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in presence of 0.01 mM FAD, recombinant enzyme, pH 7.0, 30°C
16.67
protoasukamycin
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in presence of 0.01 mM FAD, recombinant enzyme, pH 7.0, 30°C
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
recombinant His-tagged enzyme from Escherichia coli strain BL21(DE3) by nickel affinity chomatography
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
cloning of asukamycin biosynthetic gene cluster, including gene asuE1 encoding the enzyme, recombinant expression in Escherichia coli strain BW25113/pIJ790, heterologous expression of the complete gene cluster in the asukamycin-nonproducing Streptomyces lividans strain K4-114
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gene asuE1, recombinant expression of His-tagged enzyme in Escherichia coli strain BL21(DE3)
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LINKS TO OTHER DATABASES (specific for EC-Number 1.14.13.215)
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