Information on EC 1.14.13.180 - aklavinone 12-hydroxylase

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The expected taxonomic range for this enzyme is: Streptomyces

EC NUMBER
COMMENTARY hide
1.14.13.180
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RECOMMENDED NAME
GeneOntology No.
aklavinone 12-hydroxylase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
aklavinone + NADPH + H+ + O2 = epsilon-rhodomycinone + NADP+ + H2O
show the reaction diagram
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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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daunorubicin biosynthesis
SYSTEMATIC NAME
IUBMB Comments
aklavinone,NADPH:oxygen oxidoreductase (12-hydroxylating)
The enzymes from the Gram-positive bacteria Streptomyces peucetius and Streptomyces purpurascens participate in the biosynthesis of daunorubicin, doxorubicin and rhodomycins. The enzyme from Streptomyces purpurascens is an FAD monooxygenase.
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
11-deoxy-beta-L-rhodomycinone + NADPH + H+ + O2
beta-rhodomycinone + NADP+ + H2O
show the reaction diagram
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11-deoxy-L-rhodomycinone is a better substrate than aklavinone
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?
aklavinone + NADH + H+ + O2
epsilon-rhodomycinone + NAD+ + H2O
show the reaction diagram
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the enzyme participates in the biosynthesis of daunorubicin, doxorubicin and rhodomycins
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?
aklavinone + NADPH + H+ + O2
epsilon-rhodomycinone + NADP+ + H2O
show the reaction diagram
additional information
?
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no activity with decarbomethoxyaklavinone or 15-demethoxyaklavinone
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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
aklavinone + NADPH + H+ + O2
epsilon-rhodomycinone + NADP+ + H2O
show the reaction diagram
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADH
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aklavinone-11-hydroxylase can use both NADH and NADPH as coenzyme but it is slowly inactivated in the presence of NADH
NADPH
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2,3-Butanedione
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Phenylglyoxal
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NADPH protects against inactivation of aklavinone-11-hydroxylase by phenylglyoxal
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.01
aklavinone
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pH and temperature not specified in the publication
2
NADPH
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pH and temperature not specified in the publication
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
4.8
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calculated from sequence
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
57436
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x * 57436, calculated from sequence
60000
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1 * 60000
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
monomer
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1 * 60000
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
crystal structure of a ternary complex of this enzyme from Streptomyces purpurascens, RdmE, with FAD and the substrate aklavinone
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in doxorubicin-sensitive Streptomyces galilaeus ATCC 31133. Transformation of Streptomyces galilaeus ATCC 31133 with plasmid pMC213 containing the aklavinone 11-hydroxylase gene (dnrF) results in the production of many red pigments. A new metabolite is purified, and the position of the newly introduced hydroxyl group is determined. The result indicates that the aklavinone 11-hydroxylase gene is stably expressed in Streptomyces galilaeus ATCC 31133 and that it gives rise to a hybrid aclacinomycin A which shows highly specific in vitro cytotoxicity against leukemia and melanoma cell lines
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heterologous expression of dnrF in Streptomyces liwidans TK23 and in Escherichia coli. Since the fusion protein does not show any hydroxylase activity, the dnrF gene is cloned into the pT7-7 vector that allows the expression of an unfused DnrF protein
overexpression of the gene in Streptomyces lividans
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
R373X
mutants at position Arg373 retain catalytic activity close to wild-type level
Y224F
inactive mutant enzyme