1.14.13.195: L-ornithine N5-monooxygenase (NADPH)
This is an abbreviated version!
For detailed information about L-ornithine N5-monooxygenase (NADPH), go to the full flat file.
Word Map on EC 1.14.13.195
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1.14.13.195
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flavin
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fumigatus
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aspergillus
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flavin-dependent
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pyoverdine
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nadp+
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c4a-hydroperoxyflavin
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hydroxamate
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hydroxamate-containing
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flavin-containing
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non-ribosomal
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half-reaction
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n-hydroxylating
- 1.14.13.195
- flavin
- fumigatus
- aspergillus
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flavin-dependent
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pyoverdine
- nadp+
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c4a-hydroperoxyflavin
- hydroxamate
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hydroxamate-containing
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flavin-containing
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non-ribosomal
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half-reaction
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n-hydroxylating
Reaction
Synonyms
Af-OMO, CchB, flavin-dependent monooxygenase, L-Orn N5-oxygenase, L-ornithine N5-hydroxylase, L-ornithine-Ndelta-oxygenase, monooxygenase EtcB, omega-amino acid monooxygenase, ornithine hydroxylase, ornithine N5-monooxygenase, PsbA, PvdA, SidA, siderophore A
ECTree
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Substrates Products
Substrates Products on EC 1.14.13.195 - L-ornithine N5-monooxygenase (NADPH)
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REACTION DIAGRAM
L-ornithine + NADH + H+ + O2
N5-hydroxy-L-ornithine + NAD+ + H2O
Q5SE95
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-
-
?
N6-hydroxy-L-lysine + NADP+ + H2O
substrate with lower efficiency compared to L-ornithine
-
-
?
L-lysine + NADPH + H+ + O2
N6-hydroxy-L-lysine + NADP+ + H2O
substrate with lower efficiency compared to L-ornithine
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-
?
N5-hydroxy-L-ornithine + NADP+ + H2O
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-
-
-
?
L-ornithine + NADPH + H+ + O2
N5-hydroxy-L-ornithine + NADP+ + H2O
Q5SE95
-
-
-
?
L-ornithine + NADPH + H+ + O2
N5-hydroxy-L-ornithine + NADP+ + H2O
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-
-
-
?
L-ornithine + NADPH + H+ + O2
N5-hydroxy-L-ornithine + NADP+ + H2O
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-
-
?
L-ornithine + NADPH + H+ + O2
N5-hydroxy-L-ornithine + NADP+ + H2O
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-
-
-
?
L-ornithine + NADPH + H+ + O2
N5-hydroxy-L-ornithine + NADP+ + H2O
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-
-
?
L-ornithine + NADPH + H+ + O2
N5-hydroxy-L-ornithine + NADP+ + H2O
-
-
-
-
?
L-ornithine + NADPH + H+ + O2
N5-hydroxy-L-ornithine + NADP+ + H2O
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first step in pyoverdine biosynthesis
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-
?
L-ornithine + NADPH + H+ + O2
N5-hydroxy-L-ornithine + NADP+ + H2O
-
-
-
-
?
L-ornithine + NADPH + H+ + O2
N5-hydroxy-L-ornithine + NADP+ + H2O
-
-
-
?
L-ornithine + NADPH + H+ + O2
N5-hydroxy-L-ornithine + NADP+ + H2O
-
-
-
-
?
L-ornithine + NADPH + H+ + O2
N5-hydroxy-L-ornithine + NADP+ + H2O
first step in pyoverdine biosynthesis
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-
?
L-ornithine + NADPH + H+ + O2
N5-hydroxy-L-ornithine + NADP+ + H2O
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hydroxylation of the primary amine of ornithine in the initial step of the biosynthesis of siderophore pyoverdin
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-
?
L-ornithine + NADPH + H+ + O2
N5-hydroxy-L-ornithine + NADP+ + H2O
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hydroxylation of the primary amine of ornithine
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-
?
L-ornithine + NADPH + H+ + O2
N5-hydroxy-L-ornithine + NADP+ + H2O
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no activity with D-ornithine
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-
?
L-ornithine + NADPH + H+ + O2
N5-hydroxy-L-ornithine + NADP+ + H2O
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PvdA is highly specific for both substrate and coenzyme, PvdA/FAD forms a ternary complex with NADPH and ornithine for catalysis
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-
?
L-ornithine + NADPH + H+ + O2
N5-hydroxy-L-ornithine + NADP+ + H2O
-
one of the initial enzymes in the biosynthetic pathway of pyoverdine I the major siderophore produced by Pseudomonas aeruginosa PAO1 to import iron
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-
?
L-ornithine + NADPH + H+ + O2
N5-hydroxy-L-ornithine + NADP+ + H2O
-
-
-
-
?
L-ornithine + NADPH + H+ + O2
N5-hydroxy-L-ornithine + NADP+ + H2O
-
first step in pyoverdine biosynthesis
-
-
?
L-ornithine + NADPH + H+ + O2
N5-hydroxy-L-ornithine + NADP+ + H2O
-
-
-
-
?
L-ornithine + NADPH + H+ + O2
N5-hydroxy-L-ornithine + NADP+ + H2O
-
first step in pyoverdine biosynthesis
-
-
?
L-ornithine + NADPH + H+ + O2
N5-hydroxy-L-ornithine + NADP+ + H2O
-
-
-
?
L-ornithine + NADPH + H+ + O2
N5-hydroxy-L-ornithine + NADP+ + H2O
the enzyme contains the FATGY signature in the putative substrate binding pocket
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-
?
L-ornithine + NADPH + H+ + O2
N5-hydroxy-L-ornithine + NADP+ + H2O
-
-
-
?
L-ornithine + NADPH + H+ + O2
N5-hydroxy-L-ornithine + NADP+ + H2O
the enzyme contains the FATGY signature in the putative substrate binding pocket
-
-
?
L-ornithine + NADPH + H+ + O2
N5-hydroxy-L-ornithine + NADP+ + H2O
-
-
-
-
?
L-ornithine + NADPH + H+ + O2
N5-hydroxy-L-ornithine + NADP+ + H2O
-
first step in pyoverdine biosynthesis
-
-
?
L-ornithine + NADPH + H+ + O2
N5-hydroxy-L-ornithine + NADP+ + H2O
-
-
-
-
?
L-ornithine + NADPH + H+ + O2
N5-hydroxy-L-ornithine + NADP+ + H2O
-
first step in pyoverdine biosynthesis
-
-
?
L-ornithine + NADPH + H+ + O2
N5-hydroxy-L-ornithine + NADP+ + H2O
-
-
-
-
?
L-ornithine + NADPH + H+ + O2
N5-hydroxy-L-ornithine + NADP+ + H2O
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the enzyme is involved in biosynthesis of N5-acetyl-N5-hydroxy-L-ornithine, a building block of the hydroxamate-type siderophore erythrochelin
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-
?
L-ornithine + NADPH + H+ + O2
N5-hydroxy-L-ornithine + NADP+ + H2O
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-
-
-
?
L-ornithine + NADPH + H+ + O2
N5-hydroxy-L-ornithine + NADP+ + H2O
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absolutely specific for L-ornithine
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-
?
L-ornithine + NADPH + H+ + O2
N5-hydroxy-L-ornithine + NADP+ + H2O
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-
-
-
?
L-ornithine + NADPH + H+ + O2
N5-hydroxy-L-ornithine + NADP+ + H2O
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absolutely specific for L-ornithine
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-
?
?
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Q5SE95
when the enzyme is reduced with NADPH and reacts with molecular oxygen, a C4a-hydroperoxyflavin intermediate is observed. When the enzyme is reduced with NADH, the intermediate is 2fold less stable. Steady-state kinetic isotope effect values for NADPH and NADH are 3 and 2 , respectively, due to differences in the rate of flavin reduction by these coenzymes. NADP+, and not NAD+, protects the enzyme from proteolysis, suggesting that it induces conformational changes upon binding
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?
additional information
?
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when the enzyme is reduced with NADPH and reacts with molecular oxygen, a C4a-hydroperoxyflavin intermediate is observed. When the enzyme is reduced with NADH, the intermediate is 2fold less stable. Steady-state kinetic isotope effect values for NADPH and NADH are 3 and 2 , respectively, due to differences in the rate of flavin reduction by these coenzymes. NADP+, and not NAD+, protects the enzyme from proteolysis, suggesting that it induces conformational changes upon binding
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?
additional information
?
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PvdA is the ornithine hydroxylase, which performs the first enzymatic step in preparation of hydroxamate siderophore derivatives, pyoverdin is the hydroxamate siderophore produced by the opportunistic pathogen Pseudomonas aeruginosa under the iron-limiting conditions of the human host, overview. Poor activity with DL-2,3-diaminopropionic acid and D-ornithine, no activity with L-norleucine, 5-aminopentanoic acid, DL-2,4-diaminobutyric acid, and 1,4-diaminobutane, and no activity with NADH as cofactor, substrate specificity, overview
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?
additional information
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extending the side chain by one methylene group to L-lysine results in significant NADPH oxidation without formation of the hydroxylated product, indicating that the reaction is uncoupled
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?
additional information
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H2O2 formation by NADPH oxidation in the absence of substrate in presence of FAD
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?
additional information
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the NADPH oxidase activity of the enzyme is tightly coupled to hydroxylamine formation
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?
additional information
?
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no activity with D-ornithine, N5-formylornithine, L-lysine, L-glutamate, L-glutamine, L-valine, and the tetrapeptide D-Orn-D-Thr-L-Orn-D-Orn, the enzyme performs NADPH oxidation with formation of H2O2, substrate specificity, overview
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?
additional information
?
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no activity with D-ornithine, N5-formylornithine, L-lysine, L-glutamate, L-glutamine, L-valine, and the tetrapeptide D-Orn-D-Thr-L-Orn-D-Orn, the enzyme performs NADPH oxidation with formation of H2O2, substrate specificity, overview
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?