1.5.3.13: N1-acetylpolyamine oxidase
This is an abbreviated version!
For detailed information about N1-acetylpolyamine oxidase, go to the full flat file.
Word Map on EC 1.5.3.13
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1.5.3.13
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spermine
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putrescine
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diamine
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ornithine
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oxidases
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n1-acetyltransferase
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s-adenosylmethionine
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n1-acetylspermine
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fad-dependent
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monoamine
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3-aminopropanal
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1,3-diaminopropane
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cadaverine
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apoplastic
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aminoaldehydes
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aminoguanidine
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acrolein
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back-conversion
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alpha-difluoromethylornithine
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samdc
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n1-acetylated
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thermospermine
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norspermidine
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n8-acetylspermidine
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tetraamine
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1.4.3.6
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analysis
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medicine
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pharmacology
- 1.5.3.13
- spermine
- putrescine
-
diamine
- ornithine
- oxidases
-
n1-acetyltransferase
- s-adenosylmethionine
- n1-acetylspermine
-
fad-dependent
-
monoamine
- 3-aminopropanal
- 1,3-diaminopropane
- cadaverine
- apoplastic
- aminoaldehydes
- aminoguanidine
- acrolein
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back-conversion
- alpha-difluoromethylornithine
- samdc
-
n1-acetylated
- thermospermine
- norspermidine
- n8-acetylspermidine
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tetraamine
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1.4.3.6
- analysis
- medicine
- pharmacology
Reaction
Synonyms
APAO, AtPAO5, Bjpao2, EC 1.5.3.11, HPAO, hPAO-1, More, MPAO, N1-acetyl polyamine oxidase, N1-acetylpolyamine oxidase, PAO, PAO5, PAOh1, PAOX, polyamine oxidase, SelPAO5
ECTree
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Substrates Products
Substrates Products on EC 1.5.3.13 - N1-acetylpolyamine oxidase
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REACTION DIAGRAM
(R)-alpha-methylspermidine + O2 + H2O
?
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PAO supplemented with benzaldehyde predominantly catalyzes the cleavage of (R)-isomer of alpha-methylspermidine, whereas in the presence of pyridoxal the (S)-alpha-methylspermidine is preferred
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-
?
(S)-alpha-methylspermidine + O2 + H2O
?
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PAO supplemented with benzaldehyde predominantly catalyzes the cleavage of (R)-isomer of alpha-methylspermidine, whereas in the presence of pyridoxal the (S)-alpha-methylspermidine is preferred
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-
?
(S)-N1-(2-methyl-1-butyl)-N11-ethyl-4,8-diazaundecane-1,11-diamine + O2 + H2O
?
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-
-
?
alpha-methylspermidine + O2 + H2O
?
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weak oxidation in presence of benzaldehyde, no oxidation without benzaldehyde
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-
?
alpha-methylspermine + O2 + H2O
?
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oxidation in presence of benzaldehyde, no oxidation without benzaldehyde
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-
?
alpha-methylspermine + O2 + H2O
spermidine + alpha-methylspermidine + ?
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-
-
-
?
N,N'-bis-(3-benzylaminopropyl)butane-1,4-diamine + O2 + H2O
N1-(3-benzylaminopropyl)butane-1,4-diamine + H2O2 + ?
-
-
main product
-
?
N,N'-bis-(3-benzylaminopropyl)butane-1,4-diamine + O2 + H2O
N1-(3-benzylaminopropyl)butane-1,4-diamine + N-(3-aminopropyl)-N'-(3-Benzylaminopropyl)butane-1,4-diamine + H2O2
-
-
-
-
?
N,N'-bis-(3-ethylaminopropyl)butane-1,4-diamine + O2 + H2O
N1-(3-ethylaminopropyl)butane-1,4-diamine + H2O2 + ?
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minor N4-endo cleavage pathways resulting in formation of N1-ethylpropane-1,3-diamine
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-
?
N-(3-benzylaminopropyl)-N'-(3-ethylaminopropyl)butane-1,4-diamine + O2 + H2O
N1-(3-ethylaminopropyl)butane-1,4-diamine + H2O2 + ?
-
-
-
-
?
N-[(2R)-4-[(4-aminobutyl)amino]butan-2-yl]pyridine-4-carboxamide + O2 + H2O
putrescine + (3R)-3-[(pyridin-4-yl)amino]butanal + H2O2
-
-
-
?
N-[(2S)-4-[(4-aminobutyl)amino]butan-2-yl]pyridine-4-carboxamide + O2 + H2O
putrescine + (3S)-3-[(pyridin-4-yl)amino]butanal + H2O2
-
-
-
?
N1,N11-didansylnorspermine + O2 + H2O
1-dansylnorspermidine + 1-dansylamido-3-propanal + H2O2
N1-(3-benzylaminopropyl)butane-1,4-diamine + O2 + H2O
spermidine + H2O2 + benzylalcohol
-
-
-
-
?
N1-(3-[[(thiophen-2-yl)methyl]amino]propyl)octane-1,8-diamine + O2 + H2O
octane-1,8-diamine + N1-[(thiophen-2-yl)methyl]propanal + H2O2
-
-
-
?
N1-acetyl-2-methylspermidine + O2 + H2O
putrescine + N-(2-methyl-3-oxopropyl)acetamide + H2O2
-
-
-
?
N1-acetyl-8-methylspermidine + O2 + H2O
pentane-1,4-diamine + 3-acetamidopropanal + H2O2
-
-
-
?
N1-acetylspermidine + O2 + H2O
putrescine + 3-acetaminopropanal + H2O2
-
-
-
?
N1-acetylspermine + O2 + H2O
spermidine + 3-acetaminopropanal + H2O2
-
-
-
?
N1-benzoyl-(R)-alpha-methylspermidine + O2 + H2O
putrescine + N-[(2R)-4-oxobutan-2-yl]benzamide + H2O2
-
-
-
?
N1-benzoyl-(S)-alpha-methylspermidine + O2 + H2O
putrescine + N-[(2S)-4-oxobutan-2-yl]benzamide + H2O2
-
-
-
?
N1-benzyl-propane-1,3-diamine + O2 + H2O
propane-1,3-diamine + H2O2 + benzylalcohol
-
-
-
-
?
N1-benzyldodecane-1,12-diamine + O2 + H2O
dodecane-1,12-diamine + N1-benzylpropanal + H2O2
-
-
-
?
N1-benzylspermine + O2 + H2O
spermidine + 3-(benzylamino)propanal + H2O2
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-
-
?
N1-ethyl-N11-(cycloheptyl)methyl-4,8-diazaundecane-1,11-diamine + O2 + H2O
?
-
-
-
?
N1-phenyl-(R)-alpha-methylspermidine + O2 + H2O
putrescine + (3R)-3-anilinobutanal + H2O2
-
-
-
?
N1-phenyl-(S)-alpha-methylspermidine + O2 + H2O
putrescine + (3S)-3-anilinobutanal + H2O2
-
-
-
?
N1-[(naphthalen-2-yl)methyl]spermine + O2 + H2O
spermidine + N1-[(naphthalen-2-yl)methyl]propanal + H2O2
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-
-
?
N1-[(pyridin-2-yl)methyl]spermine + O2 + H2O
spermidine + N1-[(pyridin-2-yl)methyl]propanal + H2O2
-
-
-
?
N1-[(thiophen-2-yl)methyl]spermine + O2 + H2O
spermidine + N1-[(thiophen-2-yl)methyl]propanal + H2O2
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-
-
?
1-dansylnorspermidine + 1-dansylamido-3-propanal + H2O2
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-
-
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?
N1,N11-didansylnorspermine + O2 + H2O
1-dansylnorspermidine + 1-dansylamido-3-propanal + H2O2
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-
-
-
?
N1-acetylspermidine + 3-acetamidopropanal + H2O2
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-
-
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?
N1,N12-diacetylspermine + O2 + H2O
N1-acetylspermidine + 3-acetamidopropanal + H2O2
N1-acetylspermine is first liberated as a product and then oxidized further to putrescine
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-
?
putrescine + 3-acetamidopropanal + H2O2
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?
N1-acetylspermidine + O2 + H2O
putrescine + 3-acetamidopropanal + H2O2
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-
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?
N1-acetylspermidine + O2 + H2O
putrescine + 3-acetamidopropanal + H2O2
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the enzyme is involved in polyamine catabolism. The enzyme is a constitutively expressed enzyme that catalyzes the oxidative cleavage of N1-acetylpolyamines to yield a less basic polyamine, 3-acetylamidopropanal, and hydrogen peroxide
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-
?
N1-acetylspermidine + O2 + H2O
putrescine + 3-acetamidopropanal + H2O2
oxidized at the carbon on the exo-side of the N4-nitrogen
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-
?
spermidine + 3-acetamidopropanal + H2O2
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-
-
?
N1-acetylspermine + O2 + H2O
spermidine + 3-acetamidopropanal + H2O2
at pH 6.5, substrate preference is in the following decreasing order: thermospermine, N1-acetylspermine, norspermine, spermine, spermidine. Spermidine is catabolized at a very low rate. At pH 7.5, substrate preference is in the following decreasing order: spermine, norspermine, N1-acetylspermine, thermospermine, spermidine. Spermidine is catalyzed at a very low rate
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-
?
N1-acetylspermine + O2 + H2O
spermidine + 3-acetamidopropanal + H2O2
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-
-
?
N1-acetylspermine + O2 + H2O
spermidine + 3-acetamidopropanal + H2O2
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-
-
-
?
N1-acetylspermine + O2 + H2O
spermidine + 3-acetamidopropanal + H2O2
PAO preferentially oxidizes acetylspermine or acetylspermidine over spermine
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-
?
N1-acetylspermine + O2 + H2O
spermidine + 3-acetamidopropanal + H2O2
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-
-
?
N1-acetylspermine + O2 + H2O
spermidine + 3-acetamidopropanal + H2O2
oxidized at the carbon on the exo-side of the N4-nitrogen
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-
?
N1-acetylspermine + O2 + H2O
spermidine + 3-acetamidopropanal + H2O2
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-
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?
N1-acetylspermine + O2 + H2O
spermidine + 3-acetamidopropanal + H2O2
at pH 8.0, the substrate preference in decreasing order is as follows: spermine/thermospermine, N1-acetylspermine, norspermine, spermidine. At pH 7.0, the substrate preference in decreasing order is as follows: thermospermine, norspermine, spermine, N1-acetylspermine, spermidine
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?
?
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no activity in absence of aldehydes, weak activity in presence of aldehydes
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?
spermidine + O2 + H2O
?
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weak oxidation in presence of benzaldehyde, no oxidation without benzaldehyde
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-
?
spermine + O2 + H2O
?
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oxidation in presence of benzaldehyde, no oxidation without benzaldehyde
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-
?
spermine + O2 + H2O
?
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rather poor substrate for hPAO, aldehyde supplementation greatly increased its degradation
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-
?
spermidine + 3-aminopropanal + H2O2
least favoured substrate
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-
?
?
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Bjpao2 shows no activity with spermine
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?
additional information
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PAO expression is inducible by polyamine analogues and thus may contribute to the inhibition of cell growth
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?
additional information
?
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PAO expression is inducible by polyamine analogues and thus may contribute to the inhibition of cell growth
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?
additional information
?
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no efficient hydrolysis of: spermine, spermidine and N8-acetylspermidine, SL-11144, SL-11150, SL-11158 and SL-11156
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-
?
additional information
?
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no efficient hydrolysis of: spermine, spermidine and N8-acetylspermidine, SL-11144, SL-11150, SL-11158 and SL-11156
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-
?
additional information
?
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no production of spermidine from bis-alpha-methylspermine, hPAO
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-
?
additional information
?
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APAO is capable of metabolizing several N-alkylated polyamine derivatives, substrate specificity, overview. N1-(3-Ethylaminopropyl)butane-1,4-diamine trihydrochloride is a poor substrate
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-
?
additional information
?
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assay method development and validation, evaluation of quantitative determination of reaction products, overview
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?
additional information
?
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no substrate: N1-acetyl-3-methylspermidine
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additional information
?
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PAOX naturally metabolizes achiral N1-acetylated polyamines, displays aldehyde-controllable stereospecificity with chiral 1-methylated polyamines, like (R)- and (S)-1-methylspermidine
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additional information
?
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PAOX naturally metabolizes achiral N1-acetylated polyamines, displays aldehyde-controllable stereospecificity with chiral 1-methylated polyamines, like (R)- and (S)-1-methylspermidine
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