Ligand putrescine

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Basic Ligand Information

Molecular Structure
Picture of putrescine (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C4H12N2
putrescine
WQZGKKKJIJFFOK-FPRJBGLDSA-N
Synonyms:
1,4-butanediamine, 1,4-diaminobutane, butane-1,4-diamine, Diaminobutane, NH2(CH2)4NH2, putrescine[side 2], Tetramethylenediamine
Pathway Source
Pathways
BRENDA
polyamine pathway
KEGG
ABC transporters, Arginine and proline metabolism, Biosynthesis of alkaloids derived from ornithine, lysine and nicotinic acid, Biosynthesis of plant secondary metabolites, Biosynthesis of secondary metabolites more
MetaCyc
alcaligin biosynthesis, homospermidine biosynthesis I, homospermidine biosynthesis II, L-arginine degradation III (arginine decarboxylase/agmatinase pathway), L-arginine degradation IV (arginine decarboxylase/agmatine deiminase pathway) more


Show all pahtways known for Show all BRENDA pathways known for putrescine

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (52 results)

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EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
putrescine + O2 + H2O = 4-aminobutanal + NH3 + H2O2
show the reaction diagram
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putrescine + H2O + O2 = ?
show the reaction diagram
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L-aspartate 4-semialdehyde + putrescine + NADPH + H+ = carboxyspermidine + H2O + NADP+
show the reaction diagram
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S-adenosyl-L-methionine + putrescine = S-adenosyl-L-homocysteine + N-methylputrescine
show the reaction diagram
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caffeoyl-CoA + putrescine = CoA + N-caffeoylputrescine
show the reaction diagram
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acetyl-CoA + putrescine = CoA + acetylputrescine
show the reaction diagram
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putrescine + pyruvate = 4-aminobutanal + alanine
show the reaction diagram
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putrescine + 2-oxoglutarate = 4-aminobutanal + L-glutamate
show the reaction diagram
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putrescine + 2-oxoglutarate = 1-pyrroline + L-glutamate + H2O
show the reaction diagram

In Vivo Product in Enzyme-catalyzed Reactions (15 results)

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EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
N-carbamoylputrescine + H2O = putrescine + CO2 + NH3
show the reaction diagram
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acetylputrescine + H2O = acetate + putrescine
show the reaction diagram
-
-
agmatine + H2O = putrescine + urea
show the reaction diagram
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-
D-ornithine = putrescine + CO2
show the reaction diagram
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-
L-ornithine = putrescine + CO2
show the reaction diagram
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-
L-ornithine = putrescine + CO2
show the reaction diagram
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-
ATP + H2O + putrescine-[polyamine-binding protein][side 1] = ADP + phosphate + putrescine[side 2] + [polyamine-binding protein][side 1]
show the reaction diagram
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-

Substrate in Enzyme-catalyzed Reactions (198 results)

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EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
putrescine + O2 + H2O = 4-aminobutanal + NH3 + H2O2
show the reaction diagram
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putrescine + O2 + H2O = ?
show the reaction diagram
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putrescine + H2O + 2,6-dichlorophenol indophenol = 4-aminobutanal + NH3 + reduced 2,6-dichlorophenol indophenol
show the reaction diagram
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L-aspartate 4-semialdehyde + putrescine + NADPH + H+ = carboxyspermidine + H2O + NADP+
show the reaction diagram
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carbamoyl phosphate + diaminobutane = phosphate + ?
show the reaction diagram
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2 sinapoyl-CoA + putrescine = ?
show the reaction diagram
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S-adenosyl 3-(methylthio)propylamine + putrescine = 5'-S-methyl-5'-thioadenosine + spermidine
show the reaction diagram
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S-adenosylmethioninamine + putrescine = 5'-S-methyl-5'-thioadenosine + spermidine
show the reaction diagram
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putrescine + pyruvate = 4-aminobutanal + alanine
show the reaction diagram
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1,4-diaminobutane + pyruvate = ? + L-alanine
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (61 results)

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EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
carboxyspermidine + NADP+ + H2O = L-aspartic 4-semialdehyde + putrescine + NADPH + H+
show the reaction diagram
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carboxyspermidine + H2O + NADP+ = L-aspartate 4-semialdehyde + putrescine + NADPH + H+
show the reaction diagram
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[eIF5A-precursor]-lysine + homospermidine = [eIF5A-precursor]-deoxyhypusine + putrescine
show the reaction diagram
acetylputrescine + H2O = acetate + putrescine
show the reaction diagram
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acetylputrescine + H2O = acetate + putrescine
show the reaction diagram
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agmatine + H2O = 1,4-diaminobutane + urea
show the reaction diagram
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agmatine + H2O = putrescine + urea
show the reaction diagram
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agmatine + H2O = putrescine + urea
show the reaction diagram
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agmatine + H2O = putrescine + urea
show the reaction diagram
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D-ornithine = putrescine + CO2
show the reaction diagram
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L-ornithine = 1,4-diaminobutane + CO2
show the reaction diagram
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L-ornithine = putrescine + CO2
show the reaction diagram
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L-gamma-glutamylputrescine = putrescine + 5-oxo-L-proline
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (307 results)

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EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
11% activation at 5 mM
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up to 50% stimulation at 1 mm
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activates, inhibitory at optimal Mg2+ concentration
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stimulates
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slight stimulation
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aliphatic, positively charged polyamine, required for in vitro activity of ORF47, polyamine depletion leads to 80% reduced activity
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optimal polymerization activity requires polyamines, 2fold increase in activity at 30 mM
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can replace missing Mg2+ to a small extent
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divalent cation, metal or polyamine is required, 0.01 M putrescine is as effective as Mg2+
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activate in presence of Mg2+, no activation in absence of Mg2+. Effective at 2-5 mM
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PLC d1
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activity is increased 6fold at 10 mM
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maximal stimulation at 6 mM
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but it inhibits at concentrations about 14 mM agmatine
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treatment of peach shoots from Mochizuki with exogenous putrescine (indirect product of ADC) remarkably induces accumulation of ADC mRNA, incubation of shoots in 1 and 5 mM exogenous putrescine for 2 days leads to obvious and significant increase in endogenous putrescine
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enhances activity against poly(C) and yeast RNA
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can partially replace Mg2+ in activation, with 32% efficiency
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optimal concentration: 5.5 mM
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Inhibitor in Enzyme-catalyzed Reactions (113 results)

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EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
i.e. 1,4-diaminobutane
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85% of initial activity at 0.5 mM
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12 mM
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the early decrease of glutathione reductase activity in leaves treated with polyamines can be due to a direct interaction of these compounds with the enzyme
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inhibition at optimal Mg2+-concentration
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1 mM, 42% inhibition
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10 mM, 74% inhibition in the presence of 0.5 mM N-acetyl-L-glutamate
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above 30 mM
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1 mM, less than 50% inhibition
15-25% inhibition with 5 mM; 15-25% inhibition with 5 mM; 15-25% inhibition with 5 mM
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putrescine is less efficient than divalent cations in reducing isoform PLCbeta1 activity
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putrescine, glycogen debranching enzyme, slight inhibition
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inhibition above 6 mM
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weak
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putrescine uptake by the enzyme is gradually inhibited by increasing levels of putrescine
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3D Structure of Enzyme-Ligand-Complex (PDB) (273 results)

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EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (66 results)

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EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.025
-
pH 8.5, 37°C
0.3
-
pH 7.3, 30°C, recombinant His6-tagged enzyme
0.0032
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+ spermidine
5.94
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pH 8.0 37°C, recombinant enzyme

KM Value (164 results)

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EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0225
-
-
43.5
-
pH 8.5, 37°C
0.2369
-
pH 7.3, 30°C, recombinant His6-tagged enzyme
3.85
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pH 7.5, 78°C
0.0769
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pH 10.0, temperature not specified in the publication
2.5
-
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44.6
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pH 8.0 37°C, recombinant enzyme

Ki Value (15 results)

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EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
19.1
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at pH 8.0 and 55°C
0.13
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pH 6.0, 25°C
0.0017
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-
1.45
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References & Links

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