Information on EC 2.5.1.104 - N1-aminopropylagmatine synthase

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The expected taxonomic range for this enzyme is: Archaea, Bacteria

EC NUMBER
COMMENTARY hide
2.5.1.104
-
RECOMMENDED NAME
GeneOntology No.
N1-aminopropylagmatine synthase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
S-adenosyl 3-(methylthio)propylamine + agmatine = S-methyl-5'-thioadenosine + N1-(3-aminopropyl)agmatine
show the reaction diagram
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-
-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
spermidine biosynthesis III
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-
polyamine pathway
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SYSTEMATIC NAME
IUBMB Comments
S-adenosyl 3-(methylthio)propylamine:agmatine 3-aminopropyltransferase
The enzyme is involved in the biosynthesis of spermidine from agmatine in some archaea and bacteria. The enzyme from the Gram-negative bacterium Thermus thermophilus accepts agmatine, spermidine and norspermidine with similar catalytic efficiency. The enzymes from the archaea Pyrococcus furiosus and Thermococcus kodakarensis prefer agmatine, but can utilize cadaverine, putrescine and propane-1,3-diamine with much lower catalytic efficiency. cf. EC 2.5.1.16, spermidine synthase, and EC 2.5.1.23, sym-norspermidine synthase.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
SwissProt
Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
S-adenosyl 3-(methylthio)propylamine + agmatine
5'-S-methyl-5'-thioadenosine + N1-aminopropylagamatine
show the reaction diagram
the enzyme is involved in polyamine biosynthesis
-
-
?
S-adenosyl 3-(methylthio)propylamine + agmatine
5'-S-methyl-5'-thioadenosine + N1-aminopropylagmatine
show the reaction diagram
S-adenosyl 3-(methylthio)propylamine + agmatine
S-methyl-5'-thioadenosine + N1-aminopropylagmatine
show the reaction diagram
-
-
-
-
?
S-adenosyl 3-(methylthio)propylamine + cadaverine
5'-S-methyl-5'-thioadenosine + N-(3-aminopropyl)cadaverine
show the reaction diagram
S-adenosyl 3-(methylthio)propylamine + homospermidine
S-methyl-5'-thioadenosine + ?
show the reaction diagram
-
low activity
-
-
?
S-adenosyl 3-(methylthio)propylamine + N,N'-bis(3-aminopropyl)-1,3-propanediamine
S-methyl-5'-thioadenosine + ?
show the reaction diagram
-
i.e. thermine. Low activity
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-
?
S-adenosyl 3-(methylthio)propylamine + norspermidine
S-methyl-5'-thioadenosine + N,N'-bis(3-aminopropyl)-1,3-propanediamine
show the reaction diagram
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i.e. thermine
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?
S-adenosyl 3-(methylthio)propylamine + propane-1,3-diamine
5'-S-methyl-5'-thioadenosine + bis(3-aminopropyl)amine
show the reaction diagram
2.9% of the activity compared to cadaverine
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-
?
S-adenosyl 3-(methylthio)propylamine + putrescine
5'-S-methyl-5'-thioadenosine + spermidine
show the reaction diagram
S-adenosyl 3-(methylthio)propylamine + spermidine
5'-S-methyl-5'-thioadenosine + spermine
show the reaction diagram
0.8% of the activity compared to cadaverine
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-
?
S-adenosyl 3-(methylthio)propylamine + spermidine
S-methyl-5'-thioadenosine + spermine
show the reaction diagram
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no formation of thermospermine (i.e. 1,12-diamino-4,8-diazadodecane)
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?
S-adenosyl 3-(methylthio)propylamine + tris(3-aminopropyl)amine
S-methyl-5'-thioadenosine + N4-aminopropylthermine
show the reaction diagram
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i.e. mitsubishine. Low activity. No formation of tetrakis(3-aminopropyl)ammonium
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?
additional information
?
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only faint activities (less than 10% of spermidine) are detected for diaminopropane [NH2(CH2)3NH2], putrescine, spermine, and caldopentamine
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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
S-adenosyl 3-(methylthio)propylamine + agmatine
5'-S-methyl-5'-thioadenosine + N1-aminopropylagamatine
show the reaction diagram
Q5JFG9
the enzyme is involved in polyamine biosynthesis
-
-
?
S-adenosyl 3-(methylthio)propylamine + agmatine
5'-S-methyl-5'-thioadenosine + N1-aminopropylagmatine
show the reaction diagram
S-adenosyl 3-(methylthio)propylamine + cadaverine
5'-S-methyl-5'-thioadenosine + N-(3-aminopropyl)cadaverine
show the reaction diagram
Q8U4G1
agmatine is the physiological substrate in the constitutive synthesis of spermidine, while cadaverine acts as an aminopropyl acceptor under stress conditions when an active and rapid synthesis of N-(3-aminopropyl)cadaverine could be required
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-
?
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0076 - 0.77
agmatine
0.0807 - 3.77
cadaverine
0.57
norspermidine
-
pH 9.0, 37°C
1.88
propane-1,3-diamine
pH 7.4, 70°C
1.053 - 7.7
putrescine
1.64
S-adenosyl 3-(methylthio)propylamine
-
pH 9.0, 37°C
0.00173
spermidine
-
pH 9.0, 37°C
38.31
tris(3-aminopropyl)amine
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pH 9.0, 37°C
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.1 - 0.37
agmatine
0.02 - 2.09
cadaverine
0.53
norspermidine
Thermus thermophilus
-
pH 9.0, 37°C
0.06
propane-1,3-diamine
Pyrococcus furiosus
Q8U4G1
pH 7.4, 70°C
0.18 - 0.3
putrescine
0.73
S-adenosyl 3-(methylthio)propylamine
Thermus thermophilus
-
pH 9.0, 37°C
0.65
spermidine
Thermus thermophilus
-
pH 9.0, 37°C
0.29
tris(3-aminopropyl)amine
Thermus thermophilus
-
pH 9.0, 37°C
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
13.4 - 480
agmatine
505
0.29 - 0.55
cadaverine
533
920
norspermidine
Thermus thermophilus
-
pH 9.0, 37°C
7488
0.032
propane-1,3-diamine
Pyrococcus furiosus
Q8U4G1
pH 7.4, 70°C
2284
0.023 - 0.29
putrescine
155
450
S-adenosyl 3-(methylthio)propylamine
Thermus thermophilus
-
pH 9.0, 37°C
3298
375
spermidine
Thermus thermophilus
-
pH 9.0, 37°C
148
7.6
tris(3-aminopropyl)amine
Thermus thermophilus
-
pH 9.0, 37°C
42210
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
2.4
-
pH 8.5, 60°C
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
8.5
-
at 60°C
9.5
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at 37°C
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
70 - 103
70°C: about 50% of maximal activity, 103°C: about 50% of maximal activity
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
32334
2 * 32334, calculated from sequence
32500
-
x * 32500, SDS-PAGE
32600
2 * 32600, SDS-PAGE
36006
-
4 * 36006, calculated from sequence
65000
gel filtration
130000
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gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
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x * 32500, SDS-PAGE
homodimer
2 * 32334, calculated from sequence; 2 * 32600, SDS-PAGE
homotetramer
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4 * 36006, calculated from sequence
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
sitting drop vapor diffusion method, 1.8 A resolution
hanging-drop vapor diffusion method
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pH STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
10
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stable around pH 10.0 at room temperature
720250
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
108
transition temperature
112
transition temperature in presence of 5 mM cadaverine
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli