BRENDA - Enzyme Database
show all sequences of 3.5.1.48

Synthesis and evaluation of N8-acetylspermidine analogues as inhibitors of bacterial acetylpolyamine amidohydrolase

Decroos, C.; Bowman, C.M.; Christianson, D.W.; Bioorg. Med. Chem. 21, 4530-4540 (2013)

Data extracted from this reference:

Cloned(Commentary)
Cloned (Commentary)
Organism
recombinant expression in Escherichia coli strain BL21(DE3)
Mycoplana ramosa
Engineering
Protein Variants
Commentary
Organism
H159A
catalytically inactive mutant
Mycoplana ramosa
Inhibitors
Inhibitors
Commentary
Organism
Structure
5-[(3-aminopropyl)amino]pentane-1-thiol
-
Mycoplana ramosa
5-[(3-aminopropyl)amino]pentylboronic acid
-
Mycoplana ramosa
6-[(3-aminopropyl)amino]-N-hydroxyhexanamide
-
Mycoplana ramosa
6-[(3-aminopropyl)amino]hexanoic acid
-
Mycoplana ramosa
7-[(3-aminopropyl)amino]-1,1,1-trifluoroheptan-2-one
-
Mycoplana ramosa
7-[(3-aminopropyl)amino]-1-methoxyheptan-2-one
-
Mycoplana ramosa
7-[(3-aminopropyl)amino]heptan-2-one
-
Mycoplana ramosa
additional information
design, synthesis, and evaluation of N8-acetylspermidine analogues bearing different zinc binding groups as potential inhibitors of the enzyme, overview. Most of the synthesized compounds exhibit modest potency, with IC50 values in the mid-micromolar range, but compounds bearing hydroxamate or trifluoromethylketone zinc binding groups exhibit enhanced inhibitory potency in the mid-nanomolar range. Three compounds exhibit very poor inhibitory potency against th enzyme, 6-[(3-aminopropyl)amino]hexanoic acid, S-{5-[(3-aminopropyl)amino]pentyl} thioacetate, and N1-[5-(methylsulfonyl)pentyl]propane-1,3-diamine dihydrochloride
Mycoplana ramosa
N',N''-bis(tert-butoxycarbonyl)-6-[(3-aminopropyl)amino]-N-hydroxyhexanamide
-
Mycoplana ramosa
N',N''-bis(tert-butoxycarbonyl)-6-[(3-aminopropyl)amino]-N-methoxy-N-methylhexanamide
-
Mycoplana ramosa
N,N'-bis(tert-butoxycarbonyl)-5-[(3-aminopropyl)amino]pentan-1-ol
-
Mycoplana ramosa
N,N'-bis(tert-butoxycarbonyl)-5-[(3-aminopropyl)amino]pentane-1-thiol
-
Mycoplana ramosa
N,N'-bis(tert-butoxycarbonyl)-6-[(3-aminopropyl)amino]hexanal
-
Mycoplana ramosa
N,N'-bis(tert-butoxycarbonyl)-6-[(3-aminopropyl)amino]hexanoic acid
-
Mycoplana ramosa
N,N'-bis(tert-butoxycarbonyl)-7-[(3-aminopropyl)amino]-1,1,1-trifluoroheptan-2-ol
-
Mycoplana ramosa
N,N'-bis(tert-butoxycarbonyl)-7-[(3-aminopropyl)amino]-1,1,1-trifluoroheptan-2-one
-
Mycoplana ramosa
N,N'-bis(tert-butoxycarbonyl)-7-[(3-aminopropyl)amino]-1-bromoheptan-2-ol
-
Mycoplana ramosa
N,N'-bis(tert-butoxycarbonyl)-7-[(3-aminopropyl)amino]-1-bromoheptan-2-one
-
Mycoplana ramosa
N,N'-bis(tert-butoxycarbonyl)-7-[(3-aminopropyl)amino]-1-methoxyheptan-2-ol
-
Mycoplana ramosa
N,N'-bis(tert-butoxycarbonyl)-7-[(3-aminopropyl)amino]-1-methoxyheptan-2-one
-
Mycoplana ramosa
N,N'-bis(tert-butoxycarbonyl)-7-[(3-aminopropyl)amino]heptan-2-one
-
Mycoplana ramosa
N1,N3-bis(tert-butoxycarbonyl)-N1-(5-bromopentyl)propane-1,3-diamine
-
Mycoplana ramosa
N1,N3-bis(tert-butoxycarbonyl)-N1-(hept-6-enyl)propane-1,3-diamine
-
Mycoplana ramosa
N1,N3-bis(tert-butoxycarbonyl)-N1-(pent-4-enyl)propane-1,3-diamine
-
Mycoplana ramosa
N1,N3-bis(tert-butoxycarbonyl)-N1-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pentyl]propane-1,3-diamine
-
Mycoplana ramosa
N1,N3-bis(tert-butoxycarbonyl)-N1-[5-(methylsulfonyl)pentyl]propane-1,3-diamine
-
Mycoplana ramosa
N1,N3-bis(tert-butoxycarbonyl)-N1-[5-(methylthio)pentyl]propane-1,3-diamine
-
Mycoplana ramosa
N1,N3-bis(tert-butoxycarbonyl)-N1-[5-(oxiran-2-yl)pentyl]propane-1,3-diamine
-
Mycoplana ramosa
N1-(hept-6-enyl)propane-1,3-diamine
-
Mycoplana ramosa
N1-(pent-4-enyl)propane-1,3-diamine
-
Mycoplana ramosa
N1-[5-(methylsulfonyl)pentyl]propane-1,3-diamine
-
Mycoplana ramosa
S-{5-[(3-aminopropyl)amino]pentyl} thioacetate
-
Mycoplana ramosa
S-{7-[(3-aminopropyl)amino]-2-oxoheptyl} ethanethioate
-
Mycoplana ramosa
S-{N,N'-bis(tert-butoxycarbonyl)-5-[(3-aminopropyl)amino]pentyl} thioacetate
-
Mycoplana ramosa
S-{N,N'-bis(tert-butoxycarbonyl)-7-[(3-aminopropyl)amino]-2-oxoheptyl}thioacetate
-
Mycoplana ramosa
Metals/Ions
Metals/Ions
Commentary
Organism
Structure
Zn2+
dependent on
Mycoplana ramosa
Natural Substrates/ Products (Substrates)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
ID
additional information
Mycoplana ramosa
the bacterial enzyme from Mycoplana ramosa has broader substrate specificity in comparison with mammalian enzyme. Its substrates include both small and large acetylpolyamines such as acetylputrescine, acetylcadaverine, N1- and N8-acetylspermidine, and N1-acetylspermine
?
-
-
?
N1-acetylspermidine + H2O
Mycoplana ramosa
-
acetate + spermidine
-
-
?
Organism
Organism
UniProt
Commentary
Textmining
Mycoplana ramosa
-
-
-
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
Substrate Product ID
acetylcadaverine + H2O
-
733494
Mycoplana ramosa
acetate + cadaverine
-
-
-
?
acetylputrescine + H2O
-
733494
Mycoplana ramosa
acetate + putrescine
-
-
-
?
additional information
the bacterial enzyme from Mycoplana ramosa has broader substrate specificity in comparison with mammalian enzyme. Its substrates include both small and large acetylpolyamines such as acetylputrescine, acetylcadaverine, N1- and N8-acetylspermidine, and N1-acetylspermine
733494
Mycoplana ramosa
?
-
-
-
?
additional information
usage of the commercially available Fluor-de-Lys deacetylase fluorogenic substrate fir enzyme activity assays
733494
Mycoplana ramosa
?
-
-
-
?
N1-acetylspermidine + H2O
-
733494
Mycoplana ramosa
acetate + spermidine
-
-
-
?
N1-acetylspermine + H2O
-
733494
Mycoplana ramosa
acetate + spermine
-
-
-
?
N8-acetylspermidine + H2O
-
733494
Mycoplana ramosa
acetate + spermidine
-
-
-
?
Subunits
Subunits
Commentary
Organism
dimer
-
Mycoplana ramosa
Synonyms
Synonyms
Commentary
Organism
acetylpolyamine amidohydrolase
-
Mycoplana ramosa
APAH
-
Mycoplana ramosa
N1-acetylspermidine deacetylase
-
Mycoplana ramosa
N8-acetylspermidine deacetylase
-
Mycoplana ramosa
Temperature Optimum [°C]
Temperature Optimum [°C]
Temperature Optimum Maximum [°C]
Commentary
Organism
25
-
assay at
Mycoplana ramosa
pH Optimum
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
8.2
-
assay at
Mycoplana ramosa
Cloned(Commentary) (protein specific)
Commentary
Organism
recombinant expression in Escherichia coli strain BL21(DE3)
Mycoplana ramosa
Engineering (protein specific)
Protein Variants
Commentary
Organism
H159A
catalytically inactive mutant
Mycoplana ramosa
Inhibitors (protein specific)
Inhibitors
Commentary
Organism
Structure
5-[(3-aminopropyl)amino]pentane-1-thiol
-
Mycoplana ramosa
5-[(3-aminopropyl)amino]pentylboronic acid
-
Mycoplana ramosa
6-[(3-aminopropyl)amino]-N-hydroxyhexanamide
-
Mycoplana ramosa
6-[(3-aminopropyl)amino]hexanoic acid
-
Mycoplana ramosa
7-[(3-aminopropyl)amino]-1,1,1-trifluoroheptan-2-one
-
Mycoplana ramosa
7-[(3-aminopropyl)amino]-1-methoxyheptan-2-one
-
Mycoplana ramosa
7-[(3-aminopropyl)amino]heptan-2-one
-
Mycoplana ramosa
additional information
design, synthesis, and evaluation of N8-acetylspermidine analogues bearing different zinc binding groups as potential inhibitors of the enzyme, overview. Most of the synthesized compounds exhibit modest potency, with IC50 values in the mid-micromolar range, but compounds bearing hydroxamate or trifluoromethylketone zinc binding groups exhibit enhanced inhibitory potency in the mid-nanomolar range. Three compounds exhibit very poor inhibitory potency against th enzyme, 6-[(3-aminopropyl)amino]hexanoic acid, S-{5-[(3-aminopropyl)amino]pentyl} thioacetate, and N1-[5-(methylsulfonyl)pentyl]propane-1,3-diamine dihydrochloride
Mycoplana ramosa
N',N''-bis(tert-butoxycarbonyl)-6-[(3-aminopropyl)amino]-N-hydroxyhexanamide
-
Mycoplana ramosa
N',N''-bis(tert-butoxycarbonyl)-6-[(3-aminopropyl)amino]-N-methoxy-N-methylhexanamide
-
Mycoplana ramosa
N,N'-bis(tert-butoxycarbonyl)-5-[(3-aminopropyl)amino]pentan-1-ol
-
Mycoplana ramosa
N,N'-bis(tert-butoxycarbonyl)-5-[(3-aminopropyl)amino]pentane-1-thiol
-
Mycoplana ramosa
N,N'-bis(tert-butoxycarbonyl)-6-[(3-aminopropyl)amino]hexanal
-
Mycoplana ramosa
N,N'-bis(tert-butoxycarbonyl)-6-[(3-aminopropyl)amino]hexanoic acid
-
Mycoplana ramosa
N,N'-bis(tert-butoxycarbonyl)-7-[(3-aminopropyl)amino]-1,1,1-trifluoroheptan-2-ol
-
Mycoplana ramosa
N,N'-bis(tert-butoxycarbonyl)-7-[(3-aminopropyl)amino]-1,1,1-trifluoroheptan-2-one
-
Mycoplana ramosa
N,N'-bis(tert-butoxycarbonyl)-7-[(3-aminopropyl)amino]-1-bromoheptan-2-ol
-
Mycoplana ramosa
N,N'-bis(tert-butoxycarbonyl)-7-[(3-aminopropyl)amino]-1-bromoheptan-2-one
-
Mycoplana ramosa
N,N'-bis(tert-butoxycarbonyl)-7-[(3-aminopropyl)amino]-1-methoxyheptan-2-ol
-
Mycoplana ramosa
N,N'-bis(tert-butoxycarbonyl)-7-[(3-aminopropyl)amino]-1-methoxyheptan-2-one
-
Mycoplana ramosa
N,N'-bis(tert-butoxycarbonyl)-7-[(3-aminopropyl)amino]heptan-2-one
-
Mycoplana ramosa
N1,N3-bis(tert-butoxycarbonyl)-N1-(5-bromopentyl)propane-1,3-diamine
-
Mycoplana ramosa
N1,N3-bis(tert-butoxycarbonyl)-N1-(hept-6-enyl)propane-1,3-diamine
-
Mycoplana ramosa
N1,N3-bis(tert-butoxycarbonyl)-N1-(pent-4-enyl)propane-1,3-diamine
-
Mycoplana ramosa
N1,N3-bis(tert-butoxycarbonyl)-N1-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pentyl]propane-1,3-diamine
-
Mycoplana ramosa
N1,N3-bis(tert-butoxycarbonyl)-N1-[5-(methylsulfonyl)pentyl]propane-1,3-diamine
-
Mycoplana ramosa
N1,N3-bis(tert-butoxycarbonyl)-N1-[5-(methylthio)pentyl]propane-1,3-diamine
-
Mycoplana ramosa
N1,N3-bis(tert-butoxycarbonyl)-N1-[5-(oxiran-2-yl)pentyl]propane-1,3-diamine
-
Mycoplana ramosa
N1-(hept-6-enyl)propane-1,3-diamine
-
Mycoplana ramosa
N1-(pent-4-enyl)propane-1,3-diamine
-
Mycoplana ramosa
N1-[5-(methylsulfonyl)pentyl]propane-1,3-diamine
-
Mycoplana ramosa
S-{5-[(3-aminopropyl)amino]pentyl} thioacetate
-
Mycoplana ramosa
S-{7-[(3-aminopropyl)amino]-2-oxoheptyl} ethanethioate
-
Mycoplana ramosa
S-{N,N'-bis(tert-butoxycarbonyl)-5-[(3-aminopropyl)amino]pentyl} thioacetate
-
Mycoplana ramosa
S-{N,N'-bis(tert-butoxycarbonyl)-7-[(3-aminopropyl)amino]-2-oxoheptyl}thioacetate
-
Mycoplana ramosa
Metals/Ions (protein specific)
Metals/Ions
Commentary
Organism
Structure
Zn2+
dependent on
Mycoplana ramosa
Natural Substrates/ Products (Substrates) (protein specific)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
ID
additional information
Mycoplana ramosa
the bacterial enzyme from Mycoplana ramosa has broader substrate specificity in comparison with mammalian enzyme. Its substrates include both small and large acetylpolyamines such as acetylputrescine, acetylcadaverine, N1- and N8-acetylspermidine, and N1-acetylspermine
?
-
-
?
N1-acetylspermidine + H2O
Mycoplana ramosa
-
acetate + spermidine
-
-
?
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
ID
acetylcadaverine + H2O
-
733494
Mycoplana ramosa
acetate + cadaverine
-
-
-
?
acetylputrescine + H2O
-
733494
Mycoplana ramosa
acetate + putrescine
-
-
-
?
additional information
the bacterial enzyme from Mycoplana ramosa has broader substrate specificity in comparison with mammalian enzyme. Its substrates include both small and large acetylpolyamines such as acetylputrescine, acetylcadaverine, N1- and N8-acetylspermidine, and N1-acetylspermine
733494
Mycoplana ramosa
?
-
-
-
?
additional information
usage of the commercially available Fluor-de-Lys deacetylase fluorogenic substrate fir enzyme activity assays
733494
Mycoplana ramosa
?
-
-
-
?
N1-acetylspermidine + H2O
-
733494
Mycoplana ramosa
acetate + spermidine
-
-
-
?
N1-acetylspermine + H2O
-
733494
Mycoplana ramosa
acetate + spermine
-
-
-
?
N8-acetylspermidine + H2O
-
733494
Mycoplana ramosa
acetate + spermidine
-
-
-
?
Subunits (protein specific)
Subunits
Commentary
Organism
dimer
-
Mycoplana ramosa
Temperature Optimum [°C] (protein specific)
Temperature Optimum [°C]
Temperature Optimum Maximum [°C]
Commentary
Organism
25
-
assay at
Mycoplana ramosa
pH Optimum (protein specific)
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
8.2
-
assay at
Mycoplana ramosa
Other publictions for EC 3.5.1.48
No.
1st author
Pub Med
title
organims
journal
volume
pages
year
Activating Compound
Application
Cloned(Commentary)
Crystallization (Commentary)
Engineering
General Stability
Inhibitors
KM Value [mM]
Localization
Metals/Ions
Molecular Weight [Da]
Natural Substrates/ Products (Substrates)
Organic Solvent Stability
Organism
Oxidation Stability
Posttranslational Modification
Purification (Commentary)
Reaction
Renatured (Commentary)
Source Tissue
Specific Activity [micromol/min/mg]
Storage Stability
Substrates and Products (Substrate)
Subunits
Synonyms
Temperature Optimum [°C]
Temperature Range [°C]
Temperature Stability [°C]
Turnover Number [1/s]
pH Optimum
pH Range
pH Stability
Cofactor
Ki Value [mM]
pI Value
IC50 Value
Activating Compound (protein specific)
Application (protein specific)
Cloned(Commentary) (protein specific)
Cofactor (protein specific)
Crystallization (Commentary) (protein specific)
Engineering (protein specific)
General Stability (protein specific)
IC50 Value (protein specific)
Inhibitors (protein specific)
Ki Value [mM] (protein specific)
KM Value [mM] (protein specific)
Localization (protein specific)
Metals/Ions (protein specific)
Molecular Weight [Da] (protein specific)
Natural Substrates/ Products (Substrates) (protein specific)
Organic Solvent Stability (protein specific)
Oxidation Stability (protein specific)
Posttranslational Modification (protein specific)
Purification (Commentary) (protein specific)
Renatured (Commentary) (protein specific)
Source Tissue (protein specific)
Specific Activity [micromol/min/mg] (protein specific)
Storage Stability (protein specific)
Substrates and Products (Substrate) (protein specific)
Subunits (protein specific)
Temperature Optimum [°C] (protein specific)
Temperature Range [°C] (protein specific)
Temperature Stability [°C] (protein specific)
Turnover Number [1/s] (protein specific)
pH Optimum (protein specific)
pH Range (protein specific)
pH Stability (protein specific)
pI Value (protein specific)
Expression
General Information
General Information (protein specific)
Expression (protein specific)
KCat/KM [mM/s]
KCat/KM [mM/s] (protein specific)
752780
Shinsky
Polyamine deacetylase structu ...
Danio rerio, Homo sapiens
Biochemistry
57
3105-3114
2018
-
2
-
-
-
-
2
-
-
2
-
2
-
6
-
-
-
-
-
-
-
-
4
-
8
-
-
-
-
-
-
-
-
-
-
-
-
2
-
-
-
-
-
-
2
-
-
-
2
-
2
-
-
-
-
-
-
-
-
4
-
-
-
-
-
-
-
-
-
-
6
6
-
-
-
754843
Hai
Histone deacetylase 10 struct ...
Danio rerio, Homo sapiens
Nat. Commun.
8
15368
2017
-
-
2
1
5
-
2
37
-
2
-
2
-
8
-
-
2
-
-
-
-
-
27
-
6
2
-
-
37
2
-
-
-
2
-
-
-
-
2
-
1
5
-
-
2
2
37
-
2
-
2
-
-
-
2
-
-
-
-
27
-
2
-
-
37
2
-
-
-
-
2
2
-
35
35
733494
Decroos
Synthesis and evaluation of N8 ...
Mycoplana ramosa
Bioorg. Med. Chem.
21
4530-4540
2013
-
-
1
-
1
-
35
-
-
1
-
2
-
5
-
-
-
-
-
-
-
-
7
1
4
1
-
-
-
1
-
-
-
-
-
-
-
-
1
-
-
1
-
-
35
-
-
-
1
-
2
-
-
-
-
-
-
-
-
7
1
1
-
-
-
1
-
-
-
-
-
-
-
-
-
172047
Wang
Effect of N8-acetylspermidine ...
Mus musculus
Biochem. Pharmacol.
57
1095-1103
1999
-
-
-
-
-
-
2
-
1
-
-
-
-
1
-
-
-
-
-
1
-
-
2
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
2
-
-
1
-
-
-
-
-
-
-
-
1
-
-
2
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
172048
Menezes
Differentiation of PC 12 cells ...
Rattus sp.
Proc. West. Pharmacol. Soc.
36
21-24
1993
-
-
-
-
-
-
1
-
-
-
-
-
-
1
-
-
-
-
-
2
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
-
2
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
172049
Huang
Inhibition of N8-acetylspermid ...
Rattus sp.
J. Med. Chem.
35
2414-2418
1992
-
-
-
-
-
-
10
1
1
-
-
-
-
3
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
9
-
-
-
-
-
-
-
-
-
-
10
9
1
1
-
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
172046
Suzuke
-
Acetylspermidine deacetylase a ...
Homo sapiens
Med. Sci. Res.
15
675-676
1987
-
-
-
-
-
-
12
1
-
-
-
-
-
1
-
-
-
-
-
8
-
-
3
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
12
-
1
-
-
-
-
-
-
-
-
-
8
-
-
3
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
172050
Marchant
N1-Acetylspermidine is not a s ...
Rattus sp.
Biochim. Biophys. Acta
881
297-299
1986
-
-
-
-
-
-
2
-
1
-
-
-
-
1
-
-
-
-
-
1
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
2
-
-
1
-
-
-
-
-
-
-
-
1
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
172051
Manneh
-
Inhibitor studies on the chara ...
Rattus sp.
Proc. West. Pharmacol. Soc.
28
255-258
1985
-
-
-
-
-
-
7
1
1
-
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-
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1
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1
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1
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-
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-
-
-
-
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6
-
-
-
-
-
-
-
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7
6
1
1
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-
-
-
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-
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1
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1
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Libby
Acetylspermidine deacetylase ( ...
Rattus sp.
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1
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3
2
1
-
-
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1
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1
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1
1
1
3
-
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-
-
-
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1
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1
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4
-
2
1
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-
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1
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1
1
1
3
-
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1
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172053
Santacroce
Inhibition of acetylspermidine ...
Rattus sp.
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1
1
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1
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1
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1
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6
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9
6
1
1
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1
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1
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Blankenship
Deacetylation of N8-acetylsper ...
Rattus sp.
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1
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1
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1
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8
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1
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1
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1
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1
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1
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8
-
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1
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1
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1
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172055
Libby
Properties of an acetylspermid ...
Rattus sp.
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1
1
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3
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1
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2
1
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3
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1
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1
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3
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1
1
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1
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1
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1
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1
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