BRENDA - Enzyme Database show
show all sequences of 1.14.11.21

Synthesis and reaction of potential alternate substrates and mechanism-based inhibitors of clavaminate synthase

Iwata-Reuyl, D.; Basak, A.; Silverman, L.S.; Engle, C.A.; Townsend, C.A.; J. Nat. Prod. 56, 1373-1396 (1993)

Data extracted from this reference:

Inhibitors
Inhibitors
Commentary
Organism
Structure
4'-ethynyl proclavaminate
noncompetitive
Streptomyces clavuligerus
4'-vinyl proclavaminate
noncompetitive
Streptomyces clavuligerus
4-cyclopropyl proclavaminate
noncompetitive
Streptomyces clavuligerus
KM Value [mM]
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
0.23
-
N-alpha-acetyl-L-arginine
pH 7.0, 22°C
Streptomyces clavuligerus
Metals/Ions
Metals/Ions
Commentary
Organism
Structure
Fe2+
required
Streptomyces clavuligerus
Organism
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
Streptomyces clavuligerus
-
strain ATCC 27064
-
Reaction
Reaction
Commentary
Organism
dihydroclavaminate + 2-oxoglutarate + O2 = clavaminate + succinate + CO2 + H2O
reaction mechanism
Streptomyces clavuligerus
proclavaminate + 2-oxoglutarate + O2 = dihydroclavaminate + succinate + CO2 + H2O
reaction mechanism
Streptomyces clavuligerus
Specific Activity [micromol/min/mg]
Specific Activity Minimum [µmol/min/mg]
Specific Activity Maximum [µmol/min/mg]
Commentary
Organism
0.4
-
65fold purified enzyme
Streptomyces clavuligerus
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
deoxyamidinoproclavaminate + 2-oxoglutarate + O2
-
639273
Streptomyces clavuligerus
amidinoproclavaminate + succinate + CO2 + H2O
10% of the product is proclavaminate, 90% of the product is E-(2S)-5-amino-2(2'-oxoazetidin-1-yl)-pent-3,4-enoate
639273
Streptomyces clavuligerus
?
deoxyamidinoproclavaminate + 2-oxoglutarate + O2
isozyme CS2
639273
Streptomyces clavuligerus
E-(2S)-5-amino-2(2'-oxoazetidin-1-yl)-pent-3,4-enoate + succinate + CO2 + H2O
10% of the product is proclavaminate, 90% of the product is E-(2S)-5-amino-2(2'-oxoazetidin-1-yl)-pent-3,4-enoate
639273
Streptomyces clavuligerus
?
dihydroclavaminate + 2-oxoglutarate + O2
stereochemical course of oxygen insertion
639273
Streptomyces clavuligerus
clavaminate + succinate + CO2 + H2O
-
639273
Streptomyces clavuligerus
?
dihydroclavaminate + 2-oxoglutarate + O2
cyclization
639273
Streptomyces clavuligerus
clavaminate + succinate + CO2 + H2O
-
639273
Streptomyces clavuligerus
?
additional information
specific for 2-oxoglutarate
639273
Streptomyces clavuligerus
?
-
-
-
-
additional information
4'-vinyl proclavaminate, 4'-ethynyl proclavaminate, and 4-cyclopropyl proclavaminate are no substrates
639273
Streptomyces clavuligerus
?
-
-
-
-
N-alpha-acetyl-L-arginine + 2-oxoglutarate + O2
hydroxylation
639273
Streptomyces clavuligerus
4-hydroxy-N-alpha-acetyl-L-arginine + succinate + CO2 + H2O
-
639273
Streptomyces clavuligerus
?
N-alpha-acetyl-L-arginine + 2-oxoglutarate + O2
isozyme CS2
639273
Streptomyces clavuligerus
4-hydroxy-N-alpha-acetyl-L-arginine + succinate + CO2 + H2O
-
639273
Streptomyces clavuligerus
?
proclavaminate + 2-oxoglutarate + O2
(4'RS)-rac-proclavaminate
639273
Streptomyces clavuligerus
dihydroclavaminate + succinate + CO2 + H2O
-
639273
Streptomyces clavuligerus
?
proclavaminate + 2-oxoglutarate + O2
saturation
639273
Streptomyces clavuligerus
dihydroclavaminate + succinate + CO2 + H2O
-
639273
Streptomyces clavuligerus
?
proclavaminate + 2-oxoglutarate + O2
stereochemical course of oxygen insertion
639273
Streptomyces clavuligerus
dihydroclavaminate + succinate + CO2 + H2O
-
639273
Streptomyces clavuligerus
?
Temperature Optimum [°C]
Temperature Optimum [°C]
Temperature Optimum Maximum [°C]
Commentary
Organism
22
-
room temperature, assay at
Streptomyces clavuligerus
Turnover Number [1/s]
Turnover Number Minimum [1/s]
Turnover Number Maximum [1/s]
Substrate
Commentary
Organism
Structure
6.4
-
N-alpha-acetyl-L-arginine
pH 7.0, 22°C
Streptomyces clavuligerus
pH Optimum
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
7
-
assay at
Streptomyces clavuligerus
Ki Value [mM]
Ki Value [mM]
Ki Value maximum [mM]
Inhibitor
Commentary
Organism
Structure
additional information
-
additional information
Ki of 4'-vinyl proclavaminate, 4'-ethynyl proclavaminate, and 4-cyclopropyl proclavaminate is in the range of 2-10 mM
Streptomyces clavuligerus
Inhibitors (protein specific)
Inhibitors
Commentary
Organism
Structure
4'-ethynyl proclavaminate
noncompetitive
Streptomyces clavuligerus
4'-vinyl proclavaminate
noncompetitive
Streptomyces clavuligerus
4-cyclopropyl proclavaminate
noncompetitive
Streptomyces clavuligerus
Ki Value [mM] (protein specific)
Ki Value [mM]
Ki Value maximum [mM]
Inhibitor
Commentary
Organism
Structure
additional information
-
additional information
Ki of 4'-vinyl proclavaminate, 4'-ethynyl proclavaminate, and 4-cyclopropyl proclavaminate is in the range of 2-10 mM
Streptomyces clavuligerus
KM Value [mM] (protein specific)
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
0.23
-
N-alpha-acetyl-L-arginine
pH 7.0, 22°C
Streptomyces clavuligerus
Metals/Ions (protein specific)
Metals/Ions
Commentary
Organism
Structure
Fe2+
required
Streptomyces clavuligerus
Specific Activity [micromol/min/mg] (protein specific)
Specific Activity Minimum [µmol/min/mg]
Specific Activity Maximum [µmol/min/mg]
Commentary
Organism
0.4
-
65fold purified enzyme
Streptomyces clavuligerus
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
deoxyamidinoproclavaminate + 2-oxoglutarate + O2
-
639273
Streptomyces clavuligerus
amidinoproclavaminate + succinate + CO2 + H2O
10% of the product is proclavaminate, 90% of the product is E-(2S)-5-amino-2(2'-oxoazetidin-1-yl)-pent-3,4-enoate
639273
Streptomyces clavuligerus
?
deoxyamidinoproclavaminate + 2-oxoglutarate + O2
isozyme CS2
639273
Streptomyces clavuligerus
E-(2S)-5-amino-2(2'-oxoazetidin-1-yl)-pent-3,4-enoate + succinate + CO2 + H2O
10% of the product is proclavaminate, 90% of the product is E-(2S)-5-amino-2(2'-oxoazetidin-1-yl)-pent-3,4-enoate
639273
Streptomyces clavuligerus
?
dihydroclavaminate + 2-oxoglutarate + O2
stereochemical course of oxygen insertion
639273
Streptomyces clavuligerus
clavaminate + succinate + CO2 + H2O
-
639273
Streptomyces clavuligerus
?
dihydroclavaminate + 2-oxoglutarate + O2
cyclization
639273
Streptomyces clavuligerus
clavaminate + succinate + CO2 + H2O
-
639273
Streptomyces clavuligerus
?
additional information
specific for 2-oxoglutarate
639273
Streptomyces clavuligerus
?
-
-
-
-
additional information
4'-vinyl proclavaminate, 4'-ethynyl proclavaminate, and 4-cyclopropyl proclavaminate are no substrates
639273
Streptomyces clavuligerus
?
-
-
-
-
N-alpha-acetyl-L-arginine + 2-oxoglutarate + O2
hydroxylation
639273
Streptomyces clavuligerus
4-hydroxy-N-alpha-acetyl-L-arginine + succinate + CO2 + H2O
-
639273
Streptomyces clavuligerus
?
N-alpha-acetyl-L-arginine + 2-oxoglutarate + O2
isozyme CS2
639273
Streptomyces clavuligerus
4-hydroxy-N-alpha-acetyl-L-arginine + succinate + CO2 + H2O
-
639273
Streptomyces clavuligerus
?
proclavaminate + 2-oxoglutarate + O2
(4'RS)-rac-proclavaminate
639273
Streptomyces clavuligerus
dihydroclavaminate + succinate + CO2 + H2O
-
639273
Streptomyces clavuligerus
?
proclavaminate + 2-oxoglutarate + O2
saturation
639273
Streptomyces clavuligerus
dihydroclavaminate + succinate + CO2 + H2O
-
639273
Streptomyces clavuligerus
?
proclavaminate + 2-oxoglutarate + O2
stereochemical course of oxygen insertion
639273
Streptomyces clavuligerus
dihydroclavaminate + succinate + CO2 + H2O
-
639273
Streptomyces clavuligerus
?
Temperature Optimum [°C] (protein specific)
Temperature Optimum [°C]
Temperature Optimum Maximum [°C]
Commentary
Organism
22
-
room temperature, assay at
Streptomyces clavuligerus
Turnover Number [1/s] (protein specific)
Turnover Number Minimum [1/s]
Turnover Number Maximum [1/s]
Substrate
Commentary
Organism
Structure
6.4
-
N-alpha-acetyl-L-arginine
pH 7.0, 22°C
Streptomyces clavuligerus
pH Optimum (protein specific)
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
7
-
assay at
Streptomyces clavuligerus
Other publictions for EC 1.14.11.21
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
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)
742159
Shrestha
-
Heterologous production of cl ...
Streptomyces clavuligerus
Biotechnol. Bioprocess Eng.
22
359-365
2017
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723902
Chin
-
Predicting the catalytic sites ...
Streptomyces clavuligerus
Afr. J. Microbiol. Res.
5
3357-3366
2011
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2
4
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685142
Borowski
Mechanism for cyclization reac ...
Streptomyces clavuligerus
Biochemistry
46
3682-3691
2007
-
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1
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639036
Townsend
New reactions in clavulanic ac ...
Streptomyces clavuligerus
Curr. Opin. Chem. Biol.
6
583-589
2002
-
-
-
-
-
-
-
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1
-
4
-
1
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1
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9
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9
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639286
Zhang
Crystal structure of a clavami ...
Streptomyces clavuligerus
FEBS Lett.
517
7-12
2002
-
-
-
1
-
-
-
-
-
1
-
4
-
1
-
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3
-
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9
-
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1
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1
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4
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9
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639284
Zhou
Spectroscopic studies of subst ...
Streptomyces clavuligerus
J. Am. Chem. Soc.
123
7388-7398
2001
-
-
-
-
-
-
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1
-
4
-
1
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2
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11
-
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1
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4
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11
-
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639281
Zhang
Structural origins of the sele ...
Streptomyces clavuligerus
Nat. Struct. Biol.
7
127-133
2000
-
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1
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1
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1
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2
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8
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1
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8
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639282
Khaleeli
Site-directed mutagenesis and ...
Streptomyces clavuligerus
Biochemistry
39
8666-8673
2000
-
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1
-
8
-
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1
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1
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1
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3
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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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3
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1
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1
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639283
Doan
Mutagenesis studies on the iro ...
Streptomyces clavuligerus
Biochem. Biophys. Res. Commun.
279
240-244
2000
-
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15
-
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1
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1
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2
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5
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15
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1
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5
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639280
Lloyd
-
Product-substrate engineering ...
Streptomyces clavuligerus
Tetrahedron
55
10201-10220
1999
-
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1
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4
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1
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11
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11
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639279
Zhou
-
Substrate binding to the alpha ...
Streptomyces clavuligerus
J. Am. Chem. Soc.
120
13539-13540
1998
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639278
Baldwin
-
Chemo-enzymic synthesis of bic ...
Streptomyces clavuligerus
Tetrahedron
53
7011-7020
1997
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1
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639277
Busby
A single monomeric iron center ...
Streptomyces clavuligerus
Bioorg. Med. Chem.
4
1059-1064
1996
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1
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2
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1
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5
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1
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3
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11
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1
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1
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2
1
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1
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5
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11
-
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639274
Janc
Purification and characterizat ...
Streptomyces antibioticus, Streptomyces antibioticus Tu1718, Streptomyces clavuligerus
J. Biol. Chem.
270
5399-5404
1995
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3
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2
6
15
-
5
1
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1
6
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1
1
31
2
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2
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2
6
15
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1
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1
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1
1
31
2
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2
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639275
Busby
Expression and purification of ...
Streptomyces clavuligerus
J. Biol. Chem.
270
4262-4269
1995
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1
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1
3
2
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1
2
1
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3
1
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1
2
-
-
2
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6
-
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1
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1
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1
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3
-
2
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