BRENDA - Enzyme Database
show all sequences of 1.14.13.44

Purification and characterization of 2-hydroxybiphenyl 3-monooxygenase, a novel NADH-dependent, FAD-containing aromatic hydroxylase from Pseudomonas azelaica HBP1

Suske, W.A.; Held, M.; Schmid, A.; Fleischmann, T.; Wubbolts, M.G.; Kohler, H.P.E.; J. Biol. Chem. 272, 24257-24265 (1997)

Data extracted from this reference:

Inhibitors
Inhibitors
Commentary
Organism
Structure
2,3-Dihydroxybiphenyl
inhibits reaction with 2-hydroxybiphenyl
Pseudomonas nitroreducens
AgNO3
0.01 mM, complete inhibition
Pseudomonas nitroreducens
CuSO4
0.01 mM, complete inhibition
Pseudomonas nitroreducens
FeSO4
0.08 mM, 30% inhibition
Pseudomonas nitroreducens
HgCl2
0.01 mM, complete inhibition
Pseudomonas nitroreducens
NaCl
10 mM, 36% inhibition. 100 mM, 89% inhibition
Pseudomonas nitroreducens
p-hydroxymercuribenzoate
partial protection in presence of 2-hydroxybiphenyl, reversed by excess of dithiothreitol
Pseudomonas nitroreducens
KM Value [mM]
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
0.0028
-
2-Hydroxybiphenyl
reaction with NADH and O2
Pseudomonas nitroreducens
0.0031
-
2-Hydroxybiphenyl
reaction with NADPH and O2
Pseudomonas nitroreducens
0.0034
-
2,2'-Dihydroxybiphenyl
reaction with NADPH and O2
Pseudomonas nitroreducens
0.004
-
2,2'-Dihydroxybiphenyl
reaction with NADH and O2
Pseudomonas nitroreducens
0.0057
-
2-sec-Butylphenol
reaction with NADH or NADPH and O2
Pseudomonas nitroreducens
0.0216
-
NADH
reaction with 2,2'-dihydroxybiphenyl and O2
Pseudomonas nitroreducens
0.0268
-
NADH
reaction with 2-hydroxybiphenyl and O2
Pseudomonas nitroreducens
0.0292
-
O2
reaction with 2-hydroxybiphenyl and NADH
Pseudomonas nitroreducens
0.0943
-
NADPH
reaction with 2,2'-dihydroxybiphenyl and O2
Pseudomonas nitroreducens
0.137
-
NADPH
reaction with 2-hydroxybiphenyl and O2
Pseudomonas nitroreducens
Molecular Weight [Da]
Molecular Weight [Da]
Molecular Weight Maximum [Da]
Commentary
Organism
60000
-
4 * 60000, SDS-PAGE
Pseudomonas nitroreducens
256000
-
gel filtration
Pseudomonas nitroreducens
Natural Substrates/ Products (Substrates)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
ID
2-hydroxybiphenyl + NADH + O2
Pseudomonas nitroreducens
first enzyme of 2-hydroxybiphenyl degradation
2,3-dihydroxybiphenyl + NAD+ + H2O
-
-
?
2-hydroxybiphenyl + NADH + O2
Pseudomonas nitroreducens HBP1
first enzyme of 2-hydroxybiphenyl degradation
2,3-dihydroxybiphenyl + NAD+ + H2O
-
-
?
Organism
Organism
UniProt
Commentary
Textmining
Pseudomonas nitroreducens
-
HBP1
-
Pseudomonas nitroreducens HBP1
-
HBP1
-
Purification (Commentary)
Purification (Commentary)
Organism
native and recombinant enzyme
Pseudomonas nitroreducens
Specific Activity [micromol/min/mg]
Specific Activity Minimum [µmol/min/mg]
Specific Activity Maximum [µmol/min/mg]
Commentary
Organism
additional information
-
-
Pseudomonas nitroreducens
Storage Stability
Storage Stability
Organism
-20°C, pure enzyme at concentration of 3.8 mg/ml in 50 mM phosphate buffer, pH 7.5, stable for at least 6 months
Pseudomonas nitroreducens
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
Substrate Product ID
2,2'-dihydroxybiphenyl + NADH + O2
-
438850
Pseudomonas nitroreducens
2,2',3-trihydroxybiphenyl + NAD+ + H2O
-
-
-
?
2,2'-dihydroxybiphenyl + NADPH + O2
-
438850
Pseudomonas nitroreducens
2,2',3-trihydroxybiphenyl + NADP+ + H2O
-
-
-
?
2,5-dihydroxybiphenyl + NADH + O2
-
438850
Pseudomonas nitroreducens
2,3,5-trihydroxybiphenyl + NAD+ + H2O
-
-
-
?
2-ethylphenol + NADH + O2
-
438850
Pseudomonas nitroreducens
1,2-dihydroxy-3-ethylbenzene + NAD+ + H2O
-
-
-
?
2-hydroxybiphenyl + NADH + O2
-
438850
Pseudomonas nitroreducens
2,3-dihydroxybiphenyl + NAD+ + H2O
-
438850
Pseudomonas nitroreducens
?
2-hydroxybiphenyl + NADH + O2
first enzyme of 2-hydroxybiphenyl degradation
438850
Pseudomonas nitroreducens
2,3-dihydroxybiphenyl + NAD+ + H2O
-
-
-
?
2-hydroxybiphenyl + NADH + O2
-
438850
Pseudomonas nitroreducens HBP1
2,3-dihydroxybiphenyl + NAD+ + H2O
-
438850
Pseudomonas nitroreducens HBP1
?
2-hydroxybiphenyl + NADH + O2
first enzyme of 2-hydroxybiphenyl degradation
438850
Pseudomonas nitroreducens HBP1
2,3-dihydroxybiphenyl + NAD+ + H2O
-
-
-
?
2-hydroxybiphenyl + NADPH + O2
-
438850
Pseudomonas nitroreducens
2,3-dihydroxybiphenyl + NADP+ + H2O
-
-
-
?
2-hydroxybiphenyl + NADPH + O2
-
438850
Pseudomonas nitroreducens HBP1
2,3-dihydroxybiphenyl + NADP+ + H2O
-
-
-
?
2-methylphenol + NADH + O2
-
438850
Pseudomonas nitroreducens
1,2-dihydroxy-3-methylbenzene + NAD+ + H2O
-
-
-
?
2-propylphenol + NADH + O2
-
438850
Pseudomonas nitroreducens
1,2-dihydroxy-3-propylbenzene + NAD+ + H2O
-
-
-
?
2-propylphenol + NADH + O2
-
438850
Pseudomonas nitroreducens HBP1
1,2-dihydroxy-3-propylbenzene + NAD+ + H2O
-
-
-
?
2-sec-butylphenol + NADH + O2
-
438850
Pseudomonas nitroreducens
2-sec-butylcatechol + NAD+ + H2O
-
-
-
?
2-sec-butylphenol + NADPH + O2
-
438850
Pseudomonas nitroreducens
2-sec-butylcatechol + NADP+ + H2O
-
-
-
?
2-tert-butylphenol + NADH + O2
-
438850
Pseudomonas nitroreducens
1,2-dihydroxy-3-tert-butylbenzene + NAD+ + H2O
-
-
-
?
additional information
the substrates partially uncouple oxygen activation from hydroxylation with resultant reduction of both atoms of oxygen to form hydrogen peroxide
438850
Pseudomonas nitroreducens
?
-
-
-
?
additional information
the substrates partially uncouple oxygen activation from hydroxylation with resultant reduction of both atoms of oxygen to form hydrogen peroxide
438850
Pseudomonas nitroreducens HBP1
?
-
-
-
?
Subunits
Subunits
Commentary
Organism
tetramer
4 * 60000, SDS-PAGE
Pseudomonas nitroreducens
Turnover Number [1/s]
Turnover Number Minimum [1/s]
Turnover Number Maximum [1/s]
Substrate
Commentary
Organism
Structure
9
-
2,2'-Dihydroxybiphenyl
reaction with NADH and O2
Pseudomonas nitroreducens
9.4
-
2,2'-Dihydroxybiphenyl
reaction with NADPH and O2
Pseudomonas nitroreducens
9.8
-
NADH
reaction with 2,2'-dihydroxybiphenyl and O2
Pseudomonas nitroreducens
10.2
-
2-sec-Butylphenol
reaction with NADPH and O2
Pseudomonas nitroreducens
11.2
-
NADPH
reaction with 2,2'-dihydroxybiphenyl and O2
Pseudomonas nitroreducens
12.8
-
2-Hydroxybiphenyl
reaction with NADPH and O2
Pseudomonas nitroreducens
14.9
-
2-Hydroxybiphenyl
reaction with NADH and O2
Pseudomonas nitroreducens
15.8
-
2-sec-Butylphenol
reaction with NADH and O2
Pseudomonas nitroreducens
16.2
-
NADH
reaction with 2-hydroxybiphenyl and O2
Pseudomonas nitroreducens
16.2
-
O2
reaction with 2-hydroxybiphenyl and NADH
Pseudomonas nitroreducens
18.8
-
NADPH
reaction with 2-hydroxybiphenyl and O2
Pseudomonas nitroreducens
pH Optimum
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
7.5
-
-
Pseudomonas nitroreducens
pH Range
pH Minimum
pH Maximum
Commentary
Organism
7.2
7.8
more than 80% of maximal activity at pH 7.2 and pH 7.8, beyond pH 7.8 activity declines abruptly with increasing pH
Pseudomonas nitroreducens
Cofactor
Cofactor
Commentary
Organism
Structure
FAD
one molecule of noncovalently bound FAD per subunit
Pseudomonas nitroreducens
NADH
-
Pseudomonas nitroreducens
NADPH
can replace NADH as electron donor, Km-value for NADPH is much higher than for NADH
Pseudomonas nitroreducens
Ki Value [mM]
Ki Value [mM]
Ki Value maximum [mM]
Inhibitor
Commentary
Organism
Structure
0.9
-
2,3-Dihydroxybiphenyl
-
Pseudomonas nitroreducens
Cofactor (protein specific)
Cofactor
Commentary
Organism
Structure
FAD
one molecule of noncovalently bound FAD per subunit
Pseudomonas nitroreducens
NADH
-
Pseudomonas nitroreducens
NADPH
can replace NADH as electron donor, Km-value for NADPH is much higher than for NADH
Pseudomonas nitroreducens
Inhibitors (protein specific)
Inhibitors
Commentary
Organism
Structure
2,3-Dihydroxybiphenyl
inhibits reaction with 2-hydroxybiphenyl
Pseudomonas nitroreducens
AgNO3
0.01 mM, complete inhibition
Pseudomonas nitroreducens
CuSO4
0.01 mM, complete inhibition
Pseudomonas nitroreducens
FeSO4
0.08 mM, 30% inhibition
Pseudomonas nitroreducens
HgCl2
0.01 mM, complete inhibition
Pseudomonas nitroreducens
NaCl
10 mM, 36% inhibition. 100 mM, 89% inhibition
Pseudomonas nitroreducens
p-hydroxymercuribenzoate
partial protection in presence of 2-hydroxybiphenyl, reversed by excess of dithiothreitol
Pseudomonas nitroreducens
Ki Value [mM] (protein specific)
Ki Value [mM]
Ki Value maximum [mM]
Inhibitor
Commentary
Organism
Structure
0.9
-
2,3-Dihydroxybiphenyl
-
Pseudomonas nitroreducens
KM Value [mM] (protein specific)
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
0.0028
-
2-Hydroxybiphenyl
reaction with NADH and O2
Pseudomonas nitroreducens
0.0031
-
2-Hydroxybiphenyl
reaction with NADPH and O2
Pseudomonas nitroreducens
0.0034
-
2,2'-Dihydroxybiphenyl
reaction with NADPH and O2
Pseudomonas nitroreducens
0.004
-
2,2'-Dihydroxybiphenyl
reaction with NADH and O2
Pseudomonas nitroreducens
0.0057
-
2-sec-Butylphenol
reaction with NADH or NADPH and O2
Pseudomonas nitroreducens
0.0216
-
NADH
reaction with 2,2'-dihydroxybiphenyl and O2
Pseudomonas nitroreducens
0.0268
-
NADH
reaction with 2-hydroxybiphenyl and O2
Pseudomonas nitroreducens
0.0292
-
O2
reaction with 2-hydroxybiphenyl and NADH
Pseudomonas nitroreducens
0.0943
-
NADPH
reaction with 2,2'-dihydroxybiphenyl and O2
Pseudomonas nitroreducens
0.137
-
NADPH
reaction with 2-hydroxybiphenyl and O2
Pseudomonas nitroreducens
Molecular Weight [Da] (protein specific)
Molecular Weight [Da]
Molecular Weight Maximum [Da]
Commentary
Organism
60000
-
4 * 60000, SDS-PAGE
Pseudomonas nitroreducens
256000
-
gel filtration
Pseudomonas nitroreducens
Natural Substrates/ Products (Substrates) (protein specific)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
ID
2-hydroxybiphenyl + NADH + O2
Pseudomonas nitroreducens
first enzyme of 2-hydroxybiphenyl degradation
2,3-dihydroxybiphenyl + NAD+ + H2O
-
-
?
2-hydroxybiphenyl + NADH + O2
Pseudomonas nitroreducens HBP1
first enzyme of 2-hydroxybiphenyl degradation
2,3-dihydroxybiphenyl + NAD+ + H2O
-
-
?
Purification (Commentary) (protein specific)
Commentary
Organism
native and recombinant enzyme
Pseudomonas nitroreducens
Specific Activity [micromol/min/mg] (protein specific)
Specific Activity Minimum [µmol/min/mg]
Specific Activity Maximum [µmol/min/mg]
Commentary
Organism
additional information
-
-
Pseudomonas nitroreducens
Storage Stability (protein specific)
Storage Stability
Organism
-20°C, pure enzyme at concentration of 3.8 mg/ml in 50 mM phosphate buffer, pH 7.5, stable for at least 6 months
Pseudomonas nitroreducens
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
ID
2,2'-dihydroxybiphenyl + NADH + O2
-
438850
Pseudomonas nitroreducens
2,2',3-trihydroxybiphenyl + NAD+ + H2O
-
-
-
?
2,2'-dihydroxybiphenyl + NADPH + O2
-
438850
Pseudomonas nitroreducens
2,2',3-trihydroxybiphenyl + NADP+ + H2O
-
-
-
?
2,5-dihydroxybiphenyl + NADH + O2
-
438850
Pseudomonas nitroreducens
2,3,5-trihydroxybiphenyl + NAD+ + H2O
-
-
-
?
2-ethylphenol + NADH + O2
-
438850
Pseudomonas nitroreducens
1,2-dihydroxy-3-ethylbenzene + NAD+ + H2O
-
-
-
?
2-hydroxybiphenyl + NADH + O2
-
438850
Pseudomonas nitroreducens
2,3-dihydroxybiphenyl + NAD+ + H2O
-
438850
Pseudomonas nitroreducens
?
2-hydroxybiphenyl + NADH + O2
first enzyme of 2-hydroxybiphenyl degradation
438850
Pseudomonas nitroreducens
2,3-dihydroxybiphenyl + NAD+ + H2O
-
-
-
?
2-hydroxybiphenyl + NADH + O2
-
438850
Pseudomonas nitroreducens HBP1
2,3-dihydroxybiphenyl + NAD+ + H2O
-
438850
Pseudomonas nitroreducens HBP1
?
2-hydroxybiphenyl + NADH + O2
first enzyme of 2-hydroxybiphenyl degradation
438850
Pseudomonas nitroreducens HBP1
2,3-dihydroxybiphenyl + NAD+ + H2O
-
-
-
?
2-hydroxybiphenyl + NADPH + O2
-
438850
Pseudomonas nitroreducens
2,3-dihydroxybiphenyl + NADP+ + H2O
-
-
-
?
2-hydroxybiphenyl + NADPH + O2
-
438850
Pseudomonas nitroreducens HBP1
2,3-dihydroxybiphenyl + NADP+ + H2O
-
-
-
?
2-methylphenol + NADH + O2
-
438850
Pseudomonas nitroreducens
1,2-dihydroxy-3-methylbenzene + NAD+ + H2O
-
-
-
?
2-propylphenol + NADH + O2
-
438850
Pseudomonas nitroreducens
1,2-dihydroxy-3-propylbenzene + NAD+ + H2O
-
-
-
?
2-propylphenol + NADH + O2
-
438850
Pseudomonas nitroreducens HBP1
1,2-dihydroxy-3-propylbenzene + NAD+ + H2O
-
-
-
?
2-sec-butylphenol + NADH + O2
-
438850
Pseudomonas nitroreducens
2-sec-butylcatechol + NAD+ + H2O
-
-
-
?
2-sec-butylphenol + NADPH + O2
-
438850
Pseudomonas nitroreducens
2-sec-butylcatechol + NADP+ + H2O
-
-
-
?
2-tert-butylphenol + NADH + O2
-
438850
Pseudomonas nitroreducens
1,2-dihydroxy-3-tert-butylbenzene + NAD+ + H2O
-
-
-
?
additional information
the substrates partially uncouple oxygen activation from hydroxylation with resultant reduction of both atoms of oxygen to form hydrogen peroxide
438850
Pseudomonas nitroreducens
?
-
-
-
?
additional information
the substrates partially uncouple oxygen activation from hydroxylation with resultant reduction of both atoms of oxygen to form hydrogen peroxide
438850
Pseudomonas nitroreducens HBP1
?
-
-
-
?
Subunits (protein specific)
Subunits
Commentary
Organism
tetramer
4 * 60000, SDS-PAGE
Pseudomonas nitroreducens
Turnover Number [1/s] (protein specific)
Turnover Number Minimum [1/s]
Turnover Number Maximum [1/s]
Substrate
Commentary
Organism
Structure
9
-
2,2'-Dihydroxybiphenyl
reaction with NADH and O2
Pseudomonas nitroreducens
9.4
-
2,2'-Dihydroxybiphenyl
reaction with NADPH and O2
Pseudomonas nitroreducens
9.8
-
NADH
reaction with 2,2'-dihydroxybiphenyl and O2
Pseudomonas nitroreducens
10.2
-
2-sec-Butylphenol
reaction with NADPH and O2
Pseudomonas nitroreducens
11.2
-
NADPH
reaction with 2,2'-dihydroxybiphenyl and O2
Pseudomonas nitroreducens
12.8
-
2-Hydroxybiphenyl
reaction with NADPH and O2
Pseudomonas nitroreducens
14.9
-
2-Hydroxybiphenyl
reaction with NADH and O2
Pseudomonas nitroreducens
15.8
-
2-sec-Butylphenol
reaction with NADH and O2
Pseudomonas nitroreducens
16.2
-
NADH
reaction with 2-hydroxybiphenyl and O2
Pseudomonas nitroreducens
16.2
-
O2
reaction with 2-hydroxybiphenyl and NADH
Pseudomonas nitroreducens
18.8
-
NADPH
reaction with 2-hydroxybiphenyl and O2
Pseudomonas nitroreducens
pH Optimum (protein specific)
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
7.5
-
-
Pseudomonas nitroreducens
pH Range (protein specific)
pH Minimum
pH Maximum
Commentary
Organism
7.2
7.8
more than 80% of maximal activity at pH 7.2 and pH 7.8, beyond pH 7.8 activity declines abruptly with increasing pH
Pseudomonas nitroreducens
Other publictions for EC 1.14.13.44
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)
744407
Kanteev
A crystal structure of 2-hydr ...
Pseudomonas nitroreducens
Biochim. Biophys. Acta
1854
1906-1913
2015
-
-
1
1
6
-
-
12
-
-
-
-
-
5
-
-
1
-
-
-
-
-
2
-
2
-
-
-
12
-
-
-
1
-
-
-
-
-
1
1
1
6
-
-
-
-
12
-
-
-
-
-
-
-
1
-
-
-
-
2
-
-
-
-
12
-
-
-
-
-
-
-
-
12
12
744702
Jensen
Structures of the Apo and FAD ...
Pseudomonas nitroreducens
ChemBioChem
16
968-976
2015
-
-
1
1
-
-
-
4
-
-
-
-
-
3
-
-
1
-
-
-
-
-
1
1
1
-
-
-
-
1
-
-
1
-
-
-
-
-
1
1
1
-
-
-
-
-
4
-
-
-
-
-
-
-
1
-
-
-
-
1
1
-
-
-
-
1
-
-
-
-
-
-
-
-
-
657455
Meyer
Crystallization and preliminar ...
Pseudomonas nitroreducens
Acta Crystallogr. Sect. D
59
741-743
2003
-
-
1
1
-
-
3
-
-
-
1
1
-
7
-
-
1
-
-
-
-
-
2
1
1
-
-
-
-
-
-
-
2
-
-
-
-
-
1
2
1
-
-
-
3
-
-
-
-
1
1
-
-
-
1
-
-
-
-
2
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
438847
Meyer
Changing the substrate reactiv ...
Pseudomonas nitroreducens, Pseudomonas nitroreducens HBP1
J. Biol. Chem.
277
5575-5582
2002
-
-
-
-
2
-
-
1
-
-
-
-
-
10
-
-
-
-
-
-
-
-
10
-
-
-
-
-
4
-
-
-
2
-
-
-
-
-
-
2
-
2
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
10
-
-
-
-
4
-
-
-
-
-
-
-
-
-
-
438848
Meyer
Hydroxylation of indole by lab ...
Pseudomonas nitroreducens, Pseudomonas nitroreducens HBP1
J. Biol. Chem.
277
34161-34167
2002
-
-
-
-
1
-
-
-
-
-
-
-
-
10
-
-
-
-
-
-
-
-
6
-
-
-
-
-
4
-
-
-
1
-
-
-
-
-
-
1
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
6
-
-
-
-
4
-
-
-
-
-
-
-
-
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2
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10
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1
1
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8
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1
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2
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2
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2
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1
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8
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1
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1
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12
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2
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1
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1
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1
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1
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2
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1
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7
10
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2
2
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16
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1
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1
1
18
1
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11
1
1
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3
1
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3
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7
1
10
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2
2
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1
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1
1
18
1
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11
1
1
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