BRENDA - Enzyme Database
show all sequences of 1.13.11.60

7,8- and 5,8-linoleate diol synthases support the heterolytic scission of oxygen-oxygen bonds by different amide residues

Hoffmann, I.; Oliw, E.H.; Arch. Biochem. Biophys. 539, 87-91 (2013)

Data extracted from this reference:

Cloned(Commentary)
Cloned (Commentary)
Organism
expression of wild-type and mutant enzymes in Escherichia coli strain BL21
Aspergillus fumigatus
expression of wild-type and mutant enzymes in Escherichia coli strain BL21
Gaeumannomyces graminis
Engineering
Protein Variants
Commentary
Organism
N887L
site-directed mutagenesis, the mutant retains (5S,8R)-5,8-dihydroxylinoleate as the main metabolite with an increased formation of 6,8- and 8,11-dihydroxylinoleate
Aspergillus fumigatus
N887Q
site-directed mutagenesis, the mutant retains (5S,8R)-5,8-dihydroxylinoleate as the main metabolite with an increased formation of 6,8- and 8,11-dihydroxylinoleate
Aspergillus fumigatus
N938D
site-directed mutagenesis, the mutation of the 7,8-linoleate diol synthase reduces the hydroperoxide isomerase activity of the enzyme
Gaeumannomyces graminis
N938L
site-directed mutagenesis, the mutation of the 7,8-linoleate diol synthase abolishes the hydroperoxide isomerase activity of the enzyme
Gaeumannomyces graminis
N938Q
site-directed mutagenesis, the mutation of the 7,8-linoleate diol synthase reduces the hydroperoxide isomerase activity of the enzyme
Gaeumannomyces graminis
Q890E
site-directed mutagenesis, the mutant retains (5S,8R)-5,8-dihydroxylinoleate as the main product, but shifts oxygenation from C-5 to C-7 and C-11 and to formation of epoxyalcohols by homolytic scission of (8R)-hydroperoxylinoleic acid
Aspergillus fumigatus
Q890L
site-directed mutagenesis, the mutant shows almost abolished 5,8-linoleate diol synthase activity
Aspergillus fumigatus
Organism
Organism
UniProt
Commentary
Textmining
Aspergillus fumigatus
-
-
-
Gaeumannomyces graminis
-
-
-
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
Substrate Product ID
linoleate + O2
-
724132
Aspergillus fumigatus
(8R,9Z,12Z)-8-hydroperoxyoctadeca-9,12-dienoate
-
-
-
?
linoleate + O2
-
724132
Gaeumannomyces graminis
(8R,9Z,12Z)-8-hydroperoxyoctadeca-9,12-dienoate
-
-
-
?
additional information
the bifunctional enzyme forms (7S,8S)-7,8-dihydroxylinoleic acid from (8R)-hydroperoxylinoleic acid by intramolecular oxygen transfer. Linoleate diol synthases are fungal dioxygenase-cytochrome P450 fusion enzymes. P450 hydroxylases usually contain an acid-alcohol pair in the I-helices for the heterolytic scission of O2 and formation of compound I, i.e. Por+-Fe(IV)=O, and water. The function of the acid-alcohol pair appears to be replaced by a different amide residue, Asn938 of 7,8-LDS, for heterolysis of (8R,9Z,12Z)-8-hydroperoxyoctadeca-9,12-dienoate to generate compound I
724132
Gaeumannomyces graminis
?
-
-
-
-
additional information
the bifunctional enzyme forms 5S,8S-dihydroxylinoleic acid from (8R)-hydroperoxylinoleic acid by intramolecular oxygen transfer. Linoleate diol synthases are fungal dioxygenase-cytochrome P450 fusion enzymes. P450 hydroxylases usually contain an acid-alcohol pair in the I-helices for the heterolytic scission of O2 and formation of compound I, i.e. Por+-Fe(IV)=O, and water. The function of the acid-alcohol pair appears to be replaced by a different amide residue, Gln890 of 5,8-LDS, for heterolysis of (8R,9Z,12Z)-8-hydroperoxyoctadeca-9,12-dienoate to generate compound I
724132
Aspergillus fumigatus
?
-
-
-
-
additional information
the enzyme forms (5S,8R)-5,8-dihydroxylinoleic acid from (8R)-hydroperoxylinoleic acid by intramolecular oxygen transfer. Linoleate diol synthases are fungal dioxygenase-cytochrome P450 fusion enzymes
724132
Aspergillus fumigatus
?
-
-
-
-
Subunits
Subunits
Commentary
Organism
More
homology model of 5,8-LDS, overview
Aspergillus fumigatus
More
homology model of 7,8-LDS, overview
Gaeumannomyces graminis
Synonyms
Synonyms
Commentary
Organism
5,8-LDS
-
Aspergillus fumigatus
5,8-linoleate diol synthase
-
Aspergillus fumigatus
7,8-LDS
-
Gaeumannomyces graminis
7,8-linoleate diol synthase
-
Gaeumannomyces graminis
Cloned(Commentary) (protein specific)
Commentary
Organism
expression of wild-type and mutant enzymes in Escherichia coli strain BL21
Aspergillus fumigatus
expression of wild-type and mutant enzymes in Escherichia coli strain BL21
Gaeumannomyces graminis
Engineering (protein specific)
Protein Variants
Commentary
Organism
N887L
site-directed mutagenesis, the mutant retains (5S,8R)-5,8-dihydroxylinoleate as the main metabolite with an increased formation of 6,8- and 8,11-dihydroxylinoleate
Aspergillus fumigatus
N887Q
site-directed mutagenesis, the mutant retains (5S,8R)-5,8-dihydroxylinoleate as the main metabolite with an increased formation of 6,8- and 8,11-dihydroxylinoleate
Aspergillus fumigatus
N938D
site-directed mutagenesis, the mutation of the 7,8-linoleate diol synthase reduces the hydroperoxide isomerase activity of the enzyme
Gaeumannomyces graminis
N938L
site-directed mutagenesis, the mutation of the 7,8-linoleate diol synthase abolishes the hydroperoxide isomerase activity of the enzyme
Gaeumannomyces graminis
N938Q
site-directed mutagenesis, the mutation of the 7,8-linoleate diol synthase reduces the hydroperoxide isomerase activity of the enzyme
Gaeumannomyces graminis
Q890E
site-directed mutagenesis, the mutant retains (5S,8R)-5,8-dihydroxylinoleate as the main product, but shifts oxygenation from C-5 to C-7 and C-11 and to formation of epoxyalcohols by homolytic scission of (8R)-hydroperoxylinoleic acid
Aspergillus fumigatus
Q890L
site-directed mutagenesis, the mutant shows almost abolished 5,8-linoleate diol synthase activity
Aspergillus fumigatus
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
ID
linoleate + O2
-
724132
Aspergillus fumigatus
(8R,9Z,12Z)-8-hydroperoxyoctadeca-9,12-dienoate
-
-
-
?
linoleate + O2
-
724132
Gaeumannomyces graminis
(8R,9Z,12Z)-8-hydroperoxyoctadeca-9,12-dienoate
-
-
-
?
additional information
the bifunctional enzyme forms (7S,8S)-7,8-dihydroxylinoleic acid from (8R)-hydroperoxylinoleic acid by intramolecular oxygen transfer. Linoleate diol synthases are fungal dioxygenase-cytochrome P450 fusion enzymes. P450 hydroxylases usually contain an acid-alcohol pair in the I-helices for the heterolytic scission of O2 and formation of compound I, i.e. Por+-Fe(IV)=O, and water. The function of the acid-alcohol pair appears to be replaced by a different amide residue, Asn938 of 7,8-LDS, for heterolysis of (8R,9Z,12Z)-8-hydroperoxyoctadeca-9,12-dienoate to generate compound I
724132
Gaeumannomyces graminis
?
-
-
-
-
additional information
the bifunctional enzyme forms 5S,8S-dihydroxylinoleic acid from (8R)-hydroperoxylinoleic acid by intramolecular oxygen transfer. Linoleate diol synthases are fungal dioxygenase-cytochrome P450 fusion enzymes. P450 hydroxylases usually contain an acid-alcohol pair in the I-helices for the heterolytic scission of O2 and formation of compound I, i.e. Por+-Fe(IV)=O, and water. The function of the acid-alcohol pair appears to be replaced by a different amide residue, Gln890 of 5,8-LDS, for heterolysis of (8R,9Z,12Z)-8-hydroperoxyoctadeca-9,12-dienoate to generate compound I
724132
Aspergillus fumigatus
?
-
-
-
-
additional information
the enzyme forms (5S,8R)-5,8-dihydroxylinoleic acid from (8R)-hydroperoxylinoleic acid by intramolecular oxygen transfer. Linoleate diol synthases are fungal dioxygenase-cytochrome P450 fusion enzymes
724132
Aspergillus fumigatus
?
-
-
-
-
Subunits (protein specific)
Subunits
Commentary
Organism
More
homology model of 5,8-LDS, overview
Aspergillus fumigatus
More
homology model of 7,8-LDS, overview
Gaeumannomyces graminis
General Information
General Information
Commentary
Organism
additional information
homology model of 5,8-LDS, overview
Aspergillus fumigatus
additional information
homology model of 7,8-LDS, overview
Gaeumannomyces graminis
General Information (protein specific)
General Information
Commentary
Organism
additional information
homology model of 5,8-LDS, overview
Aspergillus fumigatus
additional information
homology model of 7,8-LDS, overview
Gaeumannomyces graminis
Other publictions for EC
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)
741712
Seo
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Colletotrichum gloeosporioides, Colletotrichum gloeosporioides KACC 40961
Appl. Microbiol. Biotechnol.
100
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2016
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-
1
-
11
-
-
17
-
-
1
1
1
5
-
-
1
-
-
1
8
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25
3
1
2
-
1
18
3
-
-
-
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1
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1
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11
-
-
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17
-
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1
1
1
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1
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1
8
-
25
3
2
-
1
18
3
-
-
-
-
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-
20
20
742730
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J. Agric. Food Chem.
64
8555-8562
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1
1
1
-
1
-
-
-
-
-
-
2
-
6
-
-
1
-
-
1
-
-
14
-
3
1
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-
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1
-
-
-
-
-
-
1
1
1
-
-
1
-
-
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-
-
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2
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1
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1
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14
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1
-
-
-
1
-
-
-
-
-
-
-
-
-
743200
Sooman
Discovery of a novel linoleat ...
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50
1243-1252
2015
-
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1
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5
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13
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29
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5
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29
-
2
2
-
-
-
-
-
-
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2
2
-
-
-
724132
Hoffmann
7,8- and 5,8-linoleate diol sy ...
Aspergillus fumigatus, Gaeumannomyces graminis
Arch. Biochem. Biophys.
539
87-91
2013
-
-
2
-
7
-
-
-
-
-
-
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4
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5
2
4
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2
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7
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5
2
-
-
-
-
-
-
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2
2
-
-
-
711024
Hoffmann
Expression of 5,8-LDS of Asper ...
Aspergillus fumigatus, Gaeumannomyces graminis
Arch. Biochem. Biophys.
506
216-222
2010
-
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2
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6
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2
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3
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4
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2
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10
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2
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7
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3
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2
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10
-
-
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-
-
-
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2
2
-
-
-
714317
Jernerén
Reaction mechanism of 5,8-lino ...
Aspergillus clavatus
Biochim. Biophys. Acta
1801
503-507
2010
-
-
-
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1
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4
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2
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704466
Brodhun
Identification of PpoA from As ...
Aspergillus nidulans
J. Biol. Chem.
284
11792-11805
2009
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1
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2
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1
4
-
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2
1
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1
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1
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7
1
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1
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1
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1
2
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2
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1
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4
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1
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1
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1
-
7
1
1
-
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4
1
-
-
-
-
-
-
-
4
4
704475
Garscha
Leucine/valine residues direct ...
Gaeumannomyces graminis
J. Biol. Chem.
284
13755-13765
2009
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-
1
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4
-
-
-
-
-
-
1
-
2
-
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2
-
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-
-
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-
-
-
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702018
Garscha
Pichia expression and mutagene ...
Gaeumannomyces graminis, Gaeumannomyces graminis var. avenae
Biochem. Biophys. Res. Commun.
373
579-583
2008
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1
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3
-
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2
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4
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1
1
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1
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4
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703700
Garscha
Critical amino acids for the 8 ...
Gaeumannomyces graminis
FEBS Lett.
582
3547-3551
2008
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1
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11
-
-
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-
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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
1
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11
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1
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-
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-
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-
-
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285246
Hörnsten
Cloning of linoleate diol synt ...
Gaeumannomyces graminis
J. Biol. Chem.
274
28219-28224
1999
-
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1
-
-
-
-
-
-
1
1
-
-
2
-
-
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-
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1
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1
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-
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-
-
-
-
-
-
-
-
-
-
285251
Oliw
Catalytic properties of linole ...
Gaeumannomyces graminis
Adv. Exp. Med. Biol.
469
679-685
1999
2
-
-
-
-
-
2
-
-
-
1
1
-
2
-
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1
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1
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1
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1
1
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-
-
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-
-
-
285244
Su
A protein radical and ferryl i ...
Gaeumannomyces graminis
J. Biol. Chem.
273
20744-20751
1998
-
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-
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1
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-
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2
-
4
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5
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-
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285243
Su
Purification and characterizat ...
Gaeumannomyces graminis
J. Biol. Chem.
271
14112-14118
1996
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2
2
2
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2
1
1
1
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1
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1
1
1
2
1
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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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2
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2
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2
-
-
2
1
1
-
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1
-
1
1
1
2
1
-
-
-
1
1
-
-
1
-
-
-
-
-
-
285249
Su
Studies on linoleic acid 8R-di ...
Gaeumannomyces graminis
Lipids
30
43-50
1995
-
-
-
-
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1
16
-
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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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1
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1
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1
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16
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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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-
-
-
-
285247
Brodowsky
BW A4C and other hydroxamic ac ...
Gaeumannomyces graminis
Eur. J. Pharmacol.
254
43-47
1994
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12
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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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6
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6
12
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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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285248
Brodowsky
Linoleic acid 8R-dioxygenase a ...
Gaeumannomyces graminis
Ann. N. Y. Acad. Sci.
744
314-316
1994
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5
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285250
Hamberg
Sequential oxygenation of lino ...
Gaeumannomyces graminis
Arch. Biochem. Biophys.
309
77-80
1994
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4
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285245
Brodowsky
A linoleic acid (8R)-dioxygena ...
Gaeumannomyces graminis
J. Biol. Chem.
267
14738-14745
1992
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