BRENDA - Enzyme Database show
show all sequences of 1.1.1.252

Towards the first inhibitors of trihydroxynaphthalene reductase from Curvularia lunata: Synthesis of artificial substrate, homology modelling and initial screening

Brunskole, M.; Stefane, B.; Zorko, K.; Anderluh, M.; Stojan, J.; Lanisnik Rizner, T.; Gobec, S.; Bioorg. Med. Chem. 16, 5881-5889 (2008)

Data extracted from this reference:

Application
Application
Commentary
Organism
drug development
the enzyme represents a target for the development of fungicides and antimicotics
Curvularia lunata
Cloned(Commentary)
Commentary
Organism
GST-tagged enzyme expression in Escherichia coli
Curvularia lunata
Inhibitors
Inhibitors
Commentary
Organism
Structure
1H-indene-1,3(2H)-dione
-
Curvularia lunata
2,3-Dihydro-2,5-dihydroxy-4H-benzopyran-4-one
DDBO, an artificial substrate, chemical synthesis method development, overview
Curvularia lunata
diclofenac
-
Curvularia lunata
ethyl 6-methyl-4-oxo-4H-chromene-2-carboxylate
-
Curvularia lunata
ethyl 6-methyl-8-nitro-4-oxo-4H-chromene-2-carboxylate
-
Curvularia lunata
etodolac
-
Curvularia lunata
nabumetone
-
Curvularia lunata
Natural Substrates/ Products (Substrates)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
1,3,8-trihydroxynaphthalene + NADPH + H+
Curvularia lunata
the enzyme is an essential enzyme in the biosynthesis of fungal melanin
vermelone + NADP+
-
-
?
Organism
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
Curvularia lunata
-
-
-
Purification (Commentary)
Commentary
Organism
recombinant GST-tagged enzyme from Escherichia coli by glutathione affinity chromatography
Curvularia lunata
Reaction
Reaction
Commentary
Organism
scytalone + NADP+ = 1,3,6,8-tetrahydroxynaphthalene + NADPH + H+
the catalytic triad is formed by residues S149, Y163, and K167
Curvularia lunata
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
1,3,8-trihydroxynaphthalene + NADPH + H+
-
685550
Curvularia lunata
vermelone + NADP+
-
-
-
?
1,3,8-trihydroxynaphthalene + NADPH + H+
the enzyme is an essential enzyme in the biosynthesis of fungal melanin
685550
Curvularia lunata
vermelone + NADP+
-
-
-
?
Subunits
Subunits
Commentary
Organism
More
enzyme homology modelling, overview
Curvularia lunata
pH Optimum
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
7
-
assay at
Curvularia lunata
Cofactor
Cofactor
Commentary
Organism
Structure
NADPH
-
Curvularia lunata
Ki Value [mM]
Ki Value [mM]
Ki Value maximum [mM]
Inhibitor
Commentary
Organism
Structure
0.017
-
1H-indene-1,3(2H)-dione
pH 7.0
Curvularia lunata
0.017
-
etodolac
pH 7.0
Curvularia lunata
0.108
-
diclofenac
pH 7.0
Curvularia lunata
0.108
-
ethyl 6-methyl-4-oxo-4H-chromene-2-carboxylate
pH 7.0
Curvularia lunata
0.111
-
ethyl 6-methyl-8-nitro-4-oxo-4H-chromene-2-carboxylate
pH 7.0
Curvularia lunata
0.111
-
nabumetone
pH 7.0
Curvularia lunata
Application (protein specific)
Application
Commentary
Organism
drug development
the enzyme represents a target for the development of fungicides and antimicotics
Curvularia lunata
Cloned(Commentary) (protein specific)
Commentary
Organism
GST-tagged enzyme expression in Escherichia coli
Curvularia lunata
Cofactor (protein specific)
Cofactor
Commentary
Organism
Structure
NADPH
-
Curvularia lunata
Inhibitors (protein specific)
Inhibitors
Commentary
Organism
Structure
1H-indene-1,3(2H)-dione
-
Curvularia lunata
2,3-Dihydro-2,5-dihydroxy-4H-benzopyran-4-one
DDBO, an artificial substrate, chemical synthesis method development, overview
Curvularia lunata
diclofenac
-
Curvularia lunata
ethyl 6-methyl-4-oxo-4H-chromene-2-carboxylate
-
Curvularia lunata
ethyl 6-methyl-8-nitro-4-oxo-4H-chromene-2-carboxylate
-
Curvularia lunata
etodolac
-
Curvularia lunata
nabumetone
-
Curvularia lunata
Ki Value [mM] (protein specific)
Ki Value [mM]
Ki Value maximum [mM]
Inhibitor
Commentary
Organism
Structure
0.017
-
1H-indene-1,3(2H)-dione
pH 7.0
Curvularia lunata
0.017
-
etodolac
pH 7.0
Curvularia lunata
0.108
-
diclofenac
pH 7.0
Curvularia lunata
0.108
-
ethyl 6-methyl-4-oxo-4H-chromene-2-carboxylate
pH 7.0
Curvularia lunata
0.111
-
ethyl 6-methyl-8-nitro-4-oxo-4H-chromene-2-carboxylate
pH 7.0
Curvularia lunata
0.111
-
nabumetone
pH 7.0
Curvularia lunata
Natural Substrates/ Products (Substrates) (protein specific)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
1,3,8-trihydroxynaphthalene + NADPH + H+
Curvularia lunata
the enzyme is an essential enzyme in the biosynthesis of fungal melanin
vermelone + NADP+
-
-
?
Purification (Commentary) (protein specific)
Commentary
Organism
recombinant GST-tagged enzyme from Escherichia coli by glutathione affinity chromatography
Curvularia lunata
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
1,3,8-trihydroxynaphthalene + NADPH + H+
-
685550
Curvularia lunata
vermelone + NADP+
-
-
-
?
1,3,8-trihydroxynaphthalene + NADPH + H+
the enzyme is an essential enzyme in the biosynthesis of fungal melanin
685550
Curvularia lunata
vermelone + NADP+
-
-
-
?
Subunits (protein specific)
Subunits
Commentary
Organism
More
enzyme homology modelling, overview
Curvularia lunata
pH Optimum (protein specific)
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
7
-
assay at
Curvularia lunata
Other publictions for EC 1.1.1.252
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)
723949
Schaetzle
Tetrahydroxynaphthalene reduct ...
Magnaporthe grisea
Angew. Chem. Int. Ed. Engl.
51
2643-2646
2012
-
-
-
-
1
-
-
-
-
-
-
1
-
2
-
-
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14
-
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1
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1
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1
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1
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14
-
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-
-
-
-
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-
3
3
-
-
-
697274
Brunskole
Trihydroxynaphthalene reductas ...
Curvularia lunata
Chem. Biol. Interact.
178
259-267
2009
-
1
1
-
-
-
27
1
-
-
-
-
-
7
-
-
1
-
-
-
1
-
1
-
-
-
-
-
-
-
-
1
14
-
14
-
1
1
1
-
-
-
14
27
14
1
-
-
-
-
-
-
-
1
-
-
1
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
697275
Stojan
Simultaneous binding of coenzy ...
Curvularia lunata
Chem. Biol. Interact.
178
268-273
2009
-
-
1
-
-
-
2
-
-
-
-
-
-
2
-
-
1
-
-
-
-
-
1
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-
-
-
-
-
-
-
1
-
-
-
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-
1
1
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2
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1
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-
1
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-
-
-
-
-
-
-
-
-
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-
697279
Kristan
Two homologous fungal carbonyl ...
Curvularia lunata
Chem. Biol. Interact.
178
295-302
2009
-
-
1
-
-
-
11
-
-
-
-
1
-
4
-
-
1
-
-
-
-
-
12
-
1
-
-
-
1
-
-
-
-
-
10
-
-
1
-
-
-
-
10
11
-
-
-
-
-
1
-
-
-
1
-
-
-
-
12
-
1
-
-
-
1
-
-
-
-
-
-
-
-
-
713194
Zhang
-
Resistance development in rice ...
Magnaporthe grisea
Pestic. Biochem. Physiol.
94
43-47
2009
-
1
-
-
-
-
1
-
-
-
-
-
-
1
-
-
-
-
-
-
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-
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1
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1
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-
-
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-
-
-
-
-
-
-
-
-
685550
Brunskole
Towards the first inhibitors o ...
Curvularia lunata
Bioorg. Med. Chem.
16
5881-5889
2008
-
1
1
-
-
-
7
-
-
-
-
1
-
4
-
-
1
1
-
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2
1
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1
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1
6
-
-
-
1
1
1
-
-
-
-
7
6
-
-
-
-
1
-
-
-
1
-
-
-
-
2
1
-
-
-
-
1
-
-
-
-
-
-
-
-
-
688618
Rostkowski
Analysis of conformer stabilit ...
Fungi
J. Phys. Chem. B
111
8314-8320
2007
-
-
-
-
-
-
-
-
-
-
-
2
-
1
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4
1
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1
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1
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2
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4
1
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656846
Tsuji
Evidence for involvement of tw ...
Colletotrichum lagenaria
Mycol. Res.
107
854-860
2003
-
-
1
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-
-
-
-
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1
-
1
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3
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1
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1
1
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1
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3
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9577
Thompson
2,3-Dihydro-2,5-dihydroxy-4H-b ...
Magnaporthe grisea
Anal. Biochem.
256
1-6
1998
-
-
-
-
-
-
-
1
-
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-
1
-
1
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4
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1
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1
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1
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4
-
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1
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-
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9571
Thompson
Trihydroxynaphthalene reductas ...
Magnaporthe grisea
Biochemistry
36
1852-1860
1997
-
-
-
-
-
-
1
6
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1
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3
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6
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3
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3
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3
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1
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6
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1
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6
-
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3
-
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-
9578
Andersson
A flexible lid controls access ...
Magnaporthe grisea
FEBS Lett.
400
173-176
1997
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-
1
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3
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1
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9572
Andersson
Crystallization and preliminar ...
Magnaporthe grisea
Proteins Struct. Funct. Genet.
24
525-527
1996
-
-
-
1
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1
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2
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1
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2
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2
1
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1
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1
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9573
Perpetua
Cloning and characterization o ...
Colletotrichum lagenaria
Mol. Plant Microbe Interact.
9
323-329
1996
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-
1
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1
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7
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2
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1
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1
1
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1
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2
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9576
Andersson
Crystal structure of the terna ...
Magnaporthe grisea
Structure
4
1161-1170
1996
-
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1
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1
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1
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4
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3
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1
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1
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3
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9570
Vidal-Cros
Polyhydroxynaphthalene reducta ...
Magnaporthe grisea
Eur. J. Biochem.
219
985-992
1994
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-
1
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3
1
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4
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1
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1
1
3
1
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1
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1
1
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3
1
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1
1
3
1
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9574
Ichinose
Post-aromatic deoxygenation in ...
Phialocephala lagerbergii
Chem. Pharm. Bull.
41
2015-2021
1993
-
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1
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3
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3
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9575
Viviani
-
Deoxygenation of polyphenols b ...
Magnaporthe oryzae
Bull. Soc. Chim. Fr.
130
395-404
1993
-
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2
3
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1
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3
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2
2
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2
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2
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2
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3
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3
-
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2
2
-
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-
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-
9569
Wheeler
-
The inhibition of melanin bios ...
Magnaporthe oryzae
Exp. Mycol.
12
151-160
1988
-
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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1
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8
-
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1
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3
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