BRENDA - Enzyme Database show
show all sequences of 1.1.1.252

Tetrahydroxynaphthalene reductase: catalytic properties of an enzyme involved in reductive asymmetric naphthol dearomatization

Schaetzle, M.A.; Flemming, S.; Husain, S.M.; Richter, M.; Guenther, S.; Mueller, M.; Angew. Chem. Int. Ed. Engl. 51, 2643-2646 (2012)

Data extracted from this reference:

Engineering
Amino acid exchange
Commentary
Organism
additional information
generation of the C-terminally Ile274-truncated variant T4HNR(1-273)
Magnaporthe grisea
Natural Substrates/ Products (Substrates)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
1,3,6,8-tetrahydroxynaphthalene + NADPH + H+
Magnaporthe grisea
reduction reaction via the via the 3-keto tautomer of 1,3,6,8-tetrahydroxynaphthalene
scytalone + NADP+
-
-
?
Organism
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
Magnaporthe grisea
-
-
-
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
1,3,6,8-tetrahydroxynaphthalene + NADPH + H+
reduction reaction via the via the 3-keto tautomer of 1,3,6,8-tetrahydroxynaphthalene
723949
Magnaporthe grisea
scytalone + NADP+
-
-
-
?
1,3,6,8-tetrahydroxynaphthalene + NADPH + H+
with enatiomeric excess of over 95%, reduction reaction via the via the 3-oxo tautomer of 1,3,6,8-tetrahydroxynaphthalene
723949
Magnaporthe grisea
scytalone + NADP+
-
-
-
?
1,3,6-trihydroxynaphthalene + NADPH + H+
-
723949
Magnaporthe grisea
(R)-8-deoxyscytalone + NADP+
-
-
-
?
1,3-dihydroxynaphthalene + NADPH + H+
very low activity
723949
Magnaporthe grisea
3-hydroxy-3,4-dihydronaphthalen-1(2H)-one + NADP+
-
-
-
?
2-methylcyclohexanone + NADPH + H+
-
723949
Magnaporthe grisea
trans-2-methylcyclohexanol + NADP+
-
-
-
?
2-tetralone + NADPH + H+
high activity, almost complete conversion
723949
Magnaporthe grisea
2-tetralol + NADP+
-
-
-
?
5-hydroxy-2-tetralone + NADPH + H+
-
723949
Magnaporthe grisea
5-hydroxy-2-tetralol + NADP+
-
-
-
?
5-methoxy-2-tetralone + NADPH + H+
high activity, almost complete conversion
723949
Magnaporthe grisea
5-methoxy-2-tetralol + NADP+
-
-
-
?
6-hydroxy-2-tetralone + NADPH + H+
-
723949
Magnaporthe grisea
6-hydroxy-2-tetralol + NADP+
-
-
-
?
6-methoxy-2-tetralone + NADPH + H+
-
723949
Magnaporthe grisea
6-methoxy-2-tetralol + NADP+
-
-
-
?
7-hydroxy-2-tetralone + NADPH + H+
high activity, almost complete conversion
723949
Magnaporthe grisea
7-hydroxy-2-tetralol + NADP+
-
-
-
?
7-methoxy-2-tetralone + NADPH + H+
high activity, almost complete conversion
723949
Magnaporthe grisea
7-methoxy-2-tetralol + NADP+
-
-
-
?
8-hydroxy-2-tetralone + NADPH + H+
high activity, almost complete conversion
723949
Magnaporthe grisea
8-hydroxy-2-tetralol + NADP+
-
-
-
?
8-methoxy-2-tetralone + NADPH + H+
high activity, almost complete conversion
723949
Magnaporthe grisea
8-methoxy-2-tetralol + NADP+
-
-
-
?
Cofactor
Cofactor
Commentary
Organism
Structure
NADPH
-
Magnaporthe grisea
Cofactor (protein specific)
Cofactor
Commentary
Organism
Structure
NADPH
-
Magnaporthe grisea
Engineering (protein specific)
Amino acid exchange
Commentary
Organism
additional information
generation of the C-terminally Ile274-truncated variant T4HNR(1-273)
Magnaporthe grisea
Natural Substrates/ Products (Substrates) (protein specific)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
1,3,6,8-tetrahydroxynaphthalene + NADPH + H+
Magnaporthe grisea
reduction reaction via the via the 3-keto tautomer of 1,3,6,8-tetrahydroxynaphthalene
scytalone + NADP+
-
-
?
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
1,3,6,8-tetrahydroxynaphthalene + NADPH + H+
reduction reaction via the via the 3-keto tautomer of 1,3,6,8-tetrahydroxynaphthalene
723949
Magnaporthe grisea
scytalone + NADP+
-
-
-
?
1,3,6,8-tetrahydroxynaphthalene + NADPH + H+
with enatiomeric excess of over 95%, reduction reaction via the via the 3-oxo tautomer of 1,3,6,8-tetrahydroxynaphthalene
723949
Magnaporthe grisea
scytalone + NADP+
-
-
-
?
1,3,6-trihydroxynaphthalene + NADPH + H+
-
723949
Magnaporthe grisea
(R)-8-deoxyscytalone + NADP+
-
-
-
?
1,3-dihydroxynaphthalene + NADPH + H+
very low activity
723949
Magnaporthe grisea
3-hydroxy-3,4-dihydronaphthalen-1(2H)-one + NADP+
-
-
-
?
2-methylcyclohexanone + NADPH + H+
-
723949
Magnaporthe grisea
trans-2-methylcyclohexanol + NADP+
-
-
-
?
2-tetralone + NADPH + H+
high activity, almost complete conversion
723949
Magnaporthe grisea
2-tetralol + NADP+
-
-
-
?
5-hydroxy-2-tetralone + NADPH + H+
-
723949
Magnaporthe grisea
5-hydroxy-2-tetralol + NADP+
-
-
-
?
5-methoxy-2-tetralone + NADPH + H+
high activity, almost complete conversion
723949
Magnaporthe grisea
5-methoxy-2-tetralol + NADP+
-
-
-
?
6-hydroxy-2-tetralone + NADPH + H+
-
723949
Magnaporthe grisea
6-hydroxy-2-tetralol + NADP+
-
-
-
?
6-methoxy-2-tetralone + NADPH + H+
-
723949
Magnaporthe grisea
6-methoxy-2-tetralol + NADP+
-
-
-
?
7-hydroxy-2-tetralone + NADPH + H+
high activity, almost complete conversion
723949
Magnaporthe grisea
7-hydroxy-2-tetralol + NADP+
-
-
-
?
7-methoxy-2-tetralone + NADPH + H+
high activity, almost complete conversion
723949
Magnaporthe grisea
7-methoxy-2-tetralol + NADP+
-
-
-
?
8-hydroxy-2-tetralone + NADPH + H+
high activity, almost complete conversion
723949
Magnaporthe grisea
8-hydroxy-2-tetralol + NADP+
-
-
-
?
8-methoxy-2-tetralone + NADPH + H+
high activity, almost complete conversion
723949
Magnaporthe grisea
8-methoxy-2-tetralol + NADP+
-
-
-
?
General Information
General Information
Commentary
Organism
evolution
the enzyme is a member of the short-chain dehydrogenase/reductase (SDR) family of enzymes
Magnaporthe grisea
metabolism
the enzyme catalyzes a step in 1,8-dihydroxynaphthalene-melanin biosynthesis, overview
Magnaporthe grisea
additional information
structure-activity relationship of T4HNR and dynamics of its catalytic cycle, substrate docking study, the carboxylate of Ile274 might have an impact on substrate orientation, overview. Two orientations of tetralones in the active site of T4HNR revealed by docking studies: 1. si-face orientation (representing the preferential hydrophobic interaction of the methoxy group of substrate 5-methoxy-2-tetralone) and 2. the re-face orientation
Magnaporthe grisea
General Information (protein specific)
General Information
Commentary
Organism
evolution
the enzyme is a member of the short-chain dehydrogenase/reductase (SDR) family of enzymes
Magnaporthe grisea
metabolism
the enzyme catalyzes a step in 1,8-dihydroxynaphthalene-melanin biosynthesis, overview
Magnaporthe grisea
additional information
structure-activity relationship of T4HNR and dynamics of its catalytic cycle, substrate docking study, the carboxylate of Ile274 might have an impact on substrate orientation, overview. Two orientations of tetralones in the active site of T4HNR revealed by docking studies: 1. si-face orientation (representing the preferential hydrophobic interaction of the methoxy group of substrate 5-methoxy-2-tetralone) and 2. the re-face orientation
Magnaporthe grisea
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
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1
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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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3
3
-
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697274
Brunskole
Trihydroxynaphthalene reductas ...
Curvularia lunata
Chem. Biol. Interact.
178
259-267
2009
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1
1
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27
1
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7
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1
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1
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1
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1
14
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14
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1
1
1
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14
27
14
1
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1
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1
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1
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697275
Stojan
Simultaneous binding of coenzy ...
Curvularia lunata
Chem. Biol. Interact.
178
268-273
2009
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1
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697279
Kristan
Two homologous fungal carbonyl ...
Curvularia lunata
Chem. Biol. Interact.
178
295-302
2009
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1
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11
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1
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4
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1
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12
-
1
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1
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10
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1
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10
11
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1
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1
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12
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1
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1
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713194
Zhang
-
Resistance development in rice ...
Magnaporthe grisea
Pestic. Biochem. Physiol.
94
43-47
2009
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1
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1
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1
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685550
Brunskole
Towards the first inhibitors o ...
Curvularia lunata
Bioorg. Med. Chem.
16
5881-5889
2008
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1
1
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7
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1
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4
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1
1
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2
1
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1
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1
6
-
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1
1
1
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7
6
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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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688618
Rostkowski
Analysis of conformer stabilit ...
Fungi
J. Phys. Chem. B
111
8314-8320
2007
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2
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1
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1
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656846
Tsuji
Evidence for involvement of tw ...
Colletotrichum lagenaria
Mycol. Res.
107
854-860
2003
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9577
Thompson
2,3-Dihydro-2,5-dihydroxy-4H-b ...
Magnaporthe grisea
Anal. Biochem.
256
1-6
1998
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4
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1
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9571
Thompson
Trihydroxynaphthalene reductas ...
Magnaporthe grisea
Biochemistry
36
1852-1860
1997
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1
6
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6
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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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9572
Andersson
Crystallization and preliminar ...
Magnaporthe grisea
Proteins Struct. Funct. Genet.
24
525-527
1996
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9573
Perpetua
Cloning and characterization o ...
Colletotrichum lagenaria
Mol. Plant Microbe Interact.
9
323-329
1996
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7
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9576
Andersson
Crystal structure of the terna ...
Magnaporthe grisea
Structure
4
1161-1170
1996
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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
3
1
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1
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1
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1
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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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9575
Viviani
-
Deoxygenation of polyphenols b ...
Magnaporthe oryzae
Bull. Soc. Chim. Fr.
130
395-404
1993
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9569
Wheeler
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The inhibition of melanin bios ...
Magnaporthe oryzae
Exp. Mycol.
12
151-160
1988
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