BRENDA - Enzyme Database show
show all sequences of 1.1.1.B57

Unprecedented role of hydronaphthoquinone tautomers in biosynthesis

Husain, S.; Schaetzle, M.; Luedeke, S.; Mueller, M.; Angew. Chem. Int. Ed. Engl. 53, 9806-9811 (2014)

Data extracted from this reference:

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
-
(R)-scytalone + NADP+
-
-
?
1,3,6,8-tetrahydroxynaphthalene + NADPH + H+
Magnaporthe grisea ATCC MYA-4617
-
(R)-scytalone + NADP+
-
-
?
1,3,8-trihydroxynaphthalene + NADPH + H+
Magnaporthe grisea
-
(R)-vermelone + NADP+
-
-
?
1,3,8-trihydroxynaphthalene + NADPH + H+
Magnaporthe grisea ATCC MYA-4617
-
(R)-vermelone + NADP+
-
-
?
Organism
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
Magnaporthe grisea
Q12634
-
-
Magnaporthe grisea ATCC MYA-4617
Q12634
-
-
Reaction
Reaction
Commentary
Organism
1-tetralone + NADPH + H+ = 1-tetralol + NADP+
reaction mechanism, overview
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+
-
741603
Magnaporthe grisea
(R)-scytalone + NADP+
-
-
-
?
1,3,6,8-tetrahydroxynaphthalene + NADPH + H+
-
741603
Magnaporthe grisea ATCC MYA-4617
(R)-scytalone + NADP+
-
-
-
?
1,3,8-trihydroxynaphthalene + NADPH + H+
-
741603
Magnaporthe grisea
(R)-vermelone + NADP+
-
-
-
?
1,3,8-trihydroxynaphthalene + NADPH + H+
-
741603
Magnaporthe grisea ATCC MYA-4617
(R)-vermelone + NADP+
-
-
-
?
2,3-dihydronaphthalene-1,4-dione + NADPH + H+
-
741603
Magnaporthe grisea
(S)-4-hydroxy-1-tetralone + NADP+
-
-
-
?
2,3-dihydronaphthalene-1,4-dione + NADPH + H+
-
741603
Magnaporthe grisea ATCC MYA-4617
(S)-4-hydroxy-1-tetralone + NADP+
-
-
-
?
2,3-epoxy-1,4-naphthoquinone + NADPH + H+
-
741603
Magnaporthe grisea
(1aS,7R,7aS)-7-hydroxy-7,7a-dihydronaphtho[2,3-b]oxiren-2(1aH)-one + NADP+
-
-
-
?
2,3-epoxy-1,4-naphthoquinone + NADPH + H+
-
741603
Magnaporthe grisea ATCC MYA-4617
(1aS,7R,7aS)-7-hydroxy-7,7a-dihydronaphtho[2,3-b]oxiren-2(1aH)-one + NADP+
-
-
-
?
2-hydroxy-1,4-naphthoquinone + 2 NADPH + H+
i.e. lawsone, enzyme T4HNR exhibits high diastereoselectivity (cis/trans99:1), high enantiomeric excess (over 99% ee), and 90% yield. The putative two-step enzymatic formation of cis-ketodiol from 2-hydroxyquinone lawsone does not involve the hydroquinone. Stable 1,4-diketo tautomer intermediate
741603
Magnaporthe grisea
(3S,4R)-3,4-dihydroxy-1-tetralone + 2 NADP+
-
-
-
?
2-hydroxy-1,4-naphthoquinone + NADPH + H+
-
741603
Magnaporthe grisea
cis-3,4-dihydroxy-1-tetralone + NADP+
-
-
-
?
5-hydroxy-2,3-dihydronaphthalene-1,4-dione + NADPH + H+
-
741603
Magnaporthe grisea
(S)-4,8-dihydroxy-1-tetralone + NADP+
-
-
-
?
flaviolin + NADPH + H+
-
741603
Magnaporthe grisea
cis-(3S,4R)-4-hydroxyscytalone + NADP+
-
-
-
?
additional information
NADPH-dependent enzymatic reduction of 2-hydroxynaphthoquinones, resulting in 3,4-dihydroxy-1-tetralones, proceeds via the stable 1,4-diketo tautomer of the hydronaphthoquinones. No activity with 1,2,4-trihydroxynaphthalene. Hydronaphthoquinone tautomers play an unprecedented and essential role in the biosynthesis of many natural products and are involved in breaking the redox cycle of quinones-hydroquinones. Menadione epoxide is a poor substrate
741603
Magnaporthe grisea
?
-
-
-
-
additional information
NADPH-dependent enzymatic reduction of 2-hydroxynaphthoquinones, resulting in 3,4-dihydroxy-1-tetralones, proceeds via the stable 1,4-diketo tautomer of the hydronaphthoquinones. No activity with 1,2,4-trihydroxynaphthalene. Hydronaphthoquinone tautomers play an unprecedented and essential role in the biosynthesis of many natural products and are involved in breaking the redox cycle of quinones-hydroquinones. Menadione epoxide is a poor substrate
741603
Magnaporthe grisea ATCC MYA-4617
?
-
-
-
-
Cofactor
Cofactor
Commentary
Organism
Structure
NADPH
-
Magnaporthe grisea
Cofactor (protein specific)
Cofactor
Commentary
Organism
Structure
NADPH
-
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
-
(R)-scytalone + NADP+
-
-
?
1,3,6,8-tetrahydroxynaphthalene + NADPH + H+
Magnaporthe grisea ATCC MYA-4617
-
(R)-scytalone + NADP+
-
-
?
1,3,8-trihydroxynaphthalene + NADPH + H+
Magnaporthe grisea
-
(R)-vermelone + NADP+
-
-
?
1,3,8-trihydroxynaphthalene + NADPH + H+
Magnaporthe grisea ATCC MYA-4617
-
(R)-vermelone + 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+
-
741603
Magnaporthe grisea
(R)-scytalone + NADP+
-
-
-
?
1,3,6,8-tetrahydroxynaphthalene + NADPH + H+
-
741603
Magnaporthe grisea ATCC MYA-4617
(R)-scytalone + NADP+
-
-
-
?
1,3,8-trihydroxynaphthalene + NADPH + H+
-
741603
Magnaporthe grisea
(R)-vermelone + NADP+
-
-
-
?
1,3,8-trihydroxynaphthalene + NADPH + H+
-
741603
Magnaporthe grisea ATCC MYA-4617
(R)-vermelone + NADP+
-
-
-
?
2,3-dihydronaphthalene-1,4-dione + NADPH + H+
-
741603
Magnaporthe grisea
(S)-4-hydroxy-1-tetralone + NADP+
-
-
-
?
2,3-dihydronaphthalene-1,4-dione + NADPH + H+
-
741603
Magnaporthe grisea ATCC MYA-4617
(S)-4-hydroxy-1-tetralone + NADP+
-
-
-
?
2,3-epoxy-1,4-naphthoquinone + NADPH + H+
-
741603
Magnaporthe grisea
(1aS,7R,7aS)-7-hydroxy-7,7a-dihydronaphtho[2,3-b]oxiren-2(1aH)-one + NADP+
-
-
-
?
2,3-epoxy-1,4-naphthoquinone + NADPH + H+
-
741603
Magnaporthe grisea ATCC MYA-4617
(1aS,7R,7aS)-7-hydroxy-7,7a-dihydronaphtho[2,3-b]oxiren-2(1aH)-one + NADP+
-
-
-
?
2-hydroxy-1,4-naphthoquinone + 2 NADPH + H+
i.e. lawsone, enzyme T4HNR exhibits high diastereoselectivity (cis/trans99:1), high enantiomeric excess (over 99% ee), and 90% yield. The putative two-step enzymatic formation of cis-ketodiol from 2-hydroxyquinone lawsone does not involve the hydroquinone. Stable 1,4-diketo tautomer intermediate
741603
Magnaporthe grisea
(3S,4R)-3,4-dihydroxy-1-tetralone + 2 NADP+
-
-
-
?
2-hydroxy-1,4-naphthoquinone + NADPH + H+
-
741603
Magnaporthe grisea
cis-3,4-dihydroxy-1-tetralone + NADP+
-
-
-
?
5-hydroxy-2,3-dihydronaphthalene-1,4-dione + NADPH + H+
-
741603
Magnaporthe grisea
(S)-4,8-dihydroxy-1-tetralone + NADP+
-
-
-
?
flaviolin + NADPH + H+
-
741603
Magnaporthe grisea
cis-(3S,4R)-4-hydroxyscytalone + NADP+
-
-
-
?
additional information
NADPH-dependent enzymatic reduction of 2-hydroxynaphthoquinones, resulting in 3,4-dihydroxy-1-tetralones, proceeds via the stable 1,4-diketo tautomer of the hydronaphthoquinones. No activity with 1,2,4-trihydroxynaphthalene. Hydronaphthoquinone tautomers play an unprecedented and essential role in the biosynthesis of many natural products and are involved in breaking the redox cycle of quinones-hydroquinones. Menadione epoxide is a poor substrate
741603
Magnaporthe grisea
?
-
-
-
-
additional information
NADPH-dependent enzymatic reduction of 2-hydroxynaphthoquinones, resulting in 3,4-dihydroxy-1-tetralones, proceeds via the stable 1,4-diketo tautomer of the hydronaphthoquinones. No activity with 1,2,4-trihydroxynaphthalene. Hydronaphthoquinone tautomers play an unprecedented and essential role in the biosynthesis of many natural products and are involved in breaking the redox cycle of quinones-hydroquinones. Menadione epoxide is a poor substrate
741603
Magnaporthe grisea ATCC MYA-4617
?
-
-
-
-
General Information
General Information
Commentary
Organism
evolution
enzyme T4HNR is a member of the short-chain dehydrogenases/ reductases (SDR) enzyme family
Magnaporthe grisea
metabolism
the enzyme plays an integral part in the biosynthesis of 1,8-dihydroxynaphthalene (DHN) melanin, a virulence factor of many filamentous fungi, together with scytalone dehydratase, pathway overview. DHN melanin biosynthesis constitutes a diversity-oriented metabolic network, comprising vicinal ketodiol and 4-hydroxy-1-tetralone biosyntheses as branching points. Polyhydroxynaphthalene reductases are involved in promiscuous reduction reactions, reflecting the idea of a matrix biosynthetic pathway, involvement of polyhydroxynaphthalene reductases in spirodioxynaphthalene biosynthesis
Magnaporthe grisea
physiological function
the enzyme plays an integral part in the biosynthesis of 1,8-dihydroxynaphthalene (DHN) melanin, a virulence factor of many filamentous fungi, togeher with scytalone dehydratase, pathway overview. Hundreds of metabolites, such as the dalmanols, balticols, 3,4-dihydroxy-1-tetralones, 4-hydroxy-1-tetralones, and spirodioxynaphthalenes are derived from the intermediate polyhydroxynaphthalenes
Magnaporthe grisea
General Information (protein specific)
General Information
Commentary
Organism
evolution
enzyme T4HNR is a member of the short-chain dehydrogenases/ reductases (SDR) enzyme family
Magnaporthe grisea
metabolism
the enzyme plays an integral part in the biosynthesis of 1,8-dihydroxynaphthalene (DHN) melanin, a virulence factor of many filamentous fungi, together with scytalone dehydratase, pathway overview. DHN melanin biosynthesis constitutes a diversity-oriented metabolic network, comprising vicinal ketodiol and 4-hydroxy-1-tetralone biosyntheses as branching points. Polyhydroxynaphthalene reductases are involved in promiscuous reduction reactions, reflecting the idea of a matrix biosynthetic pathway, involvement of polyhydroxynaphthalene reductases in spirodioxynaphthalene biosynthesis
Magnaporthe grisea
physiological function
the enzyme plays an integral part in the biosynthesis of 1,8-dihydroxynaphthalene (DHN) melanin, a virulence factor of many filamentous fungi, togeher with scytalone dehydratase, pathway overview. Hundreds of metabolites, such as the dalmanols, balticols, 3,4-dihydroxy-1-tetralones, 4-hydroxy-1-tetralones, and spirodioxynaphthalenes are derived from the intermediate polyhydroxynaphthalenes
Magnaporthe grisea
Other publictions for EC 1.1.1.B57
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)
741603
Husain
Unprecedented role of hydrona ...
Magnaporthe grisea, Magnaporthe grisea ATCC MYA-4617
Angew. Chem. Int. Ed. Engl.
53
9806-9811
2014
-
-
-
-
-
-
-
-
-
-
-
4
-
2
-
-
-
1
-
-
-
-
14
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
4
-
-
-
-
-
-
-
-
14
-
-
-
-
-
-
-
-
-
-
3
3
-
-
-
742263
Roiban
CH-activating oxidative hydro ...
Bacillus megaterium, Bacillus megaterium ATCC 14581
Chem. Commun. (Camb.)
50
14310-14313
2014
-
1
-
-
5
-
-
-
-
-
-
4
-
2
-
-
-
-
-
-
-
-
11
-
-
-
-
-
-
-
-
1
-
-
-
-
1
-
1
-
5
-
-
-
-
-
-
-
-
4
-
-
-
-
-
-
-
-
11
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
728605
Vitale
Physicochemical characterizati ...
Pyrobaculum aerophilum, Pyrobaculum aerophilum DSM 7523
PLoS One
8
e63828
2013
-
1
-
1
-
-
3
-
-
-
-
-
-
4
-
-
-
-
-
-
-
-
2
-
-
-
-
-
-
-
-
1
-
-
3
-
1
-
1
1
-
-
3
3
-
-
-
-
-
-
-
-
-
-
-
-
-
-
2
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
727585
Vitale
Properties and evolution of an ...
Pyrobaculum aerophilum, Pyrobaculum aerophilum DSM 7523
Gene
461
26-31
2010
-
-
1
-
-
1
1
1
-
1
2
-
-
4
-
-
1
-
-
-
2
-
2
1
1
-
-
1
-
-
-
-
-
-
-
-
-
1
-
-
-
1
-
1
-
1
-
1
2
-
-
-
-
1
-
-
2
-
2
1
1
-
-
1
-
-
-
-
-
-
-
-
-
-