BRENDA - Enzyme Database
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
ID
1,3,6,8-tetrahydroxynaphthalene + NADPH + H+
Pyricularia grisea
-
(R)-scytalone + NADP+
-
-
?
1,3,6,8-tetrahydroxynaphthalene + NADPH + H+
Pyricularia grisea ATCC MYA-4617
-
(R)-scytalone + NADP+
-
-
?
1,3,8-trihydroxynaphthalene + NADPH + H+
Pyricularia grisea
-
(R)-vermelone + NADP+
-
-
?
1,3,8-trihydroxynaphthalene + NADPH + H+
Pyricularia grisea ATCC MYA-4617
-
(R)-vermelone + NADP+
-
-
?
Organism
Organism
UniProt
Commentary
Textmining
Pyricularia grisea
Q12634
-
-
Pyricularia grisea ATCC MYA-4617
Q12634
-
-
Reaction
Reaction
Commentary
Organism
Reaction ID
1-tetralone + NADPH + H+ = 1-tetralol + NADP+
reaction mechanism, overview
Pyricularia grisea
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
Substrate Product ID
1,3,6,8-tetrahydroxynaphthalene + NADPH + H+
-
741603
Pyricularia grisea
(R)-scytalone + NADP+
-
-
-
?
1,3,6,8-tetrahydroxynaphthalene + NADPH + H+
-
741603
Pyricularia grisea ATCC MYA-4617
(R)-scytalone + NADP+
-
-
-
?
1,3,8-trihydroxynaphthalene + NADPH + H+
-
741603
Pyricularia grisea
(R)-vermelone + NADP+
-
-
-
?
1,3,8-trihydroxynaphthalene + NADPH + H+
-
741603
Pyricularia grisea ATCC MYA-4617
(R)-vermelone + NADP+
-
-
-
?
2,3-dihydronaphthalene-1,4-dione + NADPH + H+
-
741603
Pyricularia grisea
(S)-4-hydroxy-1-tetralone + NADP+
-
-
-
?
2,3-dihydronaphthalene-1,4-dione + NADPH + H+
-
741603
Pyricularia grisea ATCC MYA-4617
(S)-4-hydroxy-1-tetralone + NADP+
-
-
-
?
2,3-epoxy-1,4-naphthoquinone + NADPH + H+
-
741603
Pyricularia 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
Pyricularia 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
Pyricularia grisea
(3S,4R)-3,4-dihydroxy-1-tetralone + 2 NADP+
-
-
-
?
2-hydroxy-1,4-naphthoquinone + NADPH + H+
-
741603
Pyricularia grisea
cis-3,4-dihydroxy-1-tetralone + NADP+
-
-
-
?
5-hydroxy-2,3-dihydronaphthalene-1,4-dione + NADPH + H+
-
741603
Pyricularia grisea
(S)-4,8-dihydroxy-1-tetralone + NADP+
-
-
-
?
flaviolin + NADPH + H+
-
741603
Pyricularia 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
Pyricularia 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
Pyricularia grisea ATCC MYA-4617
?
-
-
-
-
Synonyms
Synonyms
Commentary
Organism
MGG_02252
-
Pyricularia grisea
T4HNR
-
Pyricularia grisea
tetrahydroxynaphthalene reductase
-
Pyricularia grisea
Cofactor
Cofactor
Commentary
Organism
Structure
NADPH
-
Pyricularia grisea
Cofactor (protein specific)
Cofactor
Commentary
Organism
Structure
NADPH
-
Pyricularia grisea
Natural Substrates/ Products (Substrates) (protein specific)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
ID
1,3,6,8-tetrahydroxynaphthalene + NADPH + H+
Pyricularia grisea
-
(R)-scytalone + NADP+
-
-
?
1,3,6,8-tetrahydroxynaphthalene + NADPH + H+
Pyricularia grisea ATCC MYA-4617
-
(R)-scytalone + NADP+
-
-
?
1,3,8-trihydroxynaphthalene + NADPH + H+
Pyricularia grisea
-
(R)-vermelone + NADP+
-
-
?
1,3,8-trihydroxynaphthalene + NADPH + H+
Pyricularia 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
ID
1,3,6,8-tetrahydroxynaphthalene + NADPH + H+
-
741603
Pyricularia grisea
(R)-scytalone + NADP+
-
-
-
?
1,3,6,8-tetrahydroxynaphthalene + NADPH + H+
-
741603
Pyricularia grisea ATCC MYA-4617
(R)-scytalone + NADP+
-
-
-
?
1,3,8-trihydroxynaphthalene + NADPH + H+
-
741603
Pyricularia grisea
(R)-vermelone + NADP+
-
-
-
?
1,3,8-trihydroxynaphthalene + NADPH + H+
-
741603
Pyricularia grisea ATCC MYA-4617
(R)-vermelone + NADP+
-
-
-
?
2,3-dihydronaphthalene-1,4-dione + NADPH + H+
-
741603
Pyricularia grisea
(S)-4-hydroxy-1-tetralone + NADP+
-
-
-
?
2,3-dihydronaphthalene-1,4-dione + NADPH + H+
-
741603
Pyricularia grisea ATCC MYA-4617
(S)-4-hydroxy-1-tetralone + NADP+
-
-
-
?
2,3-epoxy-1,4-naphthoquinone + NADPH + H+
-
741603
Pyricularia 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
Pyricularia 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
Pyricularia grisea
(3S,4R)-3,4-dihydroxy-1-tetralone + 2 NADP+
-
-
-
?
2-hydroxy-1,4-naphthoquinone + NADPH + H+
-
741603
Pyricularia grisea
cis-3,4-dihydroxy-1-tetralone + NADP+
-
-
-
?
5-hydroxy-2,3-dihydronaphthalene-1,4-dione + NADPH + H+
-
741603
Pyricularia grisea
(S)-4,8-dihydroxy-1-tetralone + NADP+
-
-
-
?
flaviolin + NADPH + H+
-
741603
Pyricularia 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
Pyricularia 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
Pyricularia 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
Pyricularia 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
Pyricularia 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
Pyricularia grisea
General Information (protein specific)
General Information
Commentary
Organism
evolution
enzyme T4HNR is a member of the short-chain dehydrogenases/ reductases (SDR) enzyme family
Pyricularia 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
Pyricularia 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
Pyricularia 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
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)
741603
Husain
Unprecedented role of hydrona ...
Pyricularia grisea, Pyricularia grisea ATCC MYA-4617
Angew. Chem. Int. Ed. Engl.
53
9806-9811
2014
-
-
-
-
-
-
-
-
-
-
-
4
-
2
-
-
-
1
-
-
-
-
14
-
3
-
-
-
-
-
-
-
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
-
4
-
-
-
-
-
-
-
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
-
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
2
1
-
-
1
-
-
-
-
-
-
-
-
-
1
-
-
-
1
-
1
-
1
-
1
2
-
-
-
-
1
-
-
2
-
2
1
1
-
-
1
-
-
-
-
-
-
-
-
-
-