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Information on EC 1.1.1.B57 - 1-tetralone reductase [NADPH]
for references in articles please use BRENDA:EC1.1.1.B57preliminary BRENDA-supplied EC number
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1.1.1.B57 1-tetralone reductase [NADPH]Specify your search results
Word Map
The expected taxonomic range for this enzyme is: Eukaryota, Archaea
Synonyms
adhii, p450-bm3, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
ADHII
BG04_163
CYP102A1
MGG_02252
P450-BM3
PAE2687
PyAeADHII
T4HNR
tetrahydroxynaphthalene reductase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
1-tetralone + NADPH + H+ = 1-tetralol + NADP+
-
-
-
-
1-tetralone + NADPH + H+ = 1-tetralol + NADP+
reaction mechanism, overview
1-tetralone + NADPH + H+ = 1-tetralol + NADP+
reaction mechanism, overview
Pyricularia grisea ATCC MYA-4617
-
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SYSTEMATIC NAME
IUBMB Comments
1-tetralol:NADP+ oxidoreductase
-
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
2,3-epoxy-1,4-naphthoquinone + NADPH + H+
(1aS,7R,7aS)-7-hydroxy-7,7a-dihydronaphtho[2,3-b]oxiren-2(1aH)-one + NADP+
2-hydroxy-1,4-naphthoquinone + 2 NADPH + H+
(3S,4R)-3,4-dihydroxy-1-tetralone + 2 NADP+
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
-
?
2-hydroxy-1,4-naphthoquinone + NADPH + H+
cis-3,4-dihydroxy-1-tetralone + NADP+
-
-
?
5-hydroxy-2,3-dihydronaphthalene-1,4-dione + NADPH + H+
(S)-4,8-dihydroxy-1-tetralone + NADP+
-
-
?
6-methoxy-1-tetralone + NADPH + H
(S)-4-hydroxy-6-methoxy-1-tetralone + NADP+
-
-
?
flaviolin + NADPH + H+
cis-(3S,4R)-4-hydroxyscytalone + NADP+
-
-
?
1,3,6,8-tetrahydroxynaphthalene + NADPH + H+
(R)-scytalone + NADP+
-
-
?
1,3,6,8-tetrahydroxynaphthalene + NADPH + H+
(R)-scytalone + NADP+
Pyricularia grisea ATCC MYA-4617
-
-
?
1,3,8-trihydroxynaphthalene + NADPH + H+
(R)-vermelone + NADP+
-
-
?
1,3,8-trihydroxynaphthalene + NADPH + H+
(R)-vermelone + NADP+
Pyricularia grisea ATCC MYA-4617
-
-
?
1-indanone + NADPH + H
3-hydroxy-1-indanone + NADP+
-
-
?
1-tetralone + NADPH + H
(S)-4-hydroxy-1-tetralone + NADP+
-
-
?
2,3-dihydronaphthalene-1,4-dione + NADPH + H+
(S)-4-hydroxy-1-tetralone + NADP+
-
-
?
2,3-dihydronaphthalene-1,4-dione + NADPH + H+
(S)-4-hydroxy-1-tetralone + NADP+
Pyricularia grisea ATCC MYA-4617
-
-
?
2,3-epoxy-1,4-naphthoquinone + NADPH + H+
(1aS,7R,7aS)-7-hydroxy-7,7a-dihydronaphtho[2,3-b]oxiren-2(1aH)-one + NADP+
-
-
?
2,3-epoxy-1,4-naphthoquinone + NADPH + H+
(1aS,7R,7aS)-7-hydroxy-7,7a-dihydronaphtho[2,3-b]oxiren-2(1aH)-one + NADP+
Pyricularia grisea ATCC MYA-4617
-
-
?
3,4-dihydro-1(2H)-naphthalenone + NADPH + H+
1,2,3,4-tetrahydronaphthalen-1-ol + NADP+
3,4-dihydro-1(2H)-naphthalenone i.e. alpha-tetralone. The enzyme does not show activity on a large number of alcohols, aldehydes or ketones. It is active only with alpha-tetralone as substrate
-
?
3,4-dihydro-1(2H)-naphthalenone + NADPH + H+
1,2,3,4-tetrahydronaphthalen-1-ol + NADP+
3,4-dihydro-1(2H)-naphthalenone i.e. alpha-tetralone. The enzyme does not show activity on a large number of alcohols, aldehydes or ketones. It is active only with alpha-tetralone as substrate
-
?
5-methoxy-1-tetralone + NADPH + H
(S)-4-hydroxy-5-methoxy-1-tetralone + NADP+
-
-
?
5-methoxy-1-tetralone + NADPH + H
(S)-4-hydroxy-5-methoxy-1-tetralone + NADP+
-
-
?
indane + NADPH + H+
(S)-4-hydroxy-indan + NADP+
-
-
?
tetralin + NADPH + H+
(S)-4-hydroxy-tetralin + 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
-
?
additional information
?
-
Pyricularia grisea ATCC MYA-4617
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
-
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
1,3,6,8-tetrahydroxynaphthalene + NADPH + H+
(R)-scytalone + NADP+
-
-
-
?
1,3,6,8-tetrahydroxynaphthalene + NADPH + H+
(R)-scytalone + NADP+
Pyricularia grisea ATCC MYA-4617
-
-
-
?
1,3,8-trihydroxynaphthalene + NADPH + H+
(R)-vermelone + NADP+
-
-
-
?
1,3,8-trihydroxynaphthalene + NADPH + H+
(R)-vermelone + NADP+
Pyricularia grisea ATCC MYA-4617
-
-
-
?
indane + NADPH + H+
(S)-4-hydroxy-indan + NADP+
-
-
-
?
tetralin + NADPH + H+
(S)-4-hydroxy-tetralin + NADP+
-
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
1-[2-(diphenylmethoxy)ethyl]-4-[(2E)-3-phenylprop-2-en-1-yl]piperazine
i.e. GBR12783
1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-[(2E)-3-phenylprop-2-en-1-yl]piperazine
-
1-[bis(4-fluorophenyl)methyl]-4-[(2E)-3-phenylprop-2-en-1-yl]piperazine
i.e. flunarizine
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.04
1-[2-(diphenylmethoxy)ethyl]-4-[(2E)-3-phenylprop-2-en-1-yl]piperazine
Pyrobaculum aerophilum
pH 7.5, 37°C
0.01
1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-[(2E)-3-phenylprop-2-en-1-yl]piperazine
Pyrobaculum aerophilum
pH 7.5, 37°C
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
evolution
metabolism
physiological function
evolution
enzyme T4HNR is a member of the short-chain dehydrogenases/ reductases (SDR) enzyme family
evolution
Pyricularia grisea ATCC MYA-4617
-
enzyme T4HNR is a member of the short-chain dehydrogenases/ reductases (SDR) enzyme family
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
metabolism
Pyricularia grisea ATCC MYA-4617
-
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
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
physiological function
Pyricularia grisea ATCC MYA-4617
-
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
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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). CPXB_BACMB
Bacillus megaterium (strain ATCC 14581 / DSM 32 / JCM 2506 / NBRC 15308 / NCIMB 9376 / NCTC 10342 / VKM B-512)
1049
0
117781
Swiss-Prot
-
T4HR_MAGO7
Magnaporthe oryzae (strain 70-15 / ATCC MYA-4617 / FGSC 8958)
283
0
30054
Swiss-Prot
other Location (Reliability: 2)
Q8ZUP0_PYRAE
Pyrobaculum aerophilum (strain ATCC 51768 / IM2 / DSM 7523 / JCM 9630 / NBRC 100827)
331
0
34658
TrEMBL
-
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
crystal structure of both wild-type and cobalt-substituted enzyme at 1.75 A and 2.20 A resolution, respectively. One metal ion per monomer is present only at the structural site. The co-crystal structure of the NADPH-bound form of the enzyme at 2.35 A resolution shows close structural conservation with horse ADH, despite the lack of a catalytic Zn2+. Modeling of 1-tetralone into the NADPH-bound structure suggests an arginine as a possible catalytic residue
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
A328F
site-directed mutagenesis, the mutant shows altered enantioselectivity compared to the wild-type enzyme
A328K
site-directed mutagenesis, the mutant shows altered enantioselectivity compared to the wild-type enzyme
A328R
site-directed mutagenesis, the mutant shows altered enantioselectivity compared to the wild-type enzyme
A328Y
site-directed mutagenesis, the mutant shows altered enantioselectivity compared to the wild-type enzyme
A328F
-
site-directed mutagenesis, the mutant shows altered enantioselectivity compared to the wild-type enzyme
A328K
-
site-directed mutagenesis, the mutant shows altered enantioselectivity compared to the wild-type enzyme
A328R
-
site-directed mutagenesis, the mutant shows altered enantioselectivity compared to the wild-type enzyme
A328Y
-
site-directed mutagenesis, the mutant shows altered enantioselectivity compared to the wild-type enzyme
additional information
additional information
mutants of enzyme P450-BM3 evolved by directed evolution are excellent catalysts in the CH-activating oxidative hydroxylation of 1-tetralone derivatives and of indanone, with unusually high regio- and enantioselectivity
additional information
-
mutants of enzyme P450-BM3 evolved by directed evolution are excellent catalysts in the CH-activating oxidative hydroxylation of 1-tetralone derivatives and of indanone, with unusually high regio- and enantioselectivity
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GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
analysis
synthesis
analysis
miniaturized assay for quantitative high-throughput screening, by monitoring NADPH oxidation as a decrease in A340 using a spectrophotometer
analysis
-
miniaturized assay for quantitative high-throughput screening, by monitoring NADPH oxidation as a decrease in A340 using a spectrophotometer
synthesis
P450-BM3 enzyme mutants are ueful for CH-activating oxidative hydroxylation of readily available 1-tetralone derivatives with high degrees of regio- and stereoselectivity, e.g. oxidative hydroxylation of indane and tetralin, an approach which is currently not possible using chiral synthetic CH-activating transition metal catalysts
synthesis
-
P450-BM3 enzyme mutants are ueful for CH-activating oxidative hydroxylation of readily available 1-tetralone derivatives with high degrees of regio- and stereoselectivity, e.g. oxidative hydroxylation of indane and tetralin, an approach which is currently not possible using chiral synthetic CH-activating transition metal catalysts
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Vitale, A.; Rosso, F.; Barbarisi, A.; Labella, T.; D'Auria, S.
Properties and evolution of an alcohol dehydrogenase from the Crenarchaeota Pyrobaculum aerophilum
Gene
461
26-31
2010
Pyrobaculum aerophilum (Q8ZUP0), Pyrobaculum aerophilum DSM 7523 (Q8ZUP0)
brenda
Vitale, A.; Thorne, N.; Lovell, S.; Battaile, K.P.; Hu, X.; Shen, M.; D'Auria, S.; Auld, D.S.
Physicochemical characterization of a thermostable alcohol dehydrogenase from Pyrobaculum aerophilum
PLoS One
8
e63828
2013
Pyrobaculum aerophilum (Q8ZUP0), Pyrobaculum aerophilum DSM 7523 (Q8ZUP0)
brenda
Husain, S.; Schaetzle, M.; Luedeke, S.; Mueller, M.
Unprecedented role of hydronaphthoquinone tautomers in biosynthesis
Angew. Chem. Int. Ed. Engl.
53
9806-9811
2014
Pyricularia grisea (Q12634), Pyricularia grisea ATCC MYA-4617 (Q12634)
brenda
Roiban, G.; Agudo, R.; Ilie, A.; Lonsdale, R.; Reetz, M.
CH-activating oxidative hydroxylation of 1-tetralones and related compounds with high regio- and stereoselectivity
Chem. Commun. (Camb.)
50
14310-14313
2014
Bacillus megaterium (P14779), Bacillus megaterium ATCC 14581 (P14779)
brenda
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