1.1.1.B57: 1-tetralone reductase [NADPH]
This is an abbreviated version!
For detailed information about 1-tetralone reductase [NADPH], go to the full flat file.
Word Map on EC 1.1.1.B57
Reaction
Synonyms
ADHII, MGG_02252, PAE2687, PyAeADHII, T4HNR, tetrahydroxynaphthalene reductase
ECTree
1.1.1.B57 1-tetralone reductase [NADPH]Advanced search results
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results (Substrates Products
Substrates Products on EC 1.1.1.B57 - 1-tetralone reductase [NADPH]
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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
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-
?
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+
-
-
-
?
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
-
-
-
?
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
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-
?
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
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?
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
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?
additional information
?
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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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?
