Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
---|---|---|---|---|---|---|
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 | UniProt | Comment | Textmining |
---|---|---|---|
Pyricularia grisea | Q12634 | - |
- |
Pyricularia grisea ATCC MYA-4617 | Q12634 | - |
- |
Reaction | Comment | Organism | Reaction ID |
---|---|---|---|
1-tetralone + NADPH + H+ = 1-tetralol + NADP+ | reaction mechanism, overview | Pyricularia grisea |
Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
---|---|---|---|---|---|---|
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+ | - |
? | |
2,3-dihydronaphthalene-1,4-dione + NADPH + H+ | - |
Pyricularia grisea | (S)-4-hydroxy-1-tetralone + NADP+ | - |
? | |
2,3-dihydronaphthalene-1,4-dione + NADPH + H+ | - |
Pyricularia grisea ATCC MYA-4617 | (S)-4-hydroxy-1-tetralone + NADP+ | - |
? | |
2,3-epoxy-1,4-naphthoquinone + NADPH + H+ | - |
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+ | - |
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 | Pyricularia grisea | (3S,4R)-3,4-dihydroxy-1-tetralone + 2 NADP+ | - |
? | |
2-hydroxy-1,4-naphthoquinone + NADPH + H+ | - |
Pyricularia grisea | cis-3,4-dihydroxy-1-tetralone + NADP+ | - |
? | |
5-hydroxy-2,3-dihydronaphthalene-1,4-dione + NADPH + H+ | - |
Pyricularia grisea | (S)-4,8-dihydroxy-1-tetralone + NADP+ | - |
? | |
flaviolin + NADPH + H+ | - |
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 | 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 | Pyricularia grisea ATCC MYA-4617 | ? | - |
? |
Synonyms | Comment | Organism |
---|---|---|
MGG_02252 | - |
Pyricularia grisea |
T4HNR | - |
Pyricularia grisea |
tetrahydroxynaphthalene reductase | - |
Pyricularia grisea |
Cofactor | Comment | Organism | Structure |
---|---|---|---|
NADPH | - |
Pyricularia grisea |
General Information | Comment | 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 |