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Literature summary for 1.1.1.B57 extracted from

  • Husain, S.; Schaetzle, M.; Luedeke, S.; Mueller, M.
    Unprecedented role of hydronaphthoquinone tautomers in biosynthesis (2014), Angew. Chem. Int. Ed. Engl., 53, 9806-9811 .
    View publication on PubMed
Search for more literature for 1.1.1.B57

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1,3,6,8-tetrahydroxynaphthalene + NADPH + H+ Pyricularia grisea
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 (R)-scytalone + NADP+
-
 ?
1,3,6,8-tetrahydroxynaphthalene + NADPH + H+ Pyricularia grisea ATCC MYA-4617
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 (R)-scytalone + NADP+
-
 ?
1,3,8-trihydroxynaphthalene + NADPH + H+ Pyricularia grisea
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 (R)-vermelone + NADP+
-
 ?
1,3,8-trihydroxynaphthalene + NADPH + H+ Pyricularia grisea ATCC MYA-4617
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 (R)-vermelone + NADP+
-
 ?

Organism

Organism UniProt Comment Textmining
Pyricularia grisea Q12634
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Pyricularia grisea ATCC MYA-4617 Q12634
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-

Reaction

Reaction Comment Organism Reaction ID
1-tetralone + NADPH + H+ = 1-tetralol + NADP+ reaction mechanism, overview Pyricularia grisea
a

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1,3,6,8-tetrahydroxynaphthalene + NADPH + H+
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 Pyricularia grisea (R)-scytalone + NADP+
-
 ?
1,3,6,8-tetrahydroxynaphthalene + NADPH + H+
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 Pyricularia grisea ATCC MYA-4617 (R)-scytalone + NADP+
-
 ?
1,3,8-trihydroxynaphthalene + NADPH + H+
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 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+
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 Pyricularia grisea (S)-4-hydroxy-1-tetralone + NADP+
-
 ?
2,3-dihydronaphthalene-1,4-dione + NADPH + H+
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 Pyricularia grisea ATCC MYA-4617 (S)-4-hydroxy-1-tetralone + NADP+
-
 ?
2,3-epoxy-1,4-naphthoquinone + NADPH + H+
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 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+
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 ?
2-hydroxy-1,4-naphthoquinone + NADPH + H+
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 Pyricularia grisea cis-3,4-dihydroxy-1-tetralone + NADP+
-
 ?
5-hydroxy-2,3-dihydronaphthalene-1,4-dione + NADPH + H+
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 Pyricularia grisea (S)-4,8-dihydroxy-1-tetralone + NADP+
-
 ?
flaviolin + NADPH + H+
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 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 ?
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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 Pyricularia grisea ATCC MYA-4617 ?
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 ?

Synonyms

Synonyms Comment Organism
MGG_02252
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 Pyricularia grisea
T4HNR
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 Pyricularia grisea
tetrahydroxynaphthalene reductase
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 Pyricularia grisea

Cofactor

Cofactor Comment Organism Structure
NADPH
-
 Pyricularia grisea

General Information

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