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Literature summary extracted from

  • Schaetzle, M.A.; Flemming, S.; Husain, S.M.; Richter, M.; Guenther, S.; Mueller, M.
    Tetrahydroxynaphthalene reductase: catalytic properties of an enzyme involved in reductive asymmetric naphthol dearomatization (2012), Angew. Chem. Int. Ed. Engl., 51, 2643-2646.
    View publication on PubMed

Protein Variants

EC Number Protein Variants Comment Organism
1.1.1.252 additional information generation of the C-terminally Ile274-truncated variant T4HNR(1-273) Pyricularia grisea

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.1.1.252 1,3,6,8-tetrahydroxynaphthalene + NADPH + H+ Pyricularia grisea reduction reaction via the via the 3-keto tautomer of 1,3,6,8-tetrahydroxynaphthalene scytalone + NADP+
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 ?

Organism

EC Number Organism UniProt Comment Textmining
1.1.1.252 Pyricularia grisea
-
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.1.1.252 1,3,6,8-tetrahydroxynaphthalene + NADPH + H+ reduction reaction via the via the 3-keto tautomer of 1,3,6,8-tetrahydroxynaphthalene Pyricularia grisea scytalone + NADP+
-
 ?
1.1.1.252 1,3,6,8-tetrahydroxynaphthalene + NADPH + H+ with enatiomeric excess of over 95%, reduction reaction via the via the 3-oxo tautomer of 1,3,6,8-tetrahydroxynaphthalene Pyricularia grisea scytalone + NADP+
-
 ?
1.1.1.252 1,3,6-trihydroxynaphthalene + NADPH + H+
-
 Pyricularia grisea (R)-8-deoxyscytalone + NADP+
-
 ?
1.1.1.252 1,3-dihydroxynaphthalene + NADPH + H+ very low activity Pyricularia grisea 3-hydroxy-3,4-dihydronaphthalen-1(2H)-one + NADP+
-
 ?
1.1.1.252 2-methylcyclohexanone + NADPH + H+
-
 Pyricularia grisea trans-2-methylcyclohexanol + NADP+
-
 ?
1.1.1.252 2-tetralone + NADPH + H+ high activity, almost complete conversion Pyricularia grisea 2-tetralol + NADP+
-
 ?
1.1.1.252 5-hydroxy-2-tetralone + NADPH + H+
-
 Pyricularia grisea 5-hydroxy-2-tetralol + NADP+
-
 ?
1.1.1.252 5-methoxy-2-tetralone + NADPH + H+ high activity, almost complete conversion Pyricularia grisea 5-methoxy-2-tetralol + NADP+
-
 ?
1.1.1.252 6-hydroxy-2-tetralone + NADPH + H+
-
 Pyricularia grisea 6-hydroxy-2-tetralol + NADP+
-
 ?
1.1.1.252 6-methoxy-2-tetralone + NADPH + H+
-
 Pyricularia grisea 6-methoxy-2-tetralol + NADP+
-
 ?
1.1.1.252 7-hydroxy-2-tetralone + NADPH + H+ high activity, almost complete conversion Pyricularia grisea 7-hydroxy-2-tetralol + NADP+
-
 ?
1.1.1.252 7-methoxy-2-tetralone + NADPH + H+ high activity, almost complete conversion Pyricularia grisea 7-methoxy-2-tetralol + NADP+
-
 ?
1.1.1.252 8-hydroxy-2-tetralone + NADPH + H+ high activity, almost complete conversion Pyricularia grisea 8-hydroxy-2-tetralol + NADP+
-
 ?
1.1.1.252 8-methoxy-2-tetralone + NADPH + H+ high activity, almost complete conversion Pyricularia grisea 8-methoxy-2-tetralol + NADP+
-
 ?

Synonyms

EC Number Synonyms Comment Organism
1.1.1.252 T4HNR
-
 Pyricularia grisea

Cofactor

EC Number Cofactor Comment Organism Structure
1.1.1.252 NADPH
-
 Pyricularia grisea

General Information

EC Number General Information Comment Organism
1.1.1.252 evolution the enzyme is a member of the short-chain dehydrogenase/reductase (SDR) family of enzymes Pyricularia grisea
1.1.1.252 metabolism the enzyme catalyzes a step in 1,8-dihydroxynaphthalene-melanin biosynthesis, overview Pyricularia grisea
1.1.1.252 additional information structure-activity relationship of T4HNR and dynamics of its catalytic cycle, substrate docking study, the carboxylate of Ile274 might have an impact on substrate orientation, overview. Two orientations of tetralones in the active site of T4HNR revealed by docking studies: 1. si-face orientation (representing the preferential hydrophobic interaction of the methoxy group of substrate 5-methoxy-2-tetralone) and 2. the re-face orientation Pyricularia grisea