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Literature summary extracted from

  • Matsuda, Y.; Awakawa, T.; Wakimoto, T.; Abe, I.
    Spiro-ring formation is catalyzed by a multifunctional dioxygenase in austinol biosynthesis (2013), J. Am. Chem. Soc., 135, 10962-10965 .
    View publication on PubMed

Metals/Ions

EC Number Metals/Ions Comment Organism Structure
1.14.20.B4 Iron
-
 Aspergillus nidulans

Organism

EC Number Organism UniProt Comment Textmining
1.14.20.B4 Aspergillus nidulans Q5AR34
-
-
1.14.20.B4 Aspergillus nidulans ATCC 38163 Q5AR34
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.14.20.B4 berkeyleyone A + 2-oxoglutarate + O2
-
 Aspergillus nidulans 5-hydroxyberkeyleyone A + succinate + CO2 + H2O
-
 ?
1.14.20.B4 berkeyleyone A + 2-oxoglutarate + O2
-
 Aspergillus nidulans ATCC 38163 5-hydroxyberkeyleyone A + succinate + CO2 + H2O
-
 ?
1.14.20.B4 berkeyleyone A + 2-oxoglutarate + O2
-
 Aspergillus nidulans preaustinoid A + succinate + CO2 + H2O
-
 ?
1.14.20.B4 berkeyleyone A + 2-oxoglutarate + O2
-
 Aspergillus nidulans ATCC 38163 preaustinoid A + succinate + CO2 + H2O
-
 ?
1.14.20.B4 preaustinoid A + 2-oxoglutarate + O2
-
 Aspergillus nidulans preaustinoid C + succinate + CO2 + H2O
-
 ?
1.14.20.B4 preaustinoid A + 2-oxoglutarate + O2
-
 Aspergillus nidulans ATCC 38163 preaustinoid C + succinate + CO2 + H2O
-
 ?
1.14.20.B4 preaustinoid A1 + 2-oxoglutarate + O2
-
 Aspergillus nidulans preaustinoid A2 + succinate + CO2 + H2O
-
 ?
1.14.20.B4 preaustinoid A1 + 2-oxoglutarate + O2
-
 Aspergillus nidulans ATCC 38163 preaustinoid A2 + succinate + CO2 + H2O
-
 ?
1.14.20.B4 preaustinoid A2 + 2-oxoglutarate + O2 spiro-ring formation Aspergillus nidulans preaustinoid A3 + succinate + CO2 + H2O
-
 ?
1.14.20.B4 preaustinoid A2 + 2-oxoglutarate + O2 spiro-ring formation Aspergillus nidulans ATCC 38163 preaustinoid A3 + succinate + CO2 + H2O
-
 ?
1.14.20.B4 preaustinoid C + 2-oxoglutarate + O2
-
 Aspergillus nidulans austinoid C + succinate + CO2 + H2O
-
 ?

Synonyms

EC Number Synonyms Comment Organism
1.14.20.B4 AusE
-
 Aspergillus nidulans

General Information

EC Number General Information Comment Organism
1.14.20.B4 metabolism AusE has a conserved 2-His-1-carboxylate iron-binding facial triad H130, D132, H214. In the mechanism for the oxidative spiro-ring formation, the initial binding of 2-oxoglutarate and O2 leads to oxidative decarboxylation of 2-oxoglutarate, generating the active Fe(IV)-oxo species, which hydroxylates the enone preaustinoid A2 at C5, forming the hydroxylated intermediate bound to an Fe(II) species. Elimination of the hydroxyl group followed by rearrangement of the carbon skeleton of the resulting carbocationic intermediate generates the spiro-lactone preaustinoid A3 Aspergillus nidulans
1.14.20.B4 physiological function AusE is involved in conversion of protoausteroid A into preaustinoid A3, a precursor of austinol. AusE iteratively catalyzes multistep oxidation reactions, including stereospecific spiro-lactone ring-forming reaction Aspergillus nidulans