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Literature summary for 4.2.1.92 extracted from

  • Yoeun, S.; Rakwal, R.; Han, O.
    Dual positional substrate specificity of rice allene oxide synthase-1: insight into mechanism of inhibition by type II ligand imidazole (2013), BMB Rep., 46, 151-156.
    View publication on PubMedView publication on EuropePMC
Search for more literature for 4.2.1.92

Activating Compound

Activating Compound Comment Organism Structure
cytochrome P450 AOS is a non-classical cytochrome P450, which, like other CYP74 enzymes, does not require molecular oxygen and NADPH-dependent P450 reductase Oryza sativa

Inhibitors

Inhibitors Comment Organism Structure
imidazole imidazole may coordinate to ferric heme iron, triggering a heme-iron transition from high spin state to low spin state Oryza sativa

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.0069
-
 (9S)-hydroperoxyoctadecadienoic acid pH 7.5, 22°C Oryza sativa
0.0086
-
 (9S)-hydroperoxyoctadecatrienoic acid pH 7.5, 22°C Oryza sativa
0.0123
-
 (13S)-hydroperoxyoctadecadienoic acid pH 7.5, 22°C Oryza sativa
0.0125
-
 (13S)-hydroperoxyoctadecatrienoic acid pH 7.5, 22°C Oryza sativa

Metals/Ions

Metals/Ions Comment Organism Structure
Fe2+ ferric heme iron Oryza sativa

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
additional information Oryza sativa cleavage of 9-hydroperoxy fatty acids in vivo, AOS enzymes also convert hydroperoxy fatty acids to aldehydes via an HPL-like activity ?
-
 ?

Organism

Organism UniProt Comment Textmining
Oryza sativa
-
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(13S)-hydroperoxyoctadecadienoic acid
-
 Oryza sativa 13-hydroxy-12-oxo-9(Z)-octadecenoic acid + 12-oxo-10-phytoenoic acid 13-hydroxy-12-oxo-(9Z)-octadecenoic acid is the major product ?
(13S)-hydroperoxyoctadecatrienoic acid
-
 Oryza sativa 13-hydroxy-12-oxo-(9Z,15Z)-octadecadienoic acid + 12-oxo-(10Z,15Z)-phytodienoic acid OsAOS1 produces a 1:1 racemic mixture of cis-(+)/cis-(-)-12-oxo-(10Z,15Z)-phytodienoic acid via non-enzymatic cyclization of 12,13-epoxy-9,11,15-octadecatrienoic acid, an unstable allene oxide ?
(9S)-hydroperoxyoctadecadienoic acid
-
 Oryza sativa ?
-
 ?
(9S)-hydroperoxyoctadecatrienoic acid
-
 Oryza sativa ?
-
 ?
additional information cleavage of 9-hydroperoxy fatty acids in vivo, AOS enzymes also convert hydroperoxy fatty acids to aldehydes via an HPL-like activity Oryza sativa ?
-
 ?
additional information allene oxide synthase converts fatty acid hydroperoxides into unstable fatty acid epoxides (allene oxides). OsAOS1 exhibits dual positional substrate specificity and prefers 13-positional isomeric to 9-positional isomeric substrates in vitro. OsAOS1 converts (9S)-hydroperoxyoctadecadienoic acid or (9S)-hydroperoxyoctadecatrienoic acid into the corresponding unstable allene oxides, which are non-enzymatically transformed into a 9alpha-ketol as the major product, and 13gamma-ketols and cyclopentenone derivatives as minor products Oryza sativa ?
-
 ?

Synonyms

Synonyms Comment Organism
allene oxide synthase-1
-
 Oryza sativa
CYP74
-
 Oryza sativa
OsAOS1
-
 Oryza sativa

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
22
-
 assay at room temperature Oryza sativa

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
17.5
-
 (9S)-hydroperoxyoctadecatrienoic acid pH 7.5, 22°C Oryza sativa
44.9
-
 (9S)-hydroperoxyoctadecadienoic acid pH 7.5, 22°C Oryza sativa
494.5
-
 (13S)-hydroperoxyoctadecadienoic acid pH 7.5, 22°C Oryza sativa
537.8
-
 (13S)-hydroperoxyoctadecatrienoic acid pH 7.5, 22°C Oryza sativa

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7.5
-
 assay at Oryza sativa

General Information

General Information Comment Organism
evolution AOS is a non-classical cytochrome P450, which, like other CYP74 enzymes, does not require molecular oxygen and NADPH-dependent P450 reductase Oryza sativa
additional information putative type II ligand-induced spin state transition in OsAOS1 Oryza sativa

kcat/KM [mM/s]

kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
2000
-
 (9S)-hydroperoxyoctadecatrienoic acid pH 7.5, 22°C Oryza sativa
6500
-
 (9S)-hydroperoxyoctadecadienoic acid pH 7.5, 22°C Oryza sativa
39600
-
 (13S)-hydroperoxyoctadecadienoic acid pH 7.5, 22°C Oryza sativa
43700
-
 (13S)-hydroperoxyoctadecatrienoic acid pH 7.5, 22°C Oryza sativa