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Literature summary extracted from
- A G316A mutation of manganese lipoxygenase augments hydroperoxide isomerase activity: mechanism of biosynthesis of epoxyalcohols (2006), J. Biol. Chem., 281, 17612-17623.
Cloned(Commentary)
| EC Number | Cloned (Comment) | Organism |
|---|---|---|
| 1.13.11.45 | expressed in Pichia pastoris | Gaeumannomyces graminis |
| 4.2.1.92 | expression in Pichia pastoris | Gaeumannomyces graminis |
Protein Variants
| EC Number | Protein Variants | Comment | Organism |
|---|---|---|---|
| 1.13.11.45 | G316A | catalytically active, 7-8% of hydroperoxide isomerase activity | Gaeumannomyces graminis |
| 1.13.11.45 | G316T | catalytically inactive | Gaeumannomyces graminis |
| 1.13.11.45 | G316V | catalytically inactive | Gaeumannomyces graminis |
| 4.2.1.92 | G316A | the G316A mutant increases the oxygenation at the n-8 carbon of 17:3n-3 and at the n-10 carbon of the C17 and C18 fatty acids (from 12% to 711%). The most striking effect of the G316A mutant is a 2-, 7-, and 15-fold increase in transformation of the n-6 hydroperoxides of 19:3n-3, 18:3n-3, and 17:3n-3, respectively, to keto fatty acids and epoxyalcohols. G316A mutant augments the hydroperoxide isomerase activity by positioning the hydroperoxy group at the n-6 carbon of n-3 fatty acids closer to the reduced catalytic metal | Gaeumannomyces graminis |
| 4.2.1.92 | G316S | inactive mutant enzyme | Gaeumannomyces graminis |
| 4.2.1.92 | G316T | inactive mutant enzyme | Gaeumannomyces graminis |
| 4.2.1.92 | G316V | inactivfe mutant enzyme | Gaeumannomyces graminis |
Inhibitors
| EC Number | Inhibitors | Comment | Organism | Structure |
|---|---|---|---|---|
| 1.13.11.45 | eicosatetraynoic acid | 0.1 mM, 75% inhibition | Gaeumannomyces graminis |  |
| 1.13.11.45 | N-(3-phenoxycinnamyl) acetohydroxamic acid | 0.3 mM, complete inhibition | Gaeumannomyces graminis | |
KM Value [mM]
| EC Number | KM Value [mM] | KM Value Maximum [mM] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|---|
| 1.13.11.45 | 0.01 | - |
(13R)-hydroperoxylinolenic acid | mutant enzyme G316A | Gaeumannomyces graminis | |
Metals/Ions
| EC Number | Metals/Ions | Comment | Organism | Structure |
|---|---|---|---|---|
| 1.13.11.45 | Mn2+ | - |
Gaeumannomyces graminis | |
Organism
| EC Number | Organism | UniProt | Comment | Textmining |
|---|---|---|---|---|
| 1.13.11.45 | Gaeumannomyces graminis | Q8X151 | variant avenae | - |
| 4.2.1.92 | Gaeumannomyces graminis | Q8X151 | var. avenae | - |
Purification (Commentary)
| EC Number | Purification (Comment) | Organism |
|---|---|---|
| 1.13.11.45 | phenyl-Sepharose column chromatography | Gaeumannomyces graminis |
| 4.2.1.92 | - |
Gaeumannomyces graminis |
Substrates and Products (Substrate)
| EC Number | Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|---|
| 1.13.11.45 | (13R)-hydroperoxylinolenic acid + O2 | only mutant enzyme G316A | Gaeumannomyces graminis | 13-ketolinolenic acid + epoxyalcohols | erythro- and threo-11-hydroxy-(12R,13R)-epoxy-(9Z,15Z)-octadecadienoic acids and one of the corresponding cis-epoxides as major products | ? | |
| 1.13.11.45 | linoleic acid + O2 | - |
Gaeumannomyces graminis | (9Z,11E)-(13R)-hydroperoxyoctadecadienoic acid | - |
? | |
| 4.2.1.92 | (13R)-hydroperoxylinolenic acid | the G316A mutant converts (13R)-hydroperoxylinolenic acid to 13-ketolinolenic acid (with an apparent Km of 0.01 mM) and to epoxyalcohols viz. erythro- and threo-11-hydroxy-(12R,13R)-epoxy-(9Z,15Z)-octadecadienoic acids and one of the corresponding cis-epoxides as major products | Gaeumannomyces graminis | 13-ketolinolenic acid + threo-11-hydroxy-(12R,13R)-epoxy-(9Z,15Z)-octadecadienoic acid + erythro-11-hydroxy-(12R,13R)-epoxy-(9Z,15Z)-octadecadienoic acid | - |
? | |
| 4.2.1.92 | heptadecatrienoic acid | the G316A mutant transforms 17:3n-3 to both 12-hydroperoxyheptadecatrienoic acid (about 93%) and 10-hydroperoxyheptadecatrienoic acid (7%) | Gaeumannomyces graminis | 12-hydroperoxyheptadecatrienoic acid + (8Z,10S,11Z,14Z)-10-hydroperoxyheptadeca-8,11,14-trienoic acid | - |
? | |
| 4.2.1.92 | linoleic acid | Mn-LO G316A metabolizeS 18:2n-6 to (11S)-hydroperoxyoctadecadienoic acid and (13R)-hydroperoxyoctadecadienoic acid in approximately the same relative amounts as the native enzyme, and (13R)-hydroperoxyoctadecadienoic acid accumulates as the end product | Gaeumannomyces graminis | ? | - |
? | |
| 4.2.1.92 | linolenic acid | Mn-LO G316A metabolizes 18:3n-3 to (13R)-hydroperoxyoctadecatrienoic acid and (11S)-hydroperoxyoctadecatrienoic acid | Gaeumannomyces graminis | (13R)-hydroperoxyoctadecatrienoic acid + (11S)-hydroperoxyoctadecatrienoic acid | - |
? | |
| 4.2.1.92 | additional information | catalytic properties of Mn-LO and the G316A mutant with heptadecatrienic acid, 18:2n-6, octadecatrienoic acid, and nonadecatrienoic acid as substrates: increasing the fatty acid chain length from C17 to C19 shifts the oxygenation by Mn-LO from the n-6 toward the n-8 carbon. The G316A mutant increases the oxygenation at the n-8 carbon of 17:3n-3 and at the n-10 carbon of the C17 and C18 fatty acids (from 12% to 711%). The most striking effect of the G316A mutant is a 2fold, 7fold, and 15fold increase in transformation of the n-6 hydroperoxides of 19:3n-3, 18:3n-3, and 17:3n-3, respectively, to keto fatty acids and epoxyalcohols. The n-3 double bond is essential. Both oxygen atoms are retained in the epoxyalcohols. (R)-Hydroperoxides at n-6 of C17:3, 18:3, and 19:3 are transformed 5times faster than (S)-stereoisomers | Gaeumannomyces graminis | ? | - |
? | |
Synonyms
| EC Number | Synonyms | Comment | Organism |
|---|---|---|---|
| 1.13.11.45 | Mn-LO | - |
Gaeumannomyces graminis |
| 4.2.1.92 | Mn-LO | - |
Gaeumannomyces graminis |
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