BRENDA - Enzyme Database show
show all sequences of 4.2.1.92

A G316A mutation of manganese lipoxygenase augments hydroperoxide isomerase activity: mechanism of biosynthesis of epoxyalcohols

Cristea, M.; Oliw, E.H.; J. Biol. Chem. 281, 17612-17623 (2006)

Data extracted from this reference:

Cloned(Commentary)
Commentary
Organism
expression in Pichia pastoris
Gaeumannomyces graminis
Engineering
Amino acid exchange
Commentary
Organism
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 1–2% to 7–11%). 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
G316S
inactive mutant enzyme
Gaeumannomyces graminis
G316T
inactive mutant enzyme
Gaeumannomyces graminis
G316V
inactivfe mutant enzyme
Gaeumannomyces graminis
Organism
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
Gaeumannomyces graminis
Q8X151
var. avenae
-
Purification (Commentary)
Commentary
Organism
-
Gaeumannomyces graminis
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
(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
674584
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
-
-
-
?
heptadecatrienoic acid
the G316A mutant transforms 17:3n-3 to both 12-hydroperoxyheptadecatrienoic acid (about 93%) and 10-hydroperoxyheptadecatrienoic acid (7%)
674584
Gaeumannomyces graminis
12-hydroperoxyheptadecatrienoic acid + (8Z,10S,11Z,14Z)-10-hydroperoxyheptadeca-8,11,14-trienoic acid
-
-
-
?
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
674584
Gaeumannomyces graminis
?
-
-
-
?
linolenic acid
Mn-LO G316A metabolizes 18:3n-3 to (13R)-hydroperoxyoctadecatrienoic acid and (11S)-hydroperoxyoctadecatrienoic acid
674584
Gaeumannomyces graminis
(13R)-hydroperoxyoctadecatrienoic acid + (11S)-hydroperoxyoctadecatrienoic acid
-
-
-
?
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 1–2% to 7–11%). 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
674584
Gaeumannomyces graminis
?
-
-
-
-
Cloned(Commentary) (protein specific)
Commentary
Organism
expression in Pichia pastoris
Gaeumannomyces graminis
Engineering (protein specific)
Amino acid exchange
Commentary
Organism
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 1–2% to 7–11%). 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
G316S
inactive mutant enzyme
Gaeumannomyces graminis
G316T
inactive mutant enzyme
Gaeumannomyces graminis
G316V
inactivfe mutant enzyme
Gaeumannomyces graminis
Purification (Commentary) (protein specific)
Commentary
Organism
-
Gaeumannomyces graminis
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
(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
674584
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
-
-
-
?
heptadecatrienoic acid
the G316A mutant transforms 17:3n-3 to both 12-hydroperoxyheptadecatrienoic acid (about 93%) and 10-hydroperoxyheptadecatrienoic acid (7%)
674584
Gaeumannomyces graminis
12-hydroperoxyheptadecatrienoic acid + (8Z,10S,11Z,14Z)-10-hydroperoxyheptadeca-8,11,14-trienoic acid
-
-
-
?
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
674584
Gaeumannomyces graminis
?
-
-
-
?
linolenic acid
Mn-LO G316A metabolizes 18:3n-3 to (13R)-hydroperoxyoctadecatrienoic acid and (11S)-hydroperoxyoctadecatrienoic acid
674584
Gaeumannomyces graminis
(13R)-hydroperoxyoctadecatrienoic acid + (11S)-hydroperoxyoctadecatrienoic acid
-
-
-
?
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 1–2% to 7–11%). 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
674584
Gaeumannomyces graminis
?
-
-
-
-
Other publictions for EC 4.2.1.92
No.
1st author
Pub Med
title
organims
journal
volume
pages
year
Activating Compound
Application
Cloned(Commentary)
Crystallization (Commentary)
Engineering
General Stability
Inhibitors
KM Value [mM]
Localization
Metals/Ions
Molecular Weight [Da]
Natural Substrates/ Products (Substrates)
Organic Solvent Stability
Organism
Oxidation Stability
Posttranslational Modification
Purification (Commentary)
Reaction
Renatured (Commentary)
Source Tissue
Specific Activity [micromol/min/mg]
Storage Stability
Substrates and Products (Substrate)
Subunits
Temperature Optimum [°C]
Temperature Range [°C]
Temperature Stability [°C]
Turnover Number [1/s]
pH Optimum
pH Range
pH Stability
Cofactor
Ki Value [mM]
pI Value
IC50 Value
Activating Compound (protein specific)
Application (protein specific)
Cloned(Commentary) (protein specific)
Cofactor (protein specific)
Crystallization (Commentary) (protein specific)
Engineering (protein specific)
General Stability (protein specific)
IC50 Value (protein specific)
Inhibitors (protein specific)
Ki Value [mM] (protein specific)
KM Value [mM] (protein specific)
Localization (protein specific)
Metals/Ions (protein specific)
Molecular Weight [Da] (protein specific)
Natural Substrates/ Products (Substrates) (protein specific)
Organic Solvent Stability (protein specific)
Oxidation Stability (protein specific)
Posttranslational Modification (protein specific)
Purification (Commentary) (protein specific)
Renatured (Commentary) (protein specific)
Source Tissue (protein specific)
Specific Activity [micromol/min/mg] (protein specific)
Storage Stability (protein specific)
Substrates and Products (Substrate) (protein specific)
Subunits (protein specific)
Temperature Optimum [°C] (protein specific)
Temperature Range [°C] (protein specific)
Temperature Stability [°C] (protein specific)
Turnover Number [1/s] (protein specific)
pH Optimum (protein specific)
pH Range (protein specific)
pH Stability (protein specific)
pI Value (protein specific)
Expression
General Information
General Information (protein specific)
Expression (protein specific)
KCat/KM [mM/s]
KCat/KM [mM/s] (protein specific)
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2
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1
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4
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748329
Nilsson
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Arabidopsis thaliana
J. Exp. Bot.
67
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2016
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98
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2016
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747291
Liu
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Amaranthus tricolor
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38
2439-2449
2015
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3
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730040
Brash
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289
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730562
Padilla
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Olea europaea
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102
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729489
Yoeun
Dual positional substrate spec ...
Oryza sativa
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46
151-156
2013
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729734
Toporkova
Structure-function relationshi ...
Linum usitatissimum, Nicotiana tabacum
FEBS Lett.
587
2552-2558
2013
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730012
Hoffmann
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Aspergillus terreus, Aspergillus terreus A1156
J. Biol. Chem.
288
11459-11469
2013
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730087
Bruehlmann
Directed evolution of a 13-hyd ...
Psidium guajava
J. Biotechnol.
163
339-345
2013
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730154
Hoffmann
Discovery of a linoleate 9S-di ...
Fusarium oxysporum, Fusarium oxysporum Fo5176
J. Lipid Res.
54
3471-3480
2013
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730362
Hosur Gnanaprakash
Association between accumulati ...
Cenchrus americanus
Mol. Biol. Rep.
40
6821-6829
2013
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3202
Hamberg
Biosynthesis of 12-oxo-10,15(Z ...
Zea mays
Biochem. Biophys. Res. Commun.
156
543-550
1988
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648481
Hamberg
-
Mechanism of corn hydroperoxid ...
Zea mays
Biochim. Biophys. Acta
920
76-84
1987
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648484
Kermasha
Conversion of linoleic acid hy ...
Phaseolus vulgaris
J. Food Biochem.
10
285-303
1986
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648492
Grossman
-
Purification and partial chara ...
Solanum melongena, Zea mays
Biochim. Biophys. Acta
752
65-72
1983
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7
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648485
Feng
-
Formation of gamma-ketols from ...
Linum usitatissimum
Lipids
16
377-379
1981
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648487
Lulai
Metabolism of linoleic acid by ...
Hordeum vulgare
Plant Physiol.
68
950-955
1981
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4
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648486
Gardner
-
Stereospecificity of linoleic ...
Zea mays
Lipids
14
208-211
1979
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648493
Yabuuchi
-
Partial purification and chara ...
Hordeum vulgare subsp. vulgare
Phytochemistry
15
387-390
1976
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648494
Heimann
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Uber den enzymatischen Hydrope ...
Avena sativa
Helv. Chim. Acta
56
463-469
1973
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