BRENDA - Enzyme Database show

An ancient relative of cyclooxygenase in cyanobacteria is a linoleate 10S-dioxygenase that works in tandem with a catalase-related protein with specific 10S-hydroperoxide lyase activity

Brash, A.R.; Niraula, N.P.; Boeglin, W.E.; Mashhadi, Z.; J. Biol. Chem. 289, 13101-13111 (2014)

Data extracted from this reference:

Cloned(Commentary)
EC Number
Commentary
Organism
1.13.11.77
gene Npun_R5469, sequence comparisons and phylogenetic tree, recombinant expression of His-tagged enzyme in Escherichia coli
Nostoc punctiforme
KM Value [mM]
EC Number
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
1.13.11.77
0.013
-
alpha-linolenate
recombinant enzyme, pH and temperature not specified in the publication
Nostoc punctiforme
1.13.11.77
0.063
-
linoleate
recombinant enzyme, pH and temperature not specified in the publication
Nostoc punctiforme
1.13.11.77
0.113
-
oleate
recombinant enzyme, pH and temperature not specified in the publication
Nostoc punctiforme
Natural Substrates/ Products (Substrates)
EC Number
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
1.13.11.77
alpha-linolenate + O2
Nostoc punctiforme
-
(8E,10S,12Z,15Z)-10-hydroperoxyoctadeca-8,12,15-trienoate
-
-
?
1.13.11.77
linoleate + O2
Nostoc punctiforme
-
(8E,10S,12Z)-10-hydroperoxyoctadeca-8,12-dienoate
-
-
?
1.13.11.77
oleate + O2
Nostoc punctiforme
-
(8E,10S)-10-hydroperoxyoctadeca-8-enoate
-
-
?
Organism
EC Number
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
1.13.11.77
Nostoc punctiforme
B2J5P4
-
-
Purification (Commentary)
EC Number
Commentary
Organism
1.13.11.77
recombinant His-tagged enzyme from Escherichia coli by nickel affinity chromatography
Nostoc punctiforme
Substrates and Products (Substrate)
EC Number
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
1.13.11.77
alpha-linolenate + O2
-
745297
Nostoc punctiforme
(8E,10S,12Z,15Z)-10-hydroperoxyoctadeca-8,12,15-trienoate
-
-
-
?
1.13.11.77
linoleate + O2
-
745297
Nostoc punctiforme
(8E,10S,12Z)-10-hydroperoxyoctadeca-8,12-dienoate
-
-
-
?
1.13.11.77
linoleate + O2
racemic substrate, absolute stereospecific reaction, only formation of 10S product
745297
Nostoc punctiforme
(8E,10S,12Z)-10-hydroperoxyoctadeca-8,12-dienoate
-
-
-
?
1.13.11.77
additional information
enzyme Np-diox is best described as an oleate or linoleate dioxygenase, albeit with alpha-linolenic acid very competitive at low substrate concentrations
745297
Nostoc punctiforme
?
-
-
-
-
1.13.11.77
additional information
racemic 1-octen-3-ol is formed in reaction of linoleate 10S-hydroperoxide with hematin or ferrous ions
745297
Nostoc punctiforme
?
-
-
-
-
1.13.11.77
oleate + O2
-
745297
Nostoc punctiforme
(8E,10S)-10-hydroperoxyoctadeca-8-enoate
-
-
-
?
Turnover Number [1/s]
EC Number
Turnover Number Minimum [1/s]
Turnover Number Maximum [1/s]
Substrate
Commentary
Organism
Structure
1.13.11.77
31
-
alpha-linolenate
recombinant enzyme, pH and temperature not specified in the publication
Nostoc punctiforme
1.13.11.77
135
-
linoleate
recombinant enzyme, pH and temperature not specified in the publication
Nostoc punctiforme
1.13.11.77
178
-
oleate
recombinant enzyme, pH and temperature not specified in the publication
Nostoc punctiforme
Cloned(Commentary) (protein specific)
EC Number
Commentary
Organism
1.13.11.77
gene Npun_R5469, sequence comparisons and phylogenetic tree, recombinant expression of His-tagged enzyme in Escherichia coli
Nostoc punctiforme
KM Value [mM] (protein specific)
EC Number
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
1.13.11.77
0.013
-
alpha-linolenate
recombinant enzyme, pH and temperature not specified in the publication
Nostoc punctiforme
1.13.11.77
0.063
-
linoleate
recombinant enzyme, pH and temperature not specified in the publication
Nostoc punctiforme
1.13.11.77
0.113
-
oleate
recombinant enzyme, pH and temperature not specified in the publication
Nostoc punctiforme
Natural Substrates/ Products (Substrates) (protein specific)
EC Number
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
1.13.11.77
alpha-linolenate + O2
Nostoc punctiforme
-
(8E,10S,12Z,15Z)-10-hydroperoxyoctadeca-8,12,15-trienoate
-
-
?
1.13.11.77
linoleate + O2
Nostoc punctiforme
-
(8E,10S,12Z)-10-hydroperoxyoctadeca-8,12-dienoate
-
-
?
1.13.11.77
oleate + O2
Nostoc punctiforme
-
(8E,10S)-10-hydroperoxyoctadeca-8-enoate
-
-
?
Purification (Commentary) (protein specific)
EC Number
Commentary
Organism
1.13.11.77
recombinant His-tagged enzyme from Escherichia coli by nickel affinity chromatography
Nostoc punctiforme
Substrates and Products (Substrate) (protein specific)
EC Number
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
1.13.11.77
alpha-linolenate + O2
-
745297
Nostoc punctiforme
(8E,10S,12Z,15Z)-10-hydroperoxyoctadeca-8,12,15-trienoate
-
-
-
?
1.13.11.77
linoleate + O2
-
745297
Nostoc punctiforme
(8E,10S,12Z)-10-hydroperoxyoctadeca-8,12-dienoate
-
-
-
?
1.13.11.77
linoleate + O2
racemic substrate, absolute stereospecific reaction, only formation of 10S product
745297
Nostoc punctiforme
(8E,10S,12Z)-10-hydroperoxyoctadeca-8,12-dienoate
-
-
-
?
1.13.11.77
additional information
enzyme Np-diox is best described as an oleate or linoleate dioxygenase, albeit with alpha-linolenic acid very competitive at low substrate concentrations
745297
Nostoc punctiforme
?
-
-
-
-
1.13.11.77
additional information
racemic 1-octen-3-ol is formed in reaction of linoleate 10S-hydroperoxide with hematin or ferrous ions
745297
Nostoc punctiforme
?
-
-
-
-
1.13.11.77
oleate + O2
-
745297
Nostoc punctiforme
(8E,10S)-10-hydroperoxyoctadeca-8-enoate
-
-
-
?
Turnover Number [1/s] (protein specific)
EC Number
Turnover Number Minimum [1/s]
Turnover Number Maximum [1/s]
Substrate
Commentary
Organism
Structure
1.13.11.77
31
-
alpha-linolenate
recombinant enzyme, pH and temperature not specified in the publication
Nostoc punctiforme
1.13.11.77
135
-
linoleate
recombinant enzyme, pH and temperature not specified in the publication
Nostoc punctiforme
1.13.11.77
178
-
oleate
recombinant enzyme, pH and temperature not specified in the publication
Nostoc punctiforme
General Information
EC Number
General Information
Commentary
Organism
1.13.11.77
evolution
linoleate 10S-dioxygenase is an ancient relative of cyclooxygenase in cyanobacteria, linoleate 10S-dioxygenase works in tandem with a catalase-related protein with specific 10S-hydroperoxide lyase activity. Neighboring cyanobacterial genes, dioxygenase and catalase, are identified as linoleate 10S-dioxygenase and 10Shydroperoxide lyase, respectively. The Nostoc linoleate 10S-dioxygenase, the sequence of which contains the signature catalytic sequence of cyclooxygenases and fungal linoleate dioxygenases (YRWH), appears to be a heme dioxygenase ancestor
Nostoc punctiforme
1.13.11.77
metabolism
the immediate downstream gene, Np-cat, encodes a specific linoleate 10S-hydroperoxide lyase (10S-hydroperoxyoleate being metabolized at only 3% of the rate) converting the product of Np-diox and working in tandem with it
Nostoc punctiforme
1.13.11.77
physiological function
enzyme Np-diox is an oleate and linoleate heme 10S-dioxygenase-alpha-linolenate is also efficiently metabolized at lower concentrations, but it much more rapidly leads to enzyme inactivation
Nostoc punctiforme
General Information (protein specific)
EC Number
General Information
Commentary
Organism
1.13.11.77
evolution
linoleate 10S-dioxygenase is an ancient relative of cyclooxygenase in cyanobacteria, linoleate 10S-dioxygenase works in tandem with a catalase-related protein with specific 10S-hydroperoxide lyase activity. Neighboring cyanobacterial genes, dioxygenase and catalase, are identified as linoleate 10S-dioxygenase and 10Shydroperoxide lyase, respectively. The Nostoc linoleate 10S-dioxygenase, the sequence of which contains the signature catalytic sequence of cyclooxygenases and fungal linoleate dioxygenases (YRWH), appears to be a heme dioxygenase ancestor
Nostoc punctiforme
1.13.11.77
metabolism
the immediate downstream gene, Np-cat, encodes a specific linoleate 10S-hydroperoxide lyase (10S-hydroperoxyoleate being metabolized at only 3% of the rate) converting the product of Np-diox and working in tandem with it
Nostoc punctiforme
1.13.11.77
physiological function
enzyme Np-diox is an oleate and linoleate heme 10S-dioxygenase-alpha-linolenate is also efficiently metabolized at lower concentrations, but it much more rapidly leads to enzyme inactivation
Nostoc punctiforme
KCat/KM [mM/s]
EC Number
kcat/KM Value [1/mMs-1]
kcat/KM Value Maximum [1/mMs-1]
Substrate
Commentary
Organism
Structure
1.13.11.77
1600
-
oleate
recombinant enzyme, pH and temperature not specified in the publication
Nostoc punctiforme
1.13.11.77
2100
-
linoleate
recombinant enzyme, pH and temperature not specified in the publication
Nostoc punctiforme
1.13.11.77
2400
-
alpha-linolenate
recombinant enzyme, pH and temperature not specified in the publication
Nostoc punctiforme
KCat/KM [mM/s] (protein specific)
EC Number
KCat/KM Value [1/mMs-1]
KCat/KM Value Maximum [1/mMs-1]
Substrate
Commentary
Organism
Structure
1.13.11.77
1600
-
oleate
recombinant enzyme, pH and temperature not specified in the publication
Nostoc punctiforme
1.13.11.77
2100
-
linoleate
recombinant enzyme, pH and temperature not specified in the publication
Nostoc punctiforme
1.13.11.77
2400
-
alpha-linolenate
recombinant enzyme, pH and temperature not specified in the publication
Nostoc punctiforme