BRENDA - Enzyme Database show
show all sequences of 1.14.99.52

Substrate specificity of an oxygen dependent sulfoxide synthase in ovothiol biosynthesis

Mashabela, G.T.; Seebeck, F.P.; Chem. Commun. (Camb. ) 49, 7714-7716 (2013)

Data extracted from this reference:

Activating Compound
Activating Compound
Commentary
Organism
Structure
ascorbate
provides a nearly 100fold increase in enzyme activity
Erwinia tasmaniensis
D-isoascorbate
provides a nearly 100fold increase in enzyme activity
Erwinia tasmaniensis
KM Value [mM]
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
0.23
-
histamine
pH 8.0, 26C
Erwinia tasmaniensis
0.31
-
L-histidinamide
pH 8.0, 26C
Erwinia tasmaniensis
0.34
-
L-histidine
pH 8.0, 26C
Erwinia tasmaniensis
0.35
-
L-cysteine
pH 8.0, 26C, with L-histidine
Erwinia tasmaniensis
0.67
-
D-histidine
pH 8.0, 26C
Erwinia tasmaniensis
Localization
Localization
Commentary
Organism
GeneOntology No.
Textmining
membrane
-
Erwinia tasmaniensis
16020
-
Metals/Ions
Metals/Ions
Commentary
Organism
Structure
Fe2+
dependent on
Erwinia tasmaniensis
Natural Substrates/ Products (Substrates)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
L-histidine + L-cysteine + O2
Erwinia tasmaniensis
-
S-(L-histidin-5-yl)-L-cysteine S-oxide + H2O
-
-
?
L-histidine + L-cysteine + O2
Erwinia tasmaniensis DSM 17950
-
S-(L-histidin-5-yl)-L-cysteine S-oxide + H2O
-
-
?
Organism
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
Erwinia tasmaniensis
B2VFD8
gene ovoA
-
Erwinia tasmaniensis DSM 17950
B2VFD8
gene ovoA
-
Reaction
Reaction
Commentary
Organism
L-histidine + L-cysteine + O2 = S-(L-histidin-5-yl)-L-cysteine S-oxide + H2O
the enzyme catalysis follows an thiol-ene type mechanism, it catalyzes C-S bond formation through an OvoA generated L-cysteine thiyl radical that attacks the unsaturated imidazole ring of L-histidine, overview
Erwinia tasmaniensis
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
2-fluoro-L-histidine + L-cysteine + O2
-
733647
Erwinia tasmaniensis
S-(2-fluoro-L-histidin-5-yl)-L-cysteine S-oxide + H2O
-
-
-
?
2-fluoro-L-histidine + L-cysteine + O2
-
733647
Erwinia tasmaniensis DSM 17950
S-(2-fluoro-L-histidin-5-yl)-L-cysteine S-oxide + H2O
-
-
-
?
4-methylimidazole + L-cysteine + O2
very low activity
733647
Erwinia tasmaniensis
? + H2O
-
-
-
?
4-methylimidazole + L-cysteine + O2
very low activity
733647
Erwinia tasmaniensis DSM 17950
? + H2O
-
-
-
?
D-histidine + L-cysteine + O2
-
733647
Erwinia tasmaniensis
S-(D-histidin-5-yl)-L-cysteine S-oxide + S-(D-histidin-2-yl)-L-cysteine S-oxide + H2O
the reaction product as a mixture of 63% 5-D-histidyl-L-cysteine sulfoxide and 37% 2-D-histidyl-L-cysteine sulfoxide
-
-
?
D-histidine + L-cysteine + O2
-
733647
Erwinia tasmaniensis DSM 17950
S-(D-histidin-5-yl)-L-cysteine S-oxide + S-(D-histidin-2-yl)-L-cysteine S-oxide + H2O
the reaction product as a mixture of 63% 5-D-histidyl-L-cysteine sulfoxide and 37% 2-D-histidyl-L-cysteine sulfoxide
-
-
?
histamine + L-cysteine + O2
-
733647
Erwinia tasmaniensis
S-(histamin-5-yl)-L-cysteine S-oxide + H2O
-
-
-
?
L-histidinamide + L-cysteine + O2
-
733647
Erwinia tasmaniensis
S-(L-histidinamide-5-yl)-L-cysteine S-oxide + H2O
-
-
-
?
L-histidine + L-cysteine + O2
-
733647
Erwinia tasmaniensis
S-(L-histidin-5-yl)-L-cysteine S-oxide + H2O
-
-
-
?
L-histidine + L-cysteine + O2
-
733647
Erwinia tasmaniensis DSM 17950
S-(L-histidin-5-yl)-L-cysteine S-oxide + H2O
-
-
-
?
additional information
OvoA catalyzes efficient in vitro sulfurization of L-histidine, D-histidine, 2-fluoro-L-histidine and compounds other than amino acids. No activity with 4-bromoimidazole, 4(5)-(hydroxymethyl) imidazole, urocanic acid, N-alpha-acetyl-L-histidine, and carnosine, as well as 3-pyridin-2-ylalanine, 3-pyridin-3-ylalanine, 3-(2-thioxo-2,3-dihydro-1H-imidazol-4-yl)-L-alaninamide, 1-methylimidazole, 2,5-diiodo-L-histidine, 5-fluoro-L-histidine, 5-chloro-L-histidine, 5-bromo-L-histidine, and 5-iodo-L-histidine
733647
Erwinia tasmaniensis
?
-
-
-
-
additional information
OvoA catalyzes efficient in vitro sulfurization of L-histidine, D-histidine, 2-fluoro-L-histidine and compounds other than amino acids. No activity with 4-bromoimidazole, 4(5)-(hydroxymethyl) imidazole, urocanic acid, N-alpha-acetyl-L-histidine, and carnosine, as well as 3-pyridin-2-ylalanine, 3-pyridin-3-ylalanine, 3-(2-thioxo-2,3-dihydro-1H-imidazol-4-yl)-L-alaninamide, 1-methylimidazole, 2,5-diiodo-L-histidine, 5-fluoro-L-histidine, 5-chloro-L-histidine, 5-bromo-L-histidine, and 5-iodo-L-histidine
733647
Erwinia tasmaniensis DSM 17950
?
-
-
-
-
Temperature Optimum [C]
Temperature Optimum [C]
Temperature Optimum Maximum [C]
Commentary
Organism
26
-
assay at
Erwinia tasmaniensis
Turnover Number [1/s]
Turnover Number Minimum [1/s]
Turnover Number Maximum [1/s]
Substrate
Commentary
Organism
Structure
0.36
-
histamine
pH 8.0, 26C
Erwinia tasmaniensis
0.57
-
L-histidinamide
pH 8.0, 26C
Erwinia tasmaniensis
0.78
-
D-histidine
pH 8.0, 26C
Erwinia tasmaniensis
3.3
-
L-cysteine
pH 8.0, 26C, with L-histidine
Erwinia tasmaniensis
3.4
-
L-histidine
pH 8.0, 26C
Erwinia tasmaniensis
pH Optimum
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
8
-
assay at
Erwinia tasmaniensis
Activating Compound (protein specific)
Activating Compound
Commentary
Organism
Structure
ascorbate
provides a nearly 100fold increase in enzyme activity
Erwinia tasmaniensis
D-isoascorbate
provides a nearly 100fold increase in enzyme activity
Erwinia tasmaniensis
KM Value [mM] (protein specific)
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
0.23
-
histamine
pH 8.0, 26C
Erwinia tasmaniensis
0.31
-
L-histidinamide
pH 8.0, 26C
Erwinia tasmaniensis
0.34
-
L-histidine
pH 8.0, 26C
Erwinia tasmaniensis
0.35
-
L-cysteine
pH 8.0, 26C, with L-histidine
Erwinia tasmaniensis
0.67
-
D-histidine
pH 8.0, 26C
Erwinia tasmaniensis
Localization (protein specific)
Localization
Commentary
Organism
GeneOntology No.
Textmining
membrane
-
Erwinia tasmaniensis
16020
-
Metals/Ions (protein specific)
Metals/Ions
Commentary
Organism
Structure
Fe2+
dependent on
Erwinia tasmaniensis
Natural Substrates/ Products (Substrates) (protein specific)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
L-histidine + L-cysteine + O2
Erwinia tasmaniensis
-
S-(L-histidin-5-yl)-L-cysteine S-oxide + H2O
-
-
?
L-histidine + L-cysteine + O2
Erwinia tasmaniensis DSM 17950
-
S-(L-histidin-5-yl)-L-cysteine S-oxide + H2O
-
-
?
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
2-fluoro-L-histidine + L-cysteine + O2
-
733647
Erwinia tasmaniensis
S-(2-fluoro-L-histidin-5-yl)-L-cysteine S-oxide + H2O
-
-
-
?
2-fluoro-L-histidine + L-cysteine + O2
-
733647
Erwinia tasmaniensis DSM 17950
S-(2-fluoro-L-histidin-5-yl)-L-cysteine S-oxide + H2O
-
-
-
?
4-methylimidazole + L-cysteine + O2
very low activity
733647
Erwinia tasmaniensis
? + H2O
-
-
-
?
4-methylimidazole + L-cysteine + O2
very low activity
733647
Erwinia tasmaniensis DSM 17950
? + H2O
-
-
-
?
D-histidine + L-cysteine + O2
-
733647
Erwinia tasmaniensis
S-(D-histidin-5-yl)-L-cysteine S-oxide + S-(D-histidin-2-yl)-L-cysteine S-oxide + H2O
the reaction product as a mixture of 63% 5-D-histidyl-L-cysteine sulfoxide and 37% 2-D-histidyl-L-cysteine sulfoxide
-
-
?
D-histidine + L-cysteine + O2
-
733647
Erwinia tasmaniensis DSM 17950
S-(D-histidin-5-yl)-L-cysteine S-oxide + S-(D-histidin-2-yl)-L-cysteine S-oxide + H2O
the reaction product as a mixture of 63% 5-D-histidyl-L-cysteine sulfoxide and 37% 2-D-histidyl-L-cysteine sulfoxide
-
-
?
histamine + L-cysteine + O2
-
733647
Erwinia tasmaniensis
S-(histamin-5-yl)-L-cysteine S-oxide + H2O
-
-
-
?
L-histidinamide + L-cysteine + O2
-
733647
Erwinia tasmaniensis
S-(L-histidinamide-5-yl)-L-cysteine S-oxide + H2O
-
-
-
?
L-histidine + L-cysteine + O2
-
733647
Erwinia tasmaniensis
S-(L-histidin-5-yl)-L-cysteine S-oxide + H2O
-
-
-
?
L-histidine + L-cysteine + O2
-
733647
Erwinia tasmaniensis DSM 17950
S-(L-histidin-5-yl)-L-cysteine S-oxide + H2O
-
-
-
?
additional information
OvoA catalyzes efficient in vitro sulfurization of L-histidine, D-histidine, 2-fluoro-L-histidine and compounds other than amino acids. No activity with 4-bromoimidazole, 4(5)-(hydroxymethyl) imidazole, urocanic acid, N-alpha-acetyl-L-histidine, and carnosine, as well as 3-pyridin-2-ylalanine, 3-pyridin-3-ylalanine, 3-(2-thioxo-2,3-dihydro-1H-imidazol-4-yl)-L-alaninamide, 1-methylimidazole, 2,5-diiodo-L-histidine, 5-fluoro-L-histidine, 5-chloro-L-histidine, 5-bromo-L-histidine, and 5-iodo-L-histidine
733647
Erwinia tasmaniensis
?
-
-
-
-
additional information
OvoA catalyzes efficient in vitro sulfurization of L-histidine, D-histidine, 2-fluoro-L-histidine and compounds other than amino acids. No activity with 4-bromoimidazole, 4(5)-(hydroxymethyl) imidazole, urocanic acid, N-alpha-acetyl-L-histidine, and carnosine, as well as 3-pyridin-2-ylalanine, 3-pyridin-3-ylalanine, 3-(2-thioxo-2,3-dihydro-1H-imidazol-4-yl)-L-alaninamide, 1-methylimidazole, 2,5-diiodo-L-histidine, 5-fluoro-L-histidine, 5-chloro-L-histidine, 5-bromo-L-histidine, and 5-iodo-L-histidine
733647
Erwinia tasmaniensis DSM 17950
?
-
-
-
-
Temperature Optimum [C] (protein specific)
Temperature Optimum [C]
Temperature Optimum Maximum [C]
Commentary
Organism
26
-
assay at
Erwinia tasmaniensis
Turnover Number [1/s] (protein specific)
Turnover Number Minimum [1/s]
Turnover Number Maximum [1/s]
Substrate
Commentary
Organism
Structure
0.36
-
histamine
pH 8.0, 26C
Erwinia tasmaniensis
0.57
-
L-histidinamide
pH 8.0, 26C
Erwinia tasmaniensis
0.78
-
D-histidine
pH 8.0, 26C
Erwinia tasmaniensis
3.3
-
L-cysteine
pH 8.0, 26C, with L-histidine
Erwinia tasmaniensis
3.4
-
L-histidine
pH 8.0, 26C
Erwinia tasmaniensis
pH Optimum (protein specific)
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
8
-
assay at
Erwinia tasmaniensis
General Information
General Information
Commentary
Organism
evolution
the enzyme belongs to the sulfoxide synthases
Erwinia tasmaniensis
metabolism
OvoA is an iron(II) dependent sulfoxide synthase which catalyzes the first step in ovothiol A biosynthesis
Erwinia tasmaniensis
General Information (protein specific)
General Information
Commentary
Organism
evolution
the enzyme belongs to the sulfoxide synthases
Erwinia tasmaniensis
metabolism
OvoA is an iron(II) dependent sulfoxide synthase which catalyzes the first step in ovothiol A biosynthesis
Erwinia tasmaniensis
KCat/KM [mM/s]
kcat/KM Value [1/mMs-1]
kcat/KM Value Maximum [1/mMs-1]
Substrate
Commentary
Organism
Structure
0.018
-
4-methylimidazole
pH 8.0, 26C
Erwinia tasmaniensis
1.2
-
D-histidine
pH 8.0, 26C
Erwinia tasmaniensis
1.6
-
histamine
pH 8.0, 26C
Erwinia tasmaniensis
1.8
-
L-histidinamide
pH 8.0, 26C
Erwinia tasmaniensis
9.43
-
L-cysteine
pH 8.0, 26C, with L-histidine
Erwinia tasmaniensis
10
-
L-histidine
pH 8.0, 26C
Erwinia tasmaniensis
KCat/KM [mM/s] (protein specific)
KCat/KM Value [1/mMs-1]
KCat/KM Value Maximum [1/mMs-1]
Substrate
Commentary
Organism
Structure
0.018
-
4-methylimidazole
pH 8.0, 26C
Erwinia tasmaniensis
1.2
-
D-histidine
pH 8.0, 26C
Erwinia tasmaniensis
1.6
-
histamine
pH 8.0, 26C
Erwinia tasmaniensis
1.8
-
L-histidinamide
pH 8.0, 26C
Erwinia tasmaniensis
9.43
-
L-cysteine
pH 8.0, 26C, with L-histidine
Erwinia tasmaniensis
10
-
L-histidine
pH 8.0, 26C
Erwinia tasmaniensis
Other publictions for EC 1.14.99.52
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)
744709
Liao
Convergent evolution of ergot ...
Erwinia tasmaniensis, Microcystis aeruginosa, Moorea producens, Moorea producens PAL-8-15-08-1
ChemBioChem
18
2115-2118
2017
-
-
-
-
-
-
-
-
-
3
-
8
-
6
-
-
-
-
-
-
-
-
12
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
4
-
8
-
-
-
-
-
-
-
-
12
-
-
-
-
-
-
-
-
-
-
7
10
-
-
-
745390
Peck
Go it alone four-electron oxi ...
Erwinia tasmaniensis
J. Biol. Inorg. Chem.
22
381-394
2017
-
-
-
-
-
-
-
-
-
1
-
1
-
1
-
-
-
-
-
-
-
-
3
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
1
-
-
-
-
-
-
-
-
3
-
-
-
-
-
-
-
-
-
-
2
2
-
-
-
746445
Castellano
Shedding light on ovothiol bi ...
Paracentrotus lividus
Sci. Rep.
6
21056
2016
-
-
1
-
-
-
-
-
-
1
-
1
-
6
-
-
-
-
-
3
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
1
-
1
-
-
-
-
-
3
-
-
1
-
-
-
-
-
-
-
-
-
2
4
4
2
-
-
746446
Castellano
Shedding light on ovothiol bi ...
Strongylocentrotus purpuratus
Sci. Rep.
6
21506
2016
-
-
1
-
-
-
-
-
-
-
-
1
-
6
-
-
-
-
-
3
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
3
-
-
1
-
-
-
-
-
-
-
-
-
1
2
2
1
-
-
734828
Song
Cysteine oxidation reactions c ...
Erwinia tasmaniensis, Erwinia tasmaniensis DSM 17950
Org. Lett.
16
2122-2125
2014
-
1
1
-
1
-
-
-
-
1
-
2
-
6
-
-
-
-
-
-
-
-
10
-
-
-
-
-
-
-
-
-
-
-
-
-
1
1
-
-
1
-
-
-
-
-
-
1
-
2
-
-
-
-
-
-
-
-
10
-
-
-
-
-
-
-
-
-
-
3
3
-
-
-
743388
Hu
Bioinformatic and biochemical ...
Erwinia tasmaniensis
Org. Lett.
16
5382-5385
2014
-
1
-
-
-
-
-
-
-
1
-
2
-
1
-
-
-
-
-
-
-
-
3
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
1
-
2
-
-
-
-
-
-
-
-
3
-
-
-
-
-
-
-
-
-
-
2
2
-
-
-
745960
Song
Cysteine oxidation reactions ...
Erwinia tasmaniensis
Org. Lett.
16
2122-2125
2014
-
-
-
-
1
-
-
-
-
1
-
3
-
1
-
-
-
-
-
-
-
-
4
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
1
-
3
-
-
-
-
-
-
-
-
4
-
-
-
-
-
-
-
-
-
-
2
2
-
-
-
733647
Mashabela
Substrate specificity of an ox ...
Erwinia tasmaniensis, Erwinia tasmaniensis DSM 17950
Chem. Commun. (Camb. )
49
7714-7716
2013
2
-
-
-
-
-
-
5
1
1
-
2
-
6
-
-
-
1
-
-
-
-
12
-
1
-
-
5
1
-
-
-
-
-
-
2
-
-
-
-
-
-
-
-
-
5
1
1
-
2
-
-
-
-
-
-
-
-
12
-
1
-
-
5
1
-
-
-
-
2
2
-
6
6
734827
Song
Regioselectivity of the oxidat ...
Erwinia tasmaniensis, Erwinia tasmaniensis DSM 17950
Org. Lett.
15
4854-4857
2013
-
-
1
-
-
-
-
-
-
1
-
6
-
6
-
-
1
-
-
-
-
-
8
-
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
1
-
6
-
-
-
1
-
-
-
-
8
-
-
-
-
-
-
-
-
-
-
3
3
-
-
-
733972
Bushnell
Model iron-oxo species and the ...
Erwinia tasmaniensis, Erwinia tasmaniensis DSM 17950
Inorg. Chem.
51
13351-13356
2012
-
-
-
-
-
-
-
1
-
1
-
2
-
6
-
-
-
1
-
-
-
-
4
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
1
-
2
-
-
-
-
-
-
-
-
4
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
734024
Braunshausen
Identification and characteriz ...
Erwinia tasmaniensis, Erwinia tasmaniensis DSM 17950, Trypanosoma cruzi
J. Am. Chem. Soc.
133
1757-1759
2011
-
-
2
-
3
-
-
-
-
2
-
3
-
7
-
-
2
2
-
-
-
-
3
-
-
-
-
-
-
-
-
-
-
-
-
-
-
2
-
-
3
-
-
-
-
-
-
2
-
3
-
-
-
2
-
-
-
-
3
-
-
-
-
-
-
-
-
-
-
6
6
-
-
-