1.14.99.52: L-cysteinyl-L-histidinylsulfoxide synthase
This is an abbreviated version!
For detailed information about L-cysteinyl-L-histidinylsulfoxide synthase, go to the full flat file.
Reaction
Synonyms
5-histidylcysteine sulfoxide synthase, OvoA, OvoA-like protein, OvoAe, OvoAErwin, OvoAt, OvoA_1, OvoA_2, PlOvoA, short OvoA homologue, SpOvoA, sulfoxide synthase
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Substrates Products
Substrates Products on EC 1.14.99.52 - L-cysteinyl-L-histidinylsulfoxide synthase
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REACTION DIAGRAM
2-fluoro-L-histidine + L-cysteine + O2
S-(2-fluoro-L-histidin-5-yl)-L-cysteine S-oxide + H2O
D-histidine + L-cysteine + O2
S-(D-histidin-5-yl)-L-cysteine S-oxide + S-(D-histidin-2-yl)-L-cysteine S-oxide + H2O
hercynine + gamma-L-glutamyl-L-cysteine + O2
gamma-L-glutamyl-S-(hercyn-2-yl)-L-cysteine S-oxide + H2O
histamine + L-cysteine + O2
S-(histamin-5-yl)-L-cysteine S-oxide + H2O
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?
L-histidinamide + L-cysteine + O2
S-(L-histidinamide-5-yl)-L-cysteine S-oxide + H2O
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?
S-(2-fluoro-L-histidin-5-yl)-L-cysteine S-oxide + H2O
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?
2-fluoro-L-histidine + L-cysteine + O2
S-(2-fluoro-L-histidin-5-yl)-L-cysteine S-oxide + H2O
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?
? + H2O
very low activity
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?
4-methylimidazole + L-cysteine + O2
? + H2O
very low activity
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?
S-(D-histidin-5-yl)-L-cysteine S-oxide + S-(D-histidin-2-yl)-L-cysteine S-oxide + H2O
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the reaction product as a mixture of 63% 5-D-histidyl-L-cysteine sulfoxide and 37% 2-D-histidyl-L-cysteine sulfoxide
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?
D-histidine + L-cysteine + O2
S-(D-histidin-5-yl)-L-cysteine S-oxide + S-(D-histidin-2-yl)-L-cysteine S-oxide + H2O
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the reaction product as a mixture of 63% 5-D-histidyl-L-cysteine sulfoxide and 37% 2-D-histidyl-L-cysteine sulfoxide
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?
gamma-L-glutamyl-S-(hercyn-2-yl)-L-cysteine S-oxide + H2O
Moorena producens
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-
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?
hercynine + gamma-L-glutamyl-L-cysteine + O2
gamma-L-glutamyl-S-(hercyn-2-yl)-L-cysteine S-oxide + H2O
Moorena producens PAL-8-15-08-1
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-
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?
S-(hercyn-2-yl)-L-cysteine S-oxide + H2O
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?
hercynine + L-cysteine + O2
S-(hercyn-2-yl)-L-cysteine S-oxide + H2O
-
reaction of EC 1.14.99.51
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-
?
hercynine + L-cysteine + O2
S-(hercyn-2-yl)-L-cysteine S-oxide + H2O
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-
-
?
cysteine sulfinic acid + H2O
oxidation of cysteine to cysteine sulfinic acid in presence of hercynine or L-histidine
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?
L-cysteine + O2
cysteine sulfinic acid + H2O
oxidation of cysteine to cysteine sulfinic acid in presence of hercynine or L-histidine
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?
L-cystine + H2O
oxidation of cysteine to cystine
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?
L-cysteine + O2
L-cystine + H2O
oxidation of cysteine to cystine
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?
S-(L-histidin-5-yl)-L-cysteine S-oxide + H2O
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-
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?
L-histidine + L-cysteine + O2
S-(L-histidin-5-yl)-L-cysteine S-oxide + H2O
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-
-
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?
L-histidine + L-cysteine + O2
S-(L-histidin-5-yl)-L-cysteine S-oxide + H2O
evaluation of the mechanistic feasibility of the various possible iron-oxygen oxidants in the proton-coupled electron transfer process or the electron transfer process, overview
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-
?
L-histidine + L-cysteine + O2
S-(L-histidin-5-yl)-L-cysteine S-oxide + H2O
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OvoA modifies the C5 position of the imidazole ring of L-His, site selectivity of the transformation
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?
L-histidine + L-cysteine + O2
S-(L-histidin-5-yl)-L-cysteine S-oxide + H2O
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-
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?
L-histidine + L-cysteine + O2
S-(L-histidin-5-yl)-L-cysteine S-oxide + H2O
evaluation of the mechanistic feasibility of the various possible iron-oxygen oxidants in the proton-coupled electron transfer process or the electron transfer process, overview
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-
?
L-histidine + L-cysteine + O2
S-(L-histidin-5-yl)-L-cysteine S-oxide + H2O
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?
L-histidine + L-cysteine + O2
S-(L-histidin-5-yl)-L-cysteine S-oxide + H2O
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?
L-histidine + L-cysteine + O2
S-(L-histidin-5-yl)-L-cysteine S-oxide + H2O
Moorena producens
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?
L-histidine + L-cysteine + O2
S-(L-histidin-5-yl)-L-cysteine S-oxide + H2O
Moorena producens PAL-8-15-08-1
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?
L-histidine + L-cysteine + O2
S-(L-histidin-5-yl)-L-cysteine S-oxide + H2O
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?
L-histidine + L-cysteine + O2
S-(L-histidin-5-yl)-L-cysteine S-oxide + H2O
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?
L-histidine + L-cysteine + O2
S-(L-histidin-5-yl)-L-cysteine S-oxide + H2O
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-
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?
?
-
besides catalyzing the four-electron oxidative coupling between histidine and cysteine, enzyme OvoA can also catalyze a direct oxidative coupling between hercynine and cysteine, which can shorten the ergothioneine biosynthetic pathway by two steps. Enzyme OvoA can also catalyze the reaction of egtB between hercynine and gamma-L-glutamyl-L-cysteine, EC 1.14.99.50
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?
additional information
?
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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
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?
additional information
?
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OvoA substrate specificity and substrate binding pocket flexibility, NMR analysis, overview
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?
additional information
?
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the enzyme catalyzes the oxidative coupling between histidine and cysteine. It can also catalyze the oxidative coupling between hercynine and cysteine, yet with a different regioselectivity, NMR spectroscopic product analysis, overview. Enzyme OvoA can also catalyze the oxidation of cysteine to either cysteine sulfinic acid or cystine. OvoA-catalyzed reactions can be systematically modulated by a slight modification of one of its substrates, histidine
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?
additional information
?
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OvoA in ovothiol biosynthesis is a mononuclear non-heme iron enzyme catalyzing the oxidative coupling between L-histidine and L-cysteine. It can also catalyze the oxidative coupling between hercynine and cysteine, yet with a different regioselectivity (cf. Ec 1.14.99.51). OvoA can also catalyze the oxidation of cysteine to either cysteine sulfinic acid or cystine, OvoA has cysteine dioxygenase activity (cf. EC 1.13.11.20). A 3-His catalytic triad is a prerequisite for the cysteine dioxygenase activity
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?
additional information
?
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the ovothiol biosynthetic sulfoxide synthase OvoA from Erwinia tasmaniensis (OvoAErwin) is a promiscuous enzyme. This enzyme is most efficient in making its native product S-(L-histidin-5-yl)-L-cysteine S-oxide, but, when presented with N-alpha-trimethylhistidine as a sulfur acceptor, the enzyme switches product specificity and produces gamma-L-glutamyl-S-(hercyn-2-yl)-L-cysteine S-oxide albeit with significantly lower efficiency
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?
additional information
?
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OvoA incubated with hercynine (the normal substrate for EgtB, EC 1.14.99.50) and cysteine produces primarily cysteine sulfinic acid, the product of cysteine dioxygenase-type chemistry, cf. EC 1.13.11.20
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?
additional information
?
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the OvoA-catalyzed reactions can be systematically modulated by a slight modification of one of its substrates, L-histidine. Substrate specificity of OvoA, detailed overview
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?
additional information
?
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when OvoA's native substrate histidine is replaced by hercynine, OvoA can catalyze a one-step transformation reaction of hercynylcysteine S-oxide synthase, EC 1.14.99.51, resulting in kobs changes by 2fold for hercynine, while Km for cysteine increases from 0.3 mM to 3.19 mM. OvoA preferentially uses histidine and cysteine. OvoA also catalyzes the oxidation of cysteine to cysteine sulfinic acid, EC 1.13.11.20. Enzyme activity determination using : a 1H NMR assay of chemical shift of the imidazole hydrogen atoms
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?
additional information
?
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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
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-
?
additional information
?
-
besides catalyzing the four-electron oxidative coupling between histidine and cysteine, enzyme OvoA can also catalyze a direct oxidative coupling between hercynine and cysteine, which can shorten the ergothioneine biosynthetic pathway by two steps. Enzyme OvoA can also catalyze the reaction of egtB between hercynine and gamma-L-glutamyl-L-cysteine, EC 1.14.99.50
-
-
?
additional information
?
-
OvoA substrate specificity and substrate binding pocket flexibility, NMR analysis, overview
-
-
?
additional information
?
-
the enzyme catalyzes the oxidative coupling between histidine and cysteine. It can also catalyze the oxidative coupling between hercynine and cysteine, yet with a different regioselectivity, NMR spectroscopic product analysis, overview. Enzyme OvoA can also catalyze the oxidation of cysteine to either cysteine sulfinic acid or cystine. OvoA-catalyzed reactions can be systematically modulated by a slight modification of one of its substrates, histidine
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-
?
additional information
?
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short cyanobacterial OvoA-type enzymes may contribute to ergothioneine (EC 1.14.99.51) instead of ovothiol production
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?
additional information
?
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Moorena producens
an OvoA-like protein, full-length OvoA homologue, OvoA_2, is a monofunctional sulfoxide synthase
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?
additional information
?
-
Moorena producens
an OvoA-like protein, full-length OvoA homologue, OvoA_2, is a monofunctional sulfoxide synthase
-
-
?
additional information
?
-
Moorena producens
in a competitive reaction containing 1 mM of each histidine, N-alpha-trimethylhistidine, and cysteine, OvoAErwin produces only S-(L-histidin-5-yl)-L-cysteine S-oxide, whereas OvoAErw-NW and EgtB(ovo) produce exclusively gamma-L-glutamyl-S-(hercyn-2-yl)-L-cysteine S-oxide
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?
additional information
?
-
Moorena producens
in a competitive reaction containing 1 mM of each histidine, N-alpha-trimethylhistidine, and cysteine, OvoAErwin produces only S-(L-histidin-5-yl)-L-cysteine S-oxide, whereas OvoAErw-NW and EgtB(ovo) produce exclusively gamma-L-glutamyl-S-(hercyn-2-yl)-L-cysteine S-oxide
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?
additional information
?
-
Moorena producens PAL-8-15-08-1
an OvoA-like protein, full-length OvoA homologue, OvoA_2, is a monofunctional sulfoxide synthase
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-
?
additional information
?
-
Moorena producens PAL-8-15-08-1
an OvoA-like protein, full-length OvoA homologue, OvoA_2, is a monofunctional sulfoxide synthase
-
-
?
additional information
?
-
Moorena producens PAL-8-15-08-1
in a competitive reaction containing 1 mM of each histidine, N-alpha-trimethylhistidine, and cysteine, OvoAErwin produces only S-(L-histidin-5-yl)-L-cysteine S-oxide, whereas OvoAErw-NW and EgtB(ovo) produce exclusively gamma-L-glutamyl-S-(hercyn-2-yl)-L-cysteine S-oxide
-
-
?
additional information
?
-
Moorena producens PAL-8-15-08-1
in a competitive reaction containing 1 mM of each histidine, N-alpha-trimethylhistidine, and cysteine, OvoAErwin produces only S-(L-histidin-5-yl)-L-cysteine S-oxide, whereas OvoAErw-NW and EgtB(ovo) produce exclusively gamma-L-glutamyl-S-(hercyn-2-yl)-L-cysteine S-oxide
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?