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Literature summary extracted from

  • Braunshausen, A.; Seebeck, F.P.
    Identification and characterization of the first ovothiol biosynthetic enzyme (2011), J. Am. Chem. Soc., 133, 1757-1759.
    View publication on PubMed

Cloned(Commentary)

EC Number Cloned (Comment) Organism
1.14.99.52 gene ovoA, recombinant expression of His-tagged enzyme in Escherichia coli Trypanosoma cruzi
1.14.99.52 gene ovoA, recombinant expression of His-tagged enzyme in Escherichia coli Erwinia tasmaniensis

Protein Variants

EC Number Protein Variants Comment Organism
1.14.99.52 E176A site-directed mutagenesis, the mutant shows reduced enzyme activity by at least 100fold compared to the wild-type enzyme Erwinia tasmaniensis
1.14.99.52 H170A site-directed mutagenesis, the mutant shows reduced enzyme activity by at least 100fold compared to the wild-type enzyme Erwinia tasmaniensis
1.14.99.52 H174A site-directed mutagenesis, the mutant shows reduced enzyme activity by at least 100fold compared to the wild-type enzyme Erwinia tasmaniensis

Metals/Ions

EC Number Metals/Ions Comment Organism Structure
1.14.99.52 Fe2+ a mononuclear non-heme iron enzyme, iron-dependent enzyme, the molecular basis for iron recognition probably maps to a conserved HX3HXE motif in the N-terminal domains of both OvoA Trypanosoma cruzi
1.14.99.52 Fe2+ a mononuclear non-heme iron enzyme, iron-dependent enzyme, the molecular basis for iron recognition probably maps to a conserved HX3HXE motif in the N-terminal domains of both OvoA Erwinia tasmaniensis

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.14.99.52 L-histidine + L-cysteine + O2 Trypanosoma cruzi
-
 S-(L-histidin-5-yl)-L-cysteine S-oxide + H2O
-
 ?
1.14.99.52 L-histidine + L-cysteine + O2 Erwinia tasmaniensis
-
 S-(L-histidin-5-yl)-L-cysteine S-oxide + H2O
-
 ?
1.14.99.52 L-histidine + L-cysteine + O2 Erwinia tasmaniensis DSM 17950
-
 S-(L-histidin-5-yl)-L-cysteine S-oxide + H2O
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
1.14.99.52 Erwinia tasmaniensis B2VFD8 gene ovoA
-
1.14.99.52 Erwinia tasmaniensis DSM 17950 B2VFD8 gene ovoA
-
1.14.99.52 Trypanosoma cruzi
-
-
-

Purification (Commentary)

EC Number Purification (Comment) Organism
1.14.99.52 recombinant His-tagged enzyme from Escherichia coli by nickel affinity chromatography Trypanosoma cruzi
1.14.99.52 recombinant His-tagged enzyme from Escherichia coli by nickel affinity chromatography Erwinia tasmaniensis

Reaction

EC Number Reaction Comment Organism Reaction ID
1.14.99.52 L-histidine + L-cysteine + O2 = S-(L-histidin-5-yl)-L-cysteine S-oxide + H2O catalytic mechanism: C-S bond formation is initiated by formation of a histidyl sp2 radical, formation of a histidyl PI-radical, and electrophilic attack of the iron-coordinated cysteine sulfoxide on histidine. The enzyme OvoA oxidizes cysteine to access an iron(IV)-oxo state (a in Figure 2) which then mediates oxidative sulfurization of histidine Erwinia tasmaniensis
a
1.14.99.52 L-histidine + L-cysteine + O2 = S-(L-histidin-5-yl)-L-cysteine S-oxide + H2O catalytic mechanism: C-S bond formation is initiated by formation of a histidyl sp2 radical, formation of a histidyl PI-radical, and electrophilic attack of the iron-coordinated cysteine sulfoxide on histidine. The enzyme OvoA oxidizes cysteine to access an iron(IV)-oxo state which then mediates oxidative sulfurization of histidine Trypanosoma cruzi
a

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.14.99.52 L-histidine + L-cysteine + O2
-
 Trypanosoma cruzi S-(L-histidin-5-yl)-L-cysteine S-oxide + H2O
-
 ?
1.14.99.52 L-histidine + L-cysteine + O2
-
 Erwinia tasmaniensis S-(L-histidin-5-yl)-L-cysteine S-oxide + H2O
-
 ?
1.14.99.52 L-histidine + L-cysteine + O2
-
 Erwinia tasmaniensis DSM 17950 S-(L-histidin-5-yl)-L-cysteine S-oxide + H2O
-
 ?

Synonyms

EC Number Synonyms Comment Organism
1.14.99.52 5-histidylcysteine sulfoxide synthase
-
 Trypanosoma cruzi
1.14.99.52 5-histidylcysteine sulfoxide synthase
-
 Erwinia tasmaniensis
1.14.99.52 OvoA
-
 Trypanosoma cruzi
1.14.99.52 OvoA
-
 Erwinia tasmaniensis
1.14.99.52 OvoAe
-
 Erwinia tasmaniensis
1.14.99.52 OvoAt
-
 Trypanosoma cruzi

General Information

EC Number General Information Comment Organism
1.14.99.52 metabolism the enzyme is involved in the ovothiol biosynthesis Trypanosoma cruzi
1.14.99.52 metabolism the enzyme is involved in the ovothiol biosynthesis Erwinia tasmaniensis
1.14.99.52 additional information the enzyme requires coordination of iron(II) to an unusual iron-binding motif Trypanosoma cruzi
1.14.99.52 additional information the enzyme requires coordination of iron(II) to an unusual iron-binding motif Erwinia tasmaniensis
1.14.99.52 physiological function the enzyme is the ovothiol biosynthetic enzyme, ovothiols are histidine-derived thiols Trypanosoma cruzi
1.14.99.52 physiological function the enzyme is the ovothiol biosynthetic enzyme, ovothiols are histidine-derived thiols Erwinia tasmaniensis