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Synonyms: CYP158A2 (gene name), cytochrome P450 158A2

Systematic Name: flaviolin,reduced ferredoxin:oxygen oxidoreductase

Unification Links: BRENDA:1.14.19.69, ENZYME:1.14.19.69, IUBMB-ExplorEnz:1.14.19.69

Supersedes EC number: 1.14.21.7

Reaction:
2 flaviolin + 2 reduced ferredoxin [iron-sulfur] cluster + dioxygen + 2 H⁺ → 3,8'-biflaviolin + 2 oxidized ferredoxin [iron-sulfur] cluster + 2 H₂O,
2 flaviolin + 2 reduced ferredoxin [iron-sulfur] cluster + dioxygen + 2 H⁺ → 3,3'-biflaviolin + 2 oxidized ferredoxin [iron-sulfur] cluster + 2 H₂O

Enzymes and Genes:
biflaviolin synthase: CYP158A1 ( Streptomyces coelicolor A3(2) )
biflaviolin synthase: CYP158A2 ( Streptomyces coelicolor A3(2) )

Summary:
This cytochrome-P450 (heme-thiolate) enzyme, from the soil-dwelling bacterium Streptomyces coelicolor A3(2), catalyses a phenol oxidation C-C coupling reaction, which results in the polymerization of flaviolin to form biflaviolin or triflaviolin without the incorporation of oxygen into the product [Zhao05, Zhao07a]. The products are highly conjugated pigments that protect the bacterium from the deleterious effects of UV irradiation [Zhao05].

Citations: [Zhao05a]

References

Zhao05: Zhao B, Guengerich FP, Bellamine A, Lamb DC, Izumikawa M, Lei L, Podust LM, Sundaramoorthy M, Kalaitzis JA, Reddy LM, Kelly SL, Moore BS, Stec D, Voehler M, Falck JR, Shimada T, Waterman MR (2005). "Binding of two flaviolin substrate molecules, oxidative coupling, and crystal structure of Streptomyces coelicolor A3(2) cytochrome P450 158A2." J Biol Chem 280(12);11599-607. PMID: 15659395

Zhao05a: Zhao B, Guengerich FP, Voehler M, Waterman MR (2005). "Role of active site water molecules and substrate hydroxyl groups in oxygen activation by cytochrome P450 158A2: a new mechanism of proton transfer." J Biol Chem 280(51);42188-97. PMID: 16239228

Zhao07a: Zhao B, Lamb DC, Lei L, Kelly SL, Yuan H, Hachey DL, Waterman MR (2007). "Different binding modes of two flaviolin substrate molecules in cytochrome P450 158A1 (CYP158A1) compared to CYP158A2." Biochemistry 46(30);8725-33. PMID: 17614370