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Literature summary extracted from

  • Wang, Y.; Chen, H.; Makino, M.; Shiro, Y.; Nagano, S.; Asamizu, S.; Onaka, H.; Shaik, S.
    Theoretical and experimental studies of the conversion of chromopyrrolic acid to an antitumor derivative by cytochrome P450 StaP: the catalytic role of water molecules (2009), J. Am. Chem. Soc., 131, 6748-6762.
    View publication on PubMed

Protein Variants

EC Number Protein Variants Comment Organism
1.13.12.17 H250A the amount of the catalytic product K252c decreases to 25% Streptomyces longisporoflavus
1.13.12.17 H250F the amount of the catalytic product K252c decreases to 72% Streptomyces longisporoflavus

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.13.12.17 dichlorochromopyrrolate + 4 O2 + 4 NADH + 4 H+ Streptomyces longisporoflavus chromopyrrolic acid oxidation by cytochrome P450 StaP is a key process in the biosynthesis of antitumor drugs dichloroarcyriaflavin A + 2 CO2 + 6 H2O + 4 NAD+
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Organism

EC Number Organism UniProt Comment Textmining
1.13.12.17 Streptomyces longisporoflavus
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Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.13.12.17 dichlorochromopyrrolate + 4 O2 + 4 NADH + 4 H+ chromopyrrolic acid oxidation by cytochrome P450 StaP is a key process in the biosynthesis of antitumor drugs Streptomyces longisporoflavus dichloroarcyriaflavin A + 2 CO2 + 6 H2O + 4 NAD+
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 ?
1.13.12.17 dichlorochromopyrrolate + 4 O2 + 4 NADH + 4 H+ the hydrogen-bonding machinery of the pocket deprotonates the carboxylic acid groups of chromopyrrolic acid, while the nearby His250 residue and the crystal waters, Wat644 and Wat789, assist the doubly deprotonated chromopyrrolic acid to transfer electron density to compound I. Hence, chromopyrrolic acid is activated toward proton-coupled electron transfer that sets the entire mechanism in motion. The ensuing mechanism involves a step of C-C bond formation coupled to a second electron transfer, four proton-transfer and tautomerization steps, and four steps where Wat644 and Wat789 move about and mediate these events. The water diad is the minimal requisite element that endows StaP with function Streptomyces longisporoflavus dichloroarcyriaflavin A + 2 CO2 + 6 H2O + 4 NAD+
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Synonyms

EC Number Synonyms Comment Organism
1.13.12.17 cytochrome P450 StaP
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 Streptomyces longisporoflavus