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Literature summary for 1.14.14.1 extracted from

  • Branco, R.J.; Seifert, A.; Budde, M.; Urlacher, V.B.; Ramos, M.J.; Pleiss, J.
    Anchoring effects in a wide binding pocket: The molecular basis of regioselectivity in engineered cytochrome P450 monooxygenase from B. megaterium (2008), Proteins, 73, 597-607.
    View publication on PubMed

Cloned(Commentary)

Cloned (Comment) Organism
expression in Escherichia coli BL21 (DE3) using the pET281 expression system Priestia megaterium

Crystallization (Commentary)

Crystallization (Comment) Organism
molecular dynamics simulations on two CYP102A1 mutants in complex with (-)-alpha-pinene to explore the molecular mechanism of substrate recognition and to predict regioselectivity. Priestia megaterium

Protein Variants

Protein Variants Comment Organism
A74G/F87G/L188Q site-directed mutagenesis. The introduction of a smaller amino acid at position 87 results in a more active monooxygenase and a different product profile for the oxidation of substrate (-)-alpha-pinene. Priestia megaterium
A74G/F87V/L188Q site-directed mutagenesis. The introduction of a smaller amino acid at position 87 results in a more active monooxygenase and a different product profile for the oxidation of substrate (-)-alpha-pinene. Priestia megaterium
A74G/L188Q site-directed mutagenesis. MD simulations of the double mutant A74G L188Q (GQ) show that the substrate is blocked from accessing the heme oxygen by the side chain of the F87, when it adopts the conformation found in the X-ray structure. Priestia megaterium

Organism

Organism UniProt Comment Textmining
Priestia megaterium P14779 expression in Escherichia coli BL21 (DE3) using the pET281 expression system
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Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(-)-alpha-pinene + [reduced NADPH-hemoprotein reductase] + O2 mutant A74G/F87G/L188Q Priestia megaterium myrtenol + [oxidized NADPH-hemoprotein reductase] + H2O mutant A74G/F87G/L188Q, 13% pinene oxide, 77% verbenol, 10% myrtenol ?
(-)-alpha-pinene + [reduced NADPH-hemoprotein reductase] + O2 mutant A74G/F87V/L188Q Priestia megaterium myrtenol + [oxidized NADPH-hemoprotein reductase] + H2O mutant A74G/F87V/L188Q, 70% pinene oxide, 20% verbenol, 10% myrtenol ?
(-)-alpha-pinene + [reduced NADPH-hemoprotein reductase] + O2 mutant A74G/F87G/L188Q Priestia megaterium pinene oxide + [oxidized NADPH-hemoprotein reductase] + H2O mutant A74G/F87V/L188Q, 13% pinene oxide, 77% verbenol, 10% myrtenol ?
(-)-alpha-pinene + [reduced NADPH-hemoprotein reductase] + O2 mutant A74G/F87V/L188Q Priestia megaterium pinene oxide + [oxidized NADPH-hemoprotein reductase] + H2O mutant A74G/F87V/L188Q, 70% pinene oxide, 20% verbenol, 10% myrtenol ?
(-)-alpha-pinene + [reduced NADPH-hemoprotein reductase] + O2 mutant A74G/L188Q Priestia megaterium pinene oxide + [oxidized NADPH-hemoprotein reductase] + H2O mutant A74G/L188Q, 85% pinene oxide, 15% verbenol ?
(-)-alpha-pinene + [reduced NADPH-hemoprotein reductase] + O2 mutant A74G/F87G/L188Q Priestia megaterium verbenol + [oxidized NADPH-hemoprotein reductase] + H2O mutant A74G/F87G/L188Q, 13% pinene oxide, 77% verbenol, 10% myrtenol ?
(-)-alpha-pinene + [reduced NADPH-hemoprotein reductase] + O2 mutant A74G/F87V/L188Q Priestia megaterium verbenol + [oxidized NADPH-hemoprotein reductase] + H2O mutant A74G/F87V/L188Q, 70% pinene oxide, 20% verbenol, 10% myrtenol ?
(-)-alpha-pinene + [reduced NADPH-hemoprotein reductase] + O2 mutant A74G/L188Q Priestia megaterium verbenol + [oxidized NADPH-hemoprotein reductase] + H2O mutant A74G/L188Q, 85% pinene oxide, 15% verbenol ?
(-)-beta-pinene + [reduced NADPH-hemoprotein reductase] + O2 mutant A74G/F87G/L188Q Priestia megaterium myrtanal + [oxidized NADPH-hemoprotein reductase] + H2O mutant A74G/F87G/L188Q, 40% pino-carveol, 60% myrtanal ?
(-)-beta-pinene + [reduced NADPH-hemoprotein reductase] + O2 mutant A74G/F87V/L188Q Priestia megaterium myrtanal + [oxidized NADPH-hemoprotein reductase] + H2O mutant A74G/F87V/L188Q, 68% pino-carveol, 32% myrtanal ?
(-)-beta-pinene + [reduced NADPH-hemoprotein reductase] + O2 mutant A74G/F87G/L188Q Priestia megaterium pino-carveol + [oxidized NADPH-hemoprotein reductase] + H2O mutant A74G/F87G/L188Q, 40% pino-carveol, 60% myrtanal ?
(-)-beta-pinene + [reduced NADPH-hemoprotein reductase] + O2 mutant A74G/F87V/L188Q Priestia megaterium pino-carveol + [oxidized NADPH-hemoprotein reductase] + H2O mutant A74G/F87V/L188Q, 68% pino-carveol, 32% myrtanal ?
additional information wild type CYP102A1 has no oxidizing activity toward (–)-alpha- and (–)-beta-pinene Priestia megaterium ?
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Synonyms

Synonyms Comment Organism
CYP102A1
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Priestia megaterium
P450 BM3
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Priestia megaterium