Cytochrome P450 monooxygenase; part of the gene cluster that mediates the biosynthesis of the fungal neurotoxin cyclopiazonic acid (CPA), a nanomolar inhibitor of Ca(2+)-ATPase with a unique pentacyclic indole tetramic acid scaffold (PubMed:21608094). The hybrid two module polyketide synthase-nonribosomal peptide synthetase (PKS-NRPS) cpaS incorporates acetyl-CoA, malonyl-CoA, and tryptophan (Trp) and utilizes a C-terminal redox-incompetent reductase domain to make and release the tryptophan tetramic acid, cyclo-acetoacetyl-L-tryptophan (c-AATrp), as the first intermediate in the pathway. CpaS catalyzes a Dieckmann-type cyclization on the N-acetoacetyl-Trp intermediate bound in thioester linkage to the phosphopantetheinyl arm of the T domain to form and release c-AATrp (PubMed:21608094, PubMed:19663400). CpaD than regiospecifically dimethylallylates c-AATrp to form beta-cyclopiazonic acid. CpaD discriminates against free Trp but accepts tryptophan-containing thiohydantoins, diketopiperazines, and linear peptides as substrates for C4-prenylation and also acts as regiospecific O-dimethylallyltransferase (DMAT) on a tyrosine-derived tetramic acid (PubMed:21608094, PubMed:19877600). The beta-cyclopiazonate dehydrogenase cpaO then carries out the dehydrogenation of beta-CPA to yield an unstable enimine product, which is captured by intramolecular cyclization to create the pentacyclic fused scaffold of alpha-cyclopiazonate (PubMed:21608094). Fimally, the cytochrome P450 monooxygenase cpaH mediates the conversion of CPA into the less toxic 2-oxocyclopiazonic acid, the end product of the CPA pathway in A.oryza (PubMed:21608094).

Belongs to the cytochrome P450 family.

509 amino acids

MSQFAREIVRNAIYNTSSPDADSVSLRKATTTILLIGVTYCILVGIYRVTLHPLAKYPGPKLAAVTRLWHSYHLCTGDIVSVLSRAHEAYGPVLRIAPDEVLFISSRAWDDIYGARPGKPEMDKDTPLYKGPTAPHSIVTVDGELHRFYRRLLAKGFSDAALREQEPVIQRNINLLVEKLHKEVAAGKTPEMTAWFNYATFDLIGELAFGETYGCLENSHYHPWVEMILEVMKLRAMTHAVGYYPWIFHILMWFVPKSLREKFVTHRRYTHDKVQRRMDQKIHYKDLTTNLVDPQNGLERYEIDGNCSTLIIAGSETTATALSATLYFLTQNENAKRKVIGEIRTTFNNAGDINSISVNQLKYLSACMNEALRIFPPGPAVFPRRVPQGGDFIDGHWIPGGTQVGIAHYCINRSRRNFVDPDKFIPERWLGDPTYQTDDRHAVQPFSYGPRNCIAHNLARLEMRLVLARLIWEFDWELAPGSERWEEEALVFNVWSTKPLMIKFTPVAR

58.2 kDa

(Note: Representative image - actual molecular weight may vary depending on tag type and expression method)

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