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tcpC

Gene
tcpC
Protein
Cytochrome P450 monooxygenase tcpC
Organism
Claviceps purpurea (strain 20.1)
Length
505 amino acids
Function
Cytochrome P450 monooxygenase; part of the gene cluster that mediates the biosynthesis of an unusual class of epipolythiodioxopiperazines (ETPs) lacking the reactive thiol group important for toxicity (PubMed:27390873). Firstly, L-tyrosine is prenylated by tcpD, before undergoing condensation with L-glycine in a reaction catalyzed by the NRPS tcpP leading to the diketopiperazine (DKP) backbone (PubMed:27390873). Afterwards the alpha-carbon of tyrosine is oxidized by the cytochrome P450 tcpC to form a hydroxyl group (PubMed:27390873). However, in contrast other ETP biosynthesis pathways studied so far, tcpC is not able to bishydroxylate the DKP at both alpha-carbon positions, but hydroxylates the alpha-carbon of the tyrosine part and the nitrogen of the glycine part (PubMed:27390873). The next steps involve an alpha,beta-elimination reaction catalyzed by tcpI, a methylation by the methyltransferase tcpN the action of the four enzyme cascade tcpG/K/J/I (PubMed:27390873). Due to a dysfunctional cytochrome P450 monooxygenase tcpC, the pathway leads to the biosynthesis of probable non-toxic metabolites lacking the reactive thiol group (PubMed:27390873).
Similarity
Belongs to the cytochrome P450 family.
Mass
57.68 kDa
Sequence
MVFKMVMLKDVFPILVFLVALRLLKSQIAQWMIESIVTKLLQALNPVHDSLGKGISGPRWQYLNGQTLDKFLDGREKVQEWQKYGPVYRIWAGTTPEIVITKPEDVRAFHVDSSRHNKARSSNAGWLFHQLLGECMGLISGTRWIKVRSEFEPAFSHSAITMKAAEVSNDAQCYVNKLEKSRSSSFTVQAAEAVARFPFFCTATHLYGELSEEERNELWELGQRNLKMMGHVLSGGLFRFPIARWLYRSAVQDLESFLCDWASFNERIYKKKVGCGAKTPIVSAWKKVIDGDLTREEAIHTLSEILFANLDVATGNLSWLVIYLAANEDIQRQVVEEISQHRHELDHYCARKDTLLAYCVLETLRLRPFTAFSIPESSPNQKVLHGFTVPGNTSVVVNTLAINYNAAFWGDKAEVFSPNRFHSINRLALRYNLFTFGMGTRKCLGSHFAEMMMKYFAMHLLNRFSLHIPVEKDRSKAQTEDTSMSTWVPISDKEVALQKRTMGLF

Gene
tcpC
Protein
Toxin coregulated pilus biosynthesis outer membrane protein C
Organism
Vibrio cholerae serotype O1 (strain ATCC 39315 / El Tor Inaba N16961)
Length
489 amino acids
Function
Involved in TCP pilus biogenesis.
Mass
53.89 kDa
Sequence
MKKTIISTLVIGLVSGCSNTNLLKDNLASEQSVINLSKSSNEAKSRNIEFLSGAYLSERKVPKHDIKFSGKYVEFESKSPIELIDVLDGLSKQYNIQYVFSDELEDENSEENKKSSGSSSAKKIKYSGPLAGFFDYLSSAYNMHFEFGHNNLVKAYHYKNQVFNLQQYFDDNKFSSSMQIGGTSGTSSGLKGTADTAIESNSWEKIDEFLSASLGETGKFTIFEDYSLVTVKARPDKFLLLHTFFDKLINESKMQIAVDYRVVSLSEERLNQLAAKFGIENAGKYSITSDMVDAISLSQVGGGLGASYRSASARLDAVVNELSQEVMHEGHFIGIPNRVMPLNVTTNSKYISSIETTKDTNTDEETRTVKVSDLVTGFSMMVMPKILDDGRIQISSGFSRKQLVSIGTAQGITLPTVDENESMNTVTMNPGEVRLAMLFKDNYIQNSNGVQLLGGGTENKKSARYIAVLVGASSYKTNDLASNRVNIYD