M1W080 · TCPC_CLAP2
- ProteinCytochrome P450 monooxygenase tcpC
- GenetcpC
- StatusUniProtKB reviewed (Swiss-Prot)
- Amino acids505 (go to sequence)
- Protein existenceEvidence at transcript level
- Annotation score3/5
Function
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).
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).
Cofactor
Pathway
Secondary metabolite biosynthesis.
Features
Showing features for binding site.
GO annotations
Aspect | Term | |
---|---|---|
Molecular Function | heme binding | |
Molecular Function | iron ion binding | |
Molecular Function | monooxygenase activity | |
Molecular Function | oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen |
Keywords
- Molecular function
- Ligand
Enzyme and pathway databases
Names & Taxonomy
Protein names
- Recommended nameCytochrome P450 monooxygenase tcpC
- EC number
- Alternative names
Gene names
Organism names
- Strain
- Taxonomic lineageEukaryota > Fungi > Dikarya > Ascomycota > Pezizomycotina > Sordariomycetes > Hypocreomycetidae > Hypocreales > Clavicipitaceae > Claviceps
Accessions
- Primary accessionM1W080
Proteomes
Organism-specific databases
PTM/Processing
Features
Showing features for signal, chain, glycosylation.
Type | ID | Position(s) | Description | |||
---|---|---|---|---|---|---|
Signal | 1-26 | |||||
Sequence: MVFKMVMLKDVFPILVFLVALRLLKS | ||||||
Chain | PRO_0000437709 | 27-505 | Cytochrome P450 monooxygenase tcpC | |||
Sequence: QIAQWMIESIVTKLLQALNPVHDSLGKGISGPRWQYLNGQTLDKFLDGREKVQEWQKYGPVYRIWAGTTPEIVITKPEDVRAFHVDSSRHNKARSSNAGWLFHQLLGECMGLISGTRWIKVRSEFEPAFSHSAITMKAAEVSNDAQCYVNKLEKSRSSSFTVQAAEAVARFPFFCTATHLYGELSEEERNELWELGQRNLKMMGHVLSGGLFRFPIARWLYRSAVQDLESFLCDWASFNERIYKKKVGCGAKTPIVSAWKKVIDGDLTREEAIHTLSEILFANLDVATGNLSWLVIYLAANEDIQRQVVEEISQHRHELDHYCARKDTLLAYCVLETLRLRPFTAFSIPESSPNQKVLHGFTVPGNTSVVVNTLAINYNAAFWGDKAEVFSPNRFHSINRLALRYNLFTFGMGTRKCLGSHFAEMMMKYFAMHLLNRFSLHIPVEKDRSKAQTEDTSMSTWVPISDKEVALQKRTMGLF | ||||||
Glycosylation | 316 | N-linked (GlcNAc...) asparagine | ||||
Sequence: N | ||||||
Glycosylation | 392 | N-linked (GlcNAc...) asparagine | ||||
Sequence: N |
Keywords
- PTM
PTM databases
Expression
Induction
Expression is positively regulated by the thioclapurine cluster-specific transcription factor tcpZ (PubMed:27390873).
Interaction
Protein-protein interaction databases
Structure
Sequence
- Sequence statusComplete
- Sequence processingThe displayed sequence is further processed into a mature form.
- Length505
- Mass (Da)57,680
- Last updated2013-05-01 v1
- Checksum40988639DD66D4CA
Keywords
- Technical term