Rhea - reaction knowledgebase

Enzymes

UniProtKB ^help_outline	1 proteins
Enzyme class ^help_outline	EC 1.14.19.51 (S)-corytuberine synthase
GO Molecular Function ^help_outline	GO:0102963 (S)-corytuberine synthase activity

Reaction participants Show >> << Hide

Name ^help_outline (S)-reticuline Identifier CHEBI:57873 Charge 1 Formula C19H24NO4 InChIKey^help_outline BHLYRWXGMIUIHG-HNNXBMFYSA-O SMILES^help_outline COc1ccc(C[C@@H]2[NH+](C)CCc3cc(OC)c(O)cc23)cc1O 2D coordinates Mol file for the small molecule Search links Involved in 8 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Name ^help_outline O₂ Identifier CHEBI:15379 (CAS: 7782-44-7) ^help_outline Charge 0 Formula O2 InChIKey^help_outline MYMOFIZGZYHOMD-UHFFFAOYSA-N SMILES^help_outline O=O 2D coordinates Mol file for the small molecule Search links Involved in 2,648 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Name^help_outline reduced [NADPH—hemoprotein reductase] Identifier RHEA-COMP:11964 Reactive part ^help_outline
- Name ^help_outline FMNH₂ Identifier CHEBI:57618 (Beilstein: 6258176) ^help_outline Charge -2 Formula C17H21N4O9P InChIKey^help_outline YTNIXZGTHTVJBW-SCRDCRAPSA-L SMILES^help_outline Cc1cc2Nc3c([nH]c(=O)[nH]c3=O)N(C[C@H](O)[C@H](O)[C@H](O)COP([O-])([O-])=O)c2cc1C 2D coordinates Mol file for the small molecule Search links Involved in 771 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Search links Involved in 711 reaction(s) Find proteins in UniProtKB for this molecule
Name ^help_outline (S)-corytuberine Identifier CHEBI:81200 (CAS: 517-56-6) ^help_outline Charge 0 Formula C19H21NO4 InChIKey^help_outline WHFUDAOCYRYAKQ-LBPRGKRZSA-N SMILES^help_outline C1=2C=3[C@@](N(CC1)C)(CC4=C(C3C(=C(C2)OC)O)C(=C(C=C4)OC)O)[H] 2D coordinates Mol file for the small molecule Search links Involved in 2 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Name ^help_outline H⁺ Identifier CHEBI:15378 Charge 1 Formula H InChIKey^help_outline GPRLSGONYQIRFK-UHFFFAOYSA-N SMILES^help_outline [H+] 2D coordinates Mol file for the small molecule Search links Involved in 9,176 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Name ^help_outline H₂O Identifier CHEBI:15377 (Beilstein: 3587155; CAS: 7732-18-5) ^help_outline Charge 0 Formula H2O InChIKey^help_outline XLYOFNOQVPJJNP-UHFFFAOYSA-N SMILES^help_outline [H]O[H] 2D coordinates Mol file for the small molecule Search links Involved in 6,048 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Name^help_outline oxidized [NADPH—hemoprotein reductase] Identifier RHEA-COMP:11965 Reactive part ^help_outline
- Name ^help_outline FMN Identifier CHEBI:58210 Charge -3 Formula C17H18N4O9P InChIKey^help_outline ANKZYBDXHMZBDK-SCRDCRAPSA-K SMILES^help_outline C12=NC([N-]C(C1=NC=3C(N2C[C@@H]([C@@H]([C@@H](COP(=O)([O-])[O-])O)O)O)=CC(=C(C3)C)C)=O)=O 2D coordinates Mol file for the small molecule Search links Involved in 781 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Search links Involved in 711 reaction(s) Find proteins in UniProtKB for this molecule

Cross-references

	RHEA:51540	RHEA:51541	RHEA:51542	RHEA:51543
Reaction direction	undefined	left-to-right	right-to-left	bidirectional
UniProtKB ^help_outline	1 proteins
EC numbers ^help_outline	1.14.19.51
Gene Ontology ^help_outline	GO:0102963
MetaCyc ^help_outline		RXN-9314

Publications

Molecular cloning and characterization of CYP80G2, a cytochrome P450 that catalyzes an intramolecular C-C phenol coupling of (S)-reticuline in magnoflorine biosynthesis, from cultured Coptis japonica cells.

Ikezawa N., Iwasa K., Sato F.

Cytochrome P450s (P450) play a key role in oxidative reactions in plant secondary metabolism. Some of them, which catalyze unique reactions other than the standard hydroxylation, increase the structural diversity of plant secondary metabolites. In isoquinoline alkaloid biosyntheses, several unique ... >> More

Cytochrome P450s (P450) play a key role in oxidative reactions in plant secondary metabolism. Some of them, which catalyze unique reactions other than the standard hydroxylation, increase the structural diversity of plant secondary metabolites. In isoquinoline alkaloid biosyntheses, several unique P450 reactions have been reported, such as methylenedioxy bridge formation, intramolecular C-C phenol-coupling and intermolecular C-O phenol-coupling reactions. We report here the isolation and characterization of a C-C phenol-coupling P450 cDNA (CYP80G2) from an expressed sequence tag library of cultured Coptis japonica cells. Structural analysis showed that CYP80G2 had high amino acid sequence similarity to Berberis stolonifera CYP80A1, an intermolecular C-O phenol-coupling P450 involved in berbamunine biosynthesis. Heterologous expression in yeast indicated that CYP80G2 had intramolecular C-C phenol-coupling activity to produce (S)-corytuberine (aporphine-type) from (S)-reticuline (benzylisoquinoline type). Despite this intriguing reaction, recombinant CYP80G2 showed typical P450 properties: its C-C phenol-coupling reaction required NADPH and oxygen and was inhibited by a typical P450 inhibitor. Based on a detailed substrate-specificity analysis, this unique reaction mechanism and substrate recognition were discussed. CYP80G2 may be involved in magnoflorine biosynthesis in C. japonica, based on the fact that recombinant C. japonica S-adenosyl-L-methionine:coclaurine N-methyltransferase could convert (S)-corytuberine to magnoflorine. << Less

J. Biol. Chem. 283:8810-8821(2008) [PubMed] [EuropePMC]

RHEA:51540 (S)-reticuline + O2 + reduced [NADPH--hemoprotein reductase] = (S)-corytuberine + 2 H(+) + 2 H2O + oxidized [NADPH--hemoprotein reductase]

Enzymes

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Cross-references

Publications

Molecular cloning and characterization of CYP80G2, a cytochrome P450 that catalyzes an intramolecular C-C phenol coupling of (S)-reticuline in magnoflorine biosynthesis, from cultured Coptis japonica cells.