Reaction participants Show >> << Hide
- Name help_outline dihydroalstonine Identifier CHEBI:142534 Charge 1 Formula C21H23N2O3 InChIKeyhelp_outline PFIUINHQUIEFCH-DLLGKBFGSA-N SMILEShelp_outline C=1C=CC2=C(C1)C=3CC=[N+]4[C@](C3N2)(C[C@]5([C@]([C@@H](OC=C5C(OC)=O)C)(C4)[H])[H])[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 A Identifier CHEBI:13193 Charge Formula R SMILEShelp_outline * 2D coordinates Mol file for the small molecule Search links Involved in 3,077 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline alstonine Identifier CHEBI:142530 (CAS: 47485-83-6) help_outline Charge 1 Formula C21H21N2O3 InChIKeyhelp_outline WYTGDNHDOZPMIW-RCBQFDQVSA-O SMILEShelp_outline C=1C=CC2=C(C1)C=3C=C[N+]4=C(C3N2)C[C@]5([C@]([C@@H](OC=C5C(OC)=O)C)(C4)[H])[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 AH2 Identifier CHEBI:17499 Charge 0 Formula RH2 SMILEShelp_outline *([H])[H] 2D coordinates Mol file for the small molecule Search links Involved in 3,005 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:58208 | RHEA:58209 | RHEA:58210 | RHEA:58211 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
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Publications
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Sarpagan bridge enzyme has substrate-controlled cyclization and aromatization modes.
Dang T.T., Franke J., Carqueijeiro I.S.T., Langley C., Courdavault V., O'Connor S.E.
Cyclization reactions that create complex polycyclic scaffolds are hallmarks of alkaloid biosynthetic pathways. We present the discovery of three homologous cytochrome P450s from three monoterpene indole alkaloid-producing plants (Rauwolfia serpentina, Gelsemium sempervirens and Catharanthus roseu ... >> More
Cyclization reactions that create complex polycyclic scaffolds are hallmarks of alkaloid biosynthetic pathways. We present the discovery of three homologous cytochrome P450s from three monoterpene indole alkaloid-producing plants (Rauwolfia serpentina, Gelsemium sempervirens and Catharanthus roseus) that provide entry into two distinct alkaloid classes, the sarpagans and the β-carbolines. Our results highlight how a common enzymatic mechanism, guided by related but structurally distinct substrates, leads to either cyclization or aromatization. << Less
Nat. Chem. Biol. 14:760-763(2018) [PubMed] [EuropePMC]
This publication is cited by 6 other entries.
Comments
This reaction can occur spontanously. RHEA:58208 part of RHEA:58128