Reaction participants Show >> << Hide
- Name help_outline 3,17-didehydrostemmadenine Identifier CHEBI:142668 Charge 1 Formula C21H23N2O3 InChIKeyhelp_outline QWXYZCJEXYQNEI-OSZHWHEXSA-N SMILEShelp_outline C12=C(C=CC=C1)NC=3[C@]([C@@]4(/C(/C[N+](=CC4)CCC32)=C\C)[H])(C(=O)OC)C=O 2D coordinates Mol file for the small molecule Search links Involved in 5 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline 17-dehydropreakuammicine Identifier CHEBI:230469 Charge 1 Formula C21H23N2O3 InChIKeyhelp_outline OBUYIUIFFBCOOV-OQTQPSEISA-O SMILEShelp_outline C12=C(C=CC=C1)N=C3[C@]([C@@]4(/C(/C[NH+]5[C@@H](C4)[C@]32CC5)=C\C)[H])(C(=O)OC)C=O 2D coordinates Mol file for the small molecule Search links Involved in 3 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:79587 | RHEA:79588 | RHEA:79589 | RHEA:79590 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
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Publications
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Solution of the multistep pathway for assembly of corynanthean, strychnos, iboga, and aspidosperma monoterpenoid indole alkaloids from 19E-geissoschizine.
Qu Y., Easson M.E.A.M., Simionescu R., Hajicek J., Thamm A.M.K., Salim V., De Luca V.
Monoterpenoid indole alkaloids (MIAs) possess a diversity of alkaloid skeletons whose biosynthesis is poorly understood. A bioinformatic search of candidate genes, combined with their virus-induced gene silencing, targeted MIA profiling and in vitro/in vivo pathway reconstitution identified and fu ... >> More
Monoterpenoid indole alkaloids (MIAs) possess a diversity of alkaloid skeletons whose biosynthesis is poorly understood. A bioinformatic search of candidate genes, combined with their virus-induced gene silencing, targeted MIA profiling and in vitro/in vivo pathway reconstitution identified and functionally characterized six genes as well as a seventh enzyme reaction required for the conversion of 19<i>E</i>-geissoschizine to tabersonine and catharanthine. The involvement of pathway intermediates in the formation of four MIA skeletons is described, and the role of stemmadenine-<i>O</i>-acetylation in providing necessary reactive substrates for the formation of iboga and aspidosperma MIAs is described. The results enable the assembly of complex dimeric MIAs used in cancer chemotherapy and open the way to production of many other biologically active MIAs that are not easily available from nature. << Less
Proc. Natl. Acad. Sci. U.S.A. 115:3180-3185(2018) [PubMed] [EuropePMC]
This publication is cited by 15 other entries.
Comments
RHEA:79587 part of RHEA:58520 This reaction can occur spontaneously.