Reaction participants Show >> << Hide
- Name help_outline 17-dehydropreakuammicine hydrate Identifier CHEBI:230472 Charge 1 Formula C21H25N2O4 InChIKeyhelp_outline TZLHPXHOPLCTTE-KSPARTEWSA-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)O 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 akuammicine Identifier CHEBI:142754 Charge 1 Formula C20H23N2O2 InChIKeyhelp_outline AGZMFTKKLPHOMT-DUJTVWLASA-O SMILEShelp_outline C=12[C@@]3([C@H]4[NH+](CC3)C\C(\[C@@](C1C(=O)OC)(C4)[H])=C\C)C5=CC=CC=C5N2 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 formate Identifier CHEBI:15740 (CAS: 71-47-6) help_outline Charge -1 Formula CHO2 InChIKeyhelp_outline BDAGIHXWWSANSR-UHFFFAOYSA-M SMILEShelp_outline [H]C([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 99 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 InChIKeyhelp_outline GPRLSGONYQIRFK-UHFFFAOYSA-N SMILEShelp_outline [H+] 2D coordinates Mol file for the small molecule Search links Involved in 10,232 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:79595 | RHEA:79596 | RHEA:79597 | RHEA:79598 | |
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| 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:79595 part of RHEA:58520 This reaction can occur spontaneously.