Reaction participants Show >> << Hide
- Name help_outline dihydroprecondylocarpine acetate Identifier CHEBI:142770 Charge 1 Formula C23H29N2O4 InChIKeyhelp_outline QXQMGTOURBIIKD-RUMUXARQSA-N SMILEShelp_outline C12=C(C=CC=C1)NC=3[C@]([C@@]4(C(C=[N+](CC4)CCC32)CC)[H])(C(=O)OC)COC(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 catharanthine Identifier CHEBI:142675 Charge 1 Formula C21H25N2O2 InChIKeyhelp_outline CMKFQVZJOWHHDV-NQZBTDCJSA-O SMILEShelp_outline C1[C@@]2(C=C([C@@]3([C@@]1(C(OC)=O)C4=C(C5=C(C=CC=C5)N4)CC[NH+]3C2)[H])CC)[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 acetate Identifier CHEBI:30089 (CAS: 71-50-1) help_outline Charge -1 Formula C2H3O2 InChIKeyhelp_outline QTBSBXVTEAMEQO-UHFFFAOYSA-M SMILEShelp_outline CC([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 186 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:58580 | RHEA:58581 | RHEA:58582 | RHEA:58583 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
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Publications
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Missing enzymes in the biosynthesis of the anticancer drug vinblastine in Madagascar periwinkle.
Caputi L., Franke J., Farrow S.C., Chung K., Payne R.M.E., Nguyen T.-D., Dang T.-T.T., Soares Teto Carqueijeiro I., Koudounas K., Duge de Bernonville T., Ameyaw B., Jones D.M., Vieira I.J.C., Courdavault V., O'Connor S.E.
Vinblastine, a potent anticancer drug, is produced by <i>Catharanthus roseus</i> (Madagascar periwinkle) in small quantities, and heterologous reconstitution of vinblastine biosynthesis could provide an additional source of this drug. However, the chemistry underlying vinblastine synthesis makes i ... >> More
Vinblastine, a potent anticancer drug, is produced by <i>Catharanthus roseus</i> (Madagascar periwinkle) in small quantities, and heterologous reconstitution of vinblastine biosynthesis could provide an additional source of this drug. However, the chemistry underlying vinblastine synthesis makes identification of the biosynthetic genes challenging. Here we identify the two missing enzymes necessary for vinblastine biosynthesis in this plant: an oxidase and a reductase that isomerize stemmadenine acetate into dihydroprecondylocarpine acetate, which is then deacetoxylated and cyclized to either catharanthine or tabersonine via two hydrolases characterized herein. The pathways show how plants create chemical diversity and also enable development of heterologous platforms for generation of stemmadenine-derived bioactive compounds. << Less
Science 360:1235-1239(2018) [PubMed] [EuropePMC]
This publication is cited by 7 other entries.
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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.