Desacetoxyvindoline
Names
IUPAC name
Methyl 3-hydroxy-16-methoxy-1-methyl-6,7-didehydro-2β,5α,12β,19α-aspidospermidine-3β-carboxylate
Systematic IUPAC name
Methyl (3aR,3a1S,5R,5aR,10bR)-3a-ethyl-5-hydroxy-8-methoxy-6-methyl-3a,3a1,4,5,5a,6,11,12-octahydro-1H-indolizino[8,1-cd]carbazole-5-carboxylate
Other names
Deacetoxyvindoline
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
  • InChI=1S/C23H30N2O4/c1-5-21-9-6-11-25-12-10-22(18(21)25)16-8-7-15(28-3)13-17(16)24(2)19(22)23(27,14-21)20(26)29-4/h6-9,13,18-19,27H,5,10-12,14H2,1-4H3/t18-,19+,21-,22+,23+/m0/s1
    Key: WNKDGPXNFMMOEJ-RNJSZURPSA-N
  • InChI=1/C23H30N2O4/c1-5-21-9-6-11-25-12-10-22(18(21)25)16-8-7-15(28-3)13-17(16)24(2)19(22)23(27,14-21)20(26)29-4/h6-9,13,18-19,27H,5,10-12,14H2,1-4H3/t18-,19+,21-,22+,23+/m0/s1
    Key: WNKDGPXNFMMOEJ-RNJSZURPBV
  • CC[C@]12C[C@@]([C@H]3[C@@]4([C@H]1N(CC4)CC=C2)c5ccc(cc5N3C)OC)(C(=O)OC)O
Properties
C23H30N2O4
Molar mass 398.503 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Desacetoxyvindoline is a terpene indole alkaloid produced by the plant Catharanthus roseus. Desacetoxyvindoline is a product formed by the methylation of the nitrogen on the indole ring by the enzyme 3-hydroxy-16-methoxy-2,3-dihydrotabersonine N-methyltransferase (NMT).[1] The metabolite is a substrate for desacetoxyvindoline 4-hydroxylase (D4H) which catalyzes a hydroxylation to yield deacetylvindoline.[2]

References

  1. ↑ Liscombe, DK; Usera, AR; O'Connor, SE (2 November 2010). "Homolog of tocopherol C methyltransferases catalyzes N methylation in anticancer alkaloid biosynthesis". Proceedings of the National Academy of Sciences of the United States of America. 107 (44): 18793–8. Bibcode:2010PNAS..10718793L. doi:10.1073/pnas.1009003107. PMC 2973921. PMID 20956330.
  2. ↑ Vazquez-Flota, Felipe; De Carolis, Emidio; Alarco, Anne-Marie; De Luca, Vincenzo (1997). "Molecular cloning and characterization of desacetoxyvindoline-4-hydroxylase, a 2-oxoglutarate dependent-dioxygenase involved in the biosynthesis of vindoline in Catharanthus roseus (L.) G. Don". Plant Molecular Biology. 34 (6): 935–948. doi:10.1023/A:1005894001516. PMID 9290645. S2CID 33942703.
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