Preakuammicine

Preakuammicine
Names
IUPAC name
Methyl (16α,19E)-16-(hydroxymethyl)-1,2-didehydrocur-19-en-17-oate
Other names
methyl (11S,12E,17S)-12-ethylidene-10-(hydroxymethyl)-8,14-diazapentacyclo[9.5.2.01,9.02,7.014,17]octadeca-2,4,6,8-tetraene-10-carboxylate
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C21H24N2O3/c1-3-13-11-23-9-8-20-14-6-4-5-7-16(14)22-18(20)21(12-24,19(25)26-2)15(13)10-17(20)23/h3-7,15,17,24H,8-12H2,1-2H3/b13-3-/t15-,17-,20+,21-/m0/s1
    Key: DSOCELULQRKOMA-OQTQPSEISA-N
  • InChI=1/C21H24N2O3/c1-3-13-11-23-9-8-20-14-6-4-5-7-16(14)22-18(20)21(12-24,19(25)26-2)15(13)10-17(20)23/h3-7,15,17,24H,8-12H2,1-2H3/b13-3-/t15-,17-,20+,21-/m0/s1
    Key: DSOCELULQRKOMA-OQTQPSEIBY
  • C/C=C\1/CN2CC[C@@]34[C@@H]2C[C@@H]1[C@](C3=Nc5c4cccc5)(CO)C(=O)OC
Properties
C21H24N2O3
Molar mass 352.434 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Preakuammicine is a terpene indole alkaloid.[2] Preakuammicine is thought to be formed from 4,21-dehydrogeissoschizine and lead to synthesis of stemmadenine. The enzymes involved in preakuammicine formation and those which use it as a substrate are currently unknown.

References

  1. ^ "Preakuammicine | Chemical Substance Information". J-GLOBAL.
  2. ^ Benayad, Sarah; Ahamada, Kadiria; Lewin, Guy; Evanno, Laurent; Poupon, Erwan (March 2016). "Preakuammicine: A Long-Awaited Missing Link in the Biosynthesis of Monoterpene Indole Alkaloids". European Journal of Organic Chemistry. 2016 (8): 1494–1499. doi:10.1002/ejoc.201600102.


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