Deacetylvindoline

Deacetylvindoline is a terpene indole alkaloid produced by Catharanthus roseus. Deacetylvindoline is the product of a hydroxylation of desacetoxyvindoline by deacetoxyvindoline 4-hydroxylase (D4H).^[1] It is a substrate for deacetylvindoline O-acetyltransferase (DAT) which acetylates a hydroxy group to form vindoline, one of the two immediate precursors for the formation of the pharmacetucially valuable bisindole alkaloid vinblastine.^[2]

Deacetylvindoline

Names
IUPAC name Methyl 3β,4β-dihydroxy-16-methoxy-1-methyl-6,7-didehydro-2β,5α,12β,19α-aspidospermidine-3-carboxylate
Systematic IUPAC name Methyl (3aR,3a^1R,4R,5S,5aR,10bR)-3b-ethyl-4,5-dihydroxy-8-methoxy-6-methyl-3a,3a^1,4,5,5a,6,11,12-octahydro-1H-indolizino[8,1-cd]carbazole-5-carboxylate
Other names Desacetylvindoline; 17-O-Deacetylvindoline
Identifiers
CAS Number	3633-92-9
3D model (JSmol)	Interactive image
ChEBI	CHEBI:18362
ChemSpider	228679
PubChem CID	260534
UNII	24ETH7DXT4^Y
InChI InChI=1S/C23H30N2O5/c1-5-21-9-6-11-25-12-10-22(17(21)25)15-8-7-14(29-3)13-16(15)24(2)18(22)23(28,19(21)26)20(27)30-4/h6-9,13,17-19,26,28H,5,10-12H2,1-4H3/t17-,18+,19+,21+,22+,23-/m0/s1 Key: ZDKMPOJNYNVYLA-PEGGBQQISA-N InChI=1/C23H30N2O5/c1-5-21-9-6-11-25-12-10-22(17(21)25)15-8-7-14(29-3)13-16(15)24(2)18(22)23(28,19(21)26)20(27)30-4/h6-9,13,17-19,26,28H,5,10-12H2,1-4H3/t17-,18+,19+,21+,22+,23-/m0/s1 Key: ZDKMPOJNYNVYLA-PEGGBQQIBO
SMILES CC[C@@]12C=CCN3[C@@H]1[C@@]4(CC3)c5ccc(cc5N([C@H]4[C@]([C@@H]2O)(C(=O)OC)O)C)OC
Properties
Chemical formula	C23H30N2O5
Molar mass	414.502 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

References

1. Vazquez-Flota, De Carolis, Alarco and De Luca (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
2. Power, Kurz and De Luca (1990) Purification and characterization of acetylcoenzyme A: Deacetylvindoline 4-O-acetyltransferase from Catharanthus roseus. Archives of Biochemistry and Biophysics. 279(2). 370-376