deacetylvindoline

{{Chembox

| ImageFile = Deacetylvindoline.svg

| ImageSize = 200px

| IUPACName = Methyl 3β,4β-dihydroxy-16-methoxy-1-methyl-6,7-didehydro-2β,5α,12β,19α-aspidospermidine-3-carboxylate

| SystematicName = Methyl (3aR,3a1R,4R,5S,5aR,10bR)-3b-ethyl-4,5-dihydroxy-8-methoxy-6-methyl-3a,3a1,4,5,5a,6,11,12-octahydro-1H-indolizino[8,1-cd]carbazole-5-carboxylate

| OtherNames = Desacetylvindoline; 17-O-Deacetylvindoline

|Section1={{Chembox Identifiers

| CASNo = 3633-92-9

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 24ETH7DXT4

| PubChem = 260534

| ChemSpiderID = 228679

| ChEBI = 18362

| 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

| 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

| InChIKey = ZDKMPOJNYNVYLA-PEGGBQQIBO

| StdInChI = 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

| StdInChIKey = ZDKMPOJNYNVYLA-PEGGBQQISA-N

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|Section2={{Chembox Properties

| C=23 | H=30 | N=2 | O=5

| Appearance =

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|Section3={{Chembox Hazards

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Deacetylvindoline is a terpene indole alkaloid produced by Catharanthus roseus. Deacetylvindoline is the product of a hydroxylation of desacetoxyvindoline by deacetoxyvindoline 4-hydroxylase (D4H).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 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.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

References