Strictosidine

Strictosidine

Names
IUPAC name Methyl (2S,3R,4S)-3-ethenyl-4-([(1S)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl]methyl)-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylate
Other names Isovincoside
Identifiers
CAS Number	20824-29-7
3D model (Jmol)	Interactive image
ChemSpider	141721
PubChem CID	161336
InChI InChI=1S/C27H34N2O9/c1-3-13-16(10-19-21-15(8-9-28-19)14-6-4-5-7-18(14)29-21)17(25(34)35-2)12-36-26(13)38-27-24(33)23(32)22(31)20(11-30)37-27/h3-7,12-13,16,19-20,22-24,26-33H,1,8-11H2,2H3/t13-,16+,19+,20-,22-,23+,24-,26+,27+/m1/s1 Key: XBAMJZTXGWPTRM-NTXHKPOFSA-N
SMILES COC(=O)C1=CO[C@H]([C@@H]([C@@H]1C[C@H]2C3=C(CCN2)C4=CC=CC=C4N3)C=C)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O
Properties
Chemical formula	C27H34N2O9
Molar mass	530.57 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

Strictosidine is a terpene indole alkaloid formed by the condensation of tryptamine with secologanin by the enzyme strictosidine synthase. Strictosidine is the base molecule for numerous pharmaceutically valuable metabolites including quinine, camptothecin, ajmalicine, serpentine, vinblastine and vincristine.

Strictosidine is found in the following plant families.

Recent efforts in metabolic engineering have permitted the synthesis of strictosidine by yeast (Saccharomyces cerevisiae). This was accomplished by adding 21 genes and 3 gene deletions.