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 (JSmol)	Interactive image;
ChemSpider	141721;
PubChem CID	161336;
CompTox Dashboard (EPA)	DTXSID40943068 ;
	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	530.574 g·mol−1
Melting point	193-197 °C
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

Strictosidine is formed by the Pictet–Spengler reaction condensation of tryptamine with secologanin by the enzyme strictosidine synthase. Thousands of strictosidine derivatives are sometimes referred to by the broad phrase of monoterpene indole alkaloids.[1][2] Strictosidine is the base molecule for numerous pharmaceutically valuable metabolites including quinine, camptothecin, ajmalicine, serpentine, vinblastine and vincristine.

Biosynthetic pathways help to define the subgroups of strictosidine derivatives. [3] [4]

Distribution

Strictosidine is found in the following plant families.

Recent efforts in metabolic engineering have permitted the synthesis of strictosidine by yeast (Saccharomyces cerevisiae).[5] This was accomplished by adding 21 genes and 3 gene deletions.

References

Mizukami, H; Nordlöv, H; Lee, S. L.; Scott, A. I. (1979). "Purification and properties of strictosidine synthetase (an enzyme condensing tryptamine and secologanin) from Catharanthus roseus cultured cells". Biochemistry. 18 (17): 3760–3. doi:10.1021/bi00584a018. PMID 476085.
Treimer, J. F.; Zenk, M. H. (1979). "Purification and properties of strictosidine synthase, the key enzyme in indole alkaloid formation". European Journal of Biochemistry / FEBS. 101 (1): 225–33. doi:10.1111/j.1432-1033.1979.tb04235.x. PMID 510306.
Plant Secondary Metabolism, David S Seigler, Springer 1998
Biochemistry of Plant Secondary Metabolism, Michael Wink, Blackwell 2010
Brown, S; Clastre, M; Courdavault, V; O'Connor, S. E. (2015). "De novo production of the plant-derived alkaloid strictosidine in yeast". Proceedings of the National Academy of Sciences. 112: 201423555. doi:10.1073/pnas.1423555112. PMC 4371906. PMID 25675512.

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.

[1] Mizukami, H; Nordlöv, H; Lee, S. L.; Scott, A. I. (1979). "Purification and properties of strictosidine synthetase (an enzyme condensing tryptamine and secologanin) from Catharanthus roseus cultured cells". Biochemistry. 18 (17): 3760–3. doi:10.1021/bi00584a018. PMID 476085.

[2] Treimer, J. F.; Zenk, M. H. (1979). "Purification and properties of strictosidine synthase, the key enzyme in indole alkaloid formation". European Journal of Biochemistry / FEBS. 101 (1): 225–33. doi:10.1111/j.1432-1033.1979.tb04235.x. PMID 510306.

[3] Plant Secondary Metabolism, David S Seigler, Springer 1998

[4] Biochemistry of Plant Secondary Metabolism, Michael Wink, Blackwell 2010

[5] Brown, S; Clastre, M; Courdavault, V; O'Connor, S. E. (2015). "De novo production of the plant-derived alkaloid strictosidine in yeast". Proceedings of the National Academy of Sciences. 112: 201423555. doi:10.1073/pnas.1423555112. PMC 4371906. PMID 25675512.