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Secologanin

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Secologanin
Names
IUPAC name
Methyl (2S,3R,4S)-3-ethenyl-2-(β-D-glucopyranosyloxy)-4-(2-oxoethyl)-3,4-dihydro-2H-pyran-5-carboxylate
Systematic IUPAC name
Methyl (4S,5R,6S)-3-ethenyl-4-(2-oxoethyl)-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
UNII
  • InChI=1S/C17H24O10/c1-3-8-9(4-5-18)10(15(23)24-2)7-25-16(8)27-17-14(22)13(21)12(20)11(6-19)26-17/h3,5,7-9,11-14,16-17,19-22H,1,4,6H2,2H3/t8-,9+,11-,12-,13+,14-,16+,17+/m1/s1 InChI Key = CSKKDSFETGLMSB-NRZPKYKESA-N
  • COC(=O)C1=CO[C@H]([C@@H]([C@@H]1CC=O)C=C)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
Properties
C17H24O10
Molar mass 388.369 g·mol−1
Density 1.42 g/mL
Boiling point 595.5 °C (1,103.9 °F; 868.6 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Secologanin is a secoiridoid monoterpene synthesized from geranyl pyrophosphate in the mevalonate pathway. Secologanin then proceeds with dopamine or tryptamine to form ipecac and terpene indole alkaloids, respectively.

Biosynthesis

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Secologanin biosynthesis begins from geranyl pyrophosphate (GPP) taken from the mevalonate pathway used to make terpenoids. Recent efforts have characterized the entire secologanin biosynthetic pathway.[1] Secologanin is formed from loganin through the action of the enzyme secologanin synthase. Secologanin is then able to proceed onto produce ipecac and terpene indole alkaloids.[2]

References

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  1. ^ Miettinen K, Dong L, Navrot N, Schneider T, Burlat V, Pollier J, et al. (April 2014). "The seco-iridoid pathway from Catharanthus roseus". Nature Communications. 5 (1): 3606. doi:10.1038/ncomms4606. PMC 3992524. PMID 24710322.
  2. ^ "Secologanin Biosynthesis". Nomenclature Committee of the International Union of Biochemistry and Molecular Biology (NC-IUBMB). Retrieved 31 May 2011 – via School of Physical and Chemical Sciences, Queen Mary University of London.