セコロガニン

セコロガニン (Secologanin) is monoterpene composed by geranyl pyrophosphoric acid in a mevalonate course. セコロガニン produces Ipecac alkaloids with dopamine more.

セコロガニン
IUPAC name Methyl (2S,3R,4S) -3-ethenyl-2-(β-D-glucopyranosyloxy) -4-(2-oxoethyl) -3,4-dihydro-2H-pyran-5-carboxylate
Identification information
CAS registration number	19,351-63-4
PubChem	161276
ChemSpider	141670
SMILES 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
InChI InChI=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
Characteristic
Chemical formula	C17H24O10
Molar mass	388.37 g mol-1
Density	1.42 g/mL
The boiling point	595.5 ° C, 869 K, 1,104 degrees Fahrenheit
I can put a case, the data without the special mention for normal temperature (25 degrees Celsius), the ordinary pressure (100 kPa).

Biosynthesis

The セコロガニン biosynthesis begins in the place where the geranyl pyrophosphoric acid of the mevalonate course origin forms 7-デオキシロガナート or 7-デオキシロガニン by an undetermined enzyme. 7-デオキシロガナート and 7-デオキシロガニン generate ロガナート and ロガニン in response to NADPH by an enzyme each afterwards. I can convert ロガナート into ロガニン using S-adenosylmethionine (SAM). ロガナート and ロガニン form セコロガナート and セコロガニン by the reaction with the enzyme more afterwards. セコロガナート becomes セコロガニン in response to SAM of another 1 molecules. セコロガニン becomes the biosynthesis materials of Ipecac alkaloids [¹].

 

Biosynthesis of セコロガニン

Source

1. ^ "Secologanin Biosynthesis." May 31, 2011 reading.

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