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(2 S,3 R,E)-3-((3-carboxypropanoyl)oxy)-2-palmitamidooctadec-4-en-1-yl (2-(trimethylammonio)ethyl) phosphate (SM-COOH)

ZW Zhiren Wang
WL Wenpan Li
YJ Yanhao Jiang
TT Tuyen Ba Tran
LC Leyla Estrella Cordova
JC Jinha Chung
MK Minhyeok Kim
GW Georg Wondrak
JE Jennifer Erdrich
JL Jianqin Lu
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The synthesis of SM-COOH was according to our previous publication39. 4-pyrrolidinopyridine (4-PPY, 148 mg, 1 mmol) was added to a solution of sphingomyelin (8.01 g, 10.0 mmol) and succinic anhydride (10 g, 100 mmol) in anhydrous CHCl3 (200 mL). The solution was stirred at room temperature and monitored by TLC (developing solvent: CHCl3/EtOH/H2O (v/v/v, 300/200/36) with one drop of concentrated NH3·H2O). After completion of the reaction, CH3OH (50 mL) was added into the mixture solution, the reaction was further stirred at room temperature for 12 h. The solvent was evaporated using rotary evaporator under vacuum, and the residue was purified by silica gel flash chromatography with CHCl3/EtOH/H2O (v/v/v, 300/200/36) as the elution solvent. White solid with 95% yield was achieved.

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