Ninhydrin → HCID 178418600, compound

Participants

Reaction Steps

75 mg (0.101 mmol) of dioleoylphosphatidylethanolamine (Avanti Polar Lipids, USA) (DOPE), 34.3 mg (0.110 mmol) of Nalpha -tret-butoxycarbonyl-arginine hydrochloride (Sigma, USA), 24.8 mg (0.129 mmol) of N-ethyl-N'-dimethylaminopropyl-carbodiimide hydrochloride (Sigma, USA), and 14.9 mg (0.129 mmol) of N-hydroxysuccinimide (Sigma, UAS) were dissolved in 2 ml of chloroform and incubated with agitation at 37° C. for 3 hours. At that point, TLC (CHCl3 --CH3OH--H2 65:25:4, silica) showed 100% conversion of DOPE (Rf 0.49) into faster moving, ninhydrin-negative product (Rf 0.69), identified as N-(Nalpha -tret-butoxycarbonyl-arginyl)-DOPE. This product was purified by chromatography on silica and deprotected by treatment with 4M HCl in anhydrous dioxane for 3 hours. After removal of volatiles in vacuum, the residue was chromatographed on silica, eluent CHCl3 --CH3OH 7:3, to obtain Arg-PE (Rf 0.26 in the above system) with the yield of 10.8 mg (12% of theory). Phosphate to primary amino group ratio: Theory 1.0, Found 0.90±0.12.

Provenance & Evidence