A SIMPLE METHOD FOR THE SYNTHESIS OF CERAMIDES AND RADIOLABELED ANALOGUES

摘要

A simple method has been developed for the coupling of amines to carboxylic acids. N-Fatty-acyl-sphingosine, cerebroside, and GM(3), as well as their respective [C-14] analogues, were synthesized using diethylphosphoryl cyanide as a potent coupling agent in the presence of triethylamine. The reaction procedure is rapid, racemization-free, and utilizes acids without derivatization. The desired ceramide products were obtained in 85-90% yield within one hour. The facile method presented here can also be used to synthesize [H-3]-N-acyl-labeled, as well as [C-14] [H-3] double-labeled, ceramides. [References: 24]