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A simple method for the synthesis of ceramides and radiolabeled analogues

1996; Wiley; Volume: 31; Issue: 9 Linguagem: Inglês

10.1007/bf02522695

1558-9307

Jasbir K. Anand, Khalid Khan Sadozai, Sen‐itiroh Hakomori,

Marine Toxins and Detection Methods

A simple method has been developed for the coupling of amines to carboxylic acids. N-Fatty-acyl-sphingosine, cerebroside, and GM3, as well as their respective [14C] 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 [3H]-N-acyl-labeled, as well as [14C] [3H] double-labeled, ceramides.