A simple method for the synthesis of ceramides and radiolabeled analogues.
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.
Anand
J K
JK
Biomembrane Institute, Seattle, Washington 98119-4237, USA.
Sadozai
K K
KK
Hakomori
S
S
D002518:Ceramides / Q000138:chemical synthesis*; D002855:Chromatography, Thin Layer; D009682:Magnetic Resonance Spectroscopy; D011868:Radioisotopes; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013237:Stereoisomerism
D002518:Ceramides; D011868:Radioisotopes