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A simple method for the synthesis of ceramides and radiolabeled analogues
Author(s) -
Anand Jasbir K.,
Sadozai Khalid K.,
Hakomori Senitiroh
Publication year - 1996
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/bf02522695
Subject(s) - racemization , derivatization , sphingosine , cerebroside , chemistry , ceramide , triethylamine , yield (engineering) , chromatography , cyanide , acylation , organic chemistry , combinatorial chemistry , biochemistry , high performance liquid chromatography , catalysis , apoptosis , materials science , receptor , metallurgy
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 [ 14 C] 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 [ 3 H]‐ N ‐acyl‐labeled, as well as [ 14 C] [ 3 H] double‐labeled, ceramides.
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