A simple method for the synthesis of ceramides and radiolabeled analogues

Lipids - Tập 31 Số 9 - Trang 995-998 - 1996
Jasbir K. Anand1, Khalid Khan Sadozai1, Sen‐itiroh Hakomori1
1The Biomembrane Institute, Seattle

Tóm tắt

AbstractA 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.

Từ khóa


Tài liệu tham khảo

Hakomori S., 1983, Handbook of Lipid Research, 1

10.1016/S0021-9258(17)41834-5

10.1016/0092-8674(94)90147-3

Basu M., 1995, Ceramide Glycanase from Rat Mammary Tissue, Glycoconjugate J., 12, 439

Basu M. Girzadas M. Dastgheib S. Baker J. Rossi F. Radin N.S. andBasu S.(1996)Ceramide Glycanase from Rat Mammary Tissue; Inhibition by PPMP (D/L‐) and Its Probable Role in Signal Transduction Indian J. Biochem. Biophys.33 in press.

10.1080/07328308908048004

10.1016/0006-291X(74)91016-X

10.1080/07328308808058935

10.1016/0005-2760(79)90174-7

10.1021/ja00902a047

10.1007/BF00780758

10.1111/j.1749-6632.1960.tb20059.x

Neises B. Andries T. andSteglich W.(1982)Racemisation‐Free Esterification of 2‐Nitrophenylsulphenyl‐Protected Amino Acids by Dicyclohexylcarbodi‐Imide‐4‐Dimethylaminopyridine J. Chem. Soc. Chem. Commun. 1132–1133.

10.1021/ja01008a045

10.1016/0008-6215(86)84009-5

10.1021/ja00857a042

10.1021/bi00608a013

10.1002/hlca.19880710208

10.1002/jlcr.2580290508

10.1007/BF02533114

10.1016/S0022-2275(20)36989-3

10.1016/0008-6215(89)84060-1

10.1016/S0040-4039(01)96005-8

10.1016/0040-4020(76)85134-4

Thông tin
Thông tin xuất bản

Lipids

Tập 31 Số 9

995-998

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