Literature DB >> 8882981

A simple method for the synthesis of ceramides and radiolabeled analogues.

J K Anand1, K K Sadozai, S Hakomori.   

Abstract

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.

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Year:  1996        PMID： 8882981     DOI： 10.1007/bf02522695

Source DB:  PubMed          Journal:  Lipids        ISSN： 0024-4201            Impact factor:   1.880


  11 in total

1.  N-Ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline, a new inhibitor of the mitochondrial F1-ATPase.

Authors:  R Pougeois; M Satre; P V Vignais
Journal:  Biochemistry       Date:  1978-07-25       Impact factor: 3.162

2.  Ceramide glycanase from rat mammary tissues: inhibition by PPMP(D-/L-) and its probable role in signal transduction.

Authors:  M Basu; M Girzadas; S Dastgheib; J Baker; F Rossi; N S Radin; S Basu
Journal:  Indian J Biochem Biophys       Date:  1997 Feb-Apr       Impact factor: 1.918

3.  Preparative isolation of cerebrosides (galactosyl and glucosyl ceramide).

Authors:  N S Radin
Journal:  J Lipid Res       Date:  1976-05       Impact factor: 5.922

4.  Preparation of psychosines (1-O-hexosyl sphingosine) from cerebrosides.

Authors:  N S Radin
Journal:  Lipids       Date:  1974-05       Impact factor: 1.880

5.  A new convenient reagent for peptide syntheses.

Authors:  B Belleau; G Malek
Journal:  J Am Chem Soc       Date:  1968-03-13       Impact factor: 15.419

Review 6.  The sphingomyelin pathway in tumor necrosis factor and interleukin-1 signaling.

Authors:  R Kolesnick; D W Golde
Journal:  Cell       Date:  1994-05-06       Impact factor: 41.582

Review 7.  The sphingomyelin cycle and the second messenger function of ceramide.

Authors:  Y A Hannun
Journal:  J Biol Chem       Date:  1994-02-04       Impact factor: 5.157

8.  Letter: Diphenyl phosphorazidate (DPPA) and diethyl phosphorocyanidate (DEPC). Two new reagents for solid-phase peptide synthesis and their application to the synthesis of porcine motilin.

Authors:  S I Yamada; N Ikota; T Shioiri; S Tachibana
Journal:  J Am Chem Soc       Date:  1975-11-26       Impact factor: 15.419

9.  Short chain ceramides as substrates for glucocerebroside synthetase. Differences between liver and brain enzymes.

Authors:  R R Vunnam; N S Radin
Journal:  Biochim Biophys Acta       Date:  1979-04-27

10.  Synthesis of O-glycopyranosyl-N-hydroxysuccinimides of glucose and lactose and their opening by nucleophiles into prespacer glycosides.

Authors:  M Andersson; S Oscarson
Journal:  Glycoconj J       Date:  1992-06       Impact factor: 2.916
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  2 in total

1.  The mitochondria-associated endoplasmic-reticulum subcompartment (MAM fraction) of rat liver contains highly active sphingolipid-specific glycosyltransferases.

Authors:  Dominique Ardail; Iuliana Popa; Jacques Bodennec; Pierre Louisot; Daniel Schmitt; Jacques Portoukalian
Journal:  Biochem J       Date:  2003-05-01       Impact factor: 3.857

2.  Chemical and enzymatic transacylation of amide-linked FA of buttermilk gangliosides.

Authors:  Christopher Beermann; Anne-Katrin Röhrig; Günther Boehm
Journal:  Lipids       Date:  2003-08       Impact factor: 1.880
  2 in total

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