Nussbaumer, Peter, Hornillos Gomez-Recuero, Valentin, Ghobrial, Michael and Ullrich, Thomas (2008) An efficient, one-pot synthesis of various ceramide 1-phosphates from sphingosine 1-phosphate. Chemistry and Physics of Lipids, 151 (2). pp. 125-128. ISSN 0009-3084

Abstract

An efficient, one-pot procedure for the synthesis of ceramide 1-phosphates with varying N-acyl substituents, to serve as tool compounds for analytical and biological investigations, was developed. Sphingosine 1-phosphate was silylated in situ to increase its solubility and to protect the 3-hydroxy functionality and then allowed to react with activated acid derivatives in the presence of diisopropylethylamine. Simultaneous cleavage of the silyl protecting groups and separation from reagents and by-products was achieved by medium pressure chromatography on reversed phase material. Thus, ceramide 1-phosphates with various fatty acid chains and with fluorescent and affinity labels attached to the sphingoid backbone were prepared in good yields.

Item Type:	Article
Related URLs:	http://www.ncbi.nlm.nih.gov/sites/entrez... doi:10.1016/j.chemphyslip.2007.10.005
Additional Information:	author can archive post-print (ie final draft post-refereeing); Publisher's version/PDF cannot be used
Keywords:	Biotin; Ceramide phosphate; Fluorescence; Sphingosine phosphate; Sphingolipids; Sphingolipidomics
Related URLs:	http://www.ncbi.nlm.nih.gov/sites/entrez... doi:10.1016/j.chemphyslip.2007.10.005
Date Deposited:	14 Dec 2009 14:01
Last Modified:	14 Dec 2009 14:01
URI:	https://oak.novartis.com/id/eprint/344