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An efficient, one-pot synthesis of various ceramide 1-phosphates from sphingosine 1-phosphate.

Nussbaumer, Peter and Hornillos, Valentin and 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
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Date Deposited: 14 Dec 2009 14:04
Last Modified: 14 Dec 2009 14:04
URI: https://oak.novartis.com/id/eprint/185

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