An efficient, one-pot synthesis of various ceramide 1-phosphates from sphingosine 1-phosphate.
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.
Nussbaumer
Peter
P
Novartis Institutes for BioMedical Research, Brunner Strasse 59, A-1235 Vienna, Austria. peter.nussbaumer@novartis.com
Hornillos
Valentin
V
Ghobrial
Michael
M
Ullrich
Thomas
T
D002518:Ceramides / Q000138:chemical synthesis* / Q000737:chemistry; D008246:Lysophospholipids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
D002518:Ceramides; D008246:Lysophospholipids; C065576:ceramide 1-phosphate; C060506:sphingosine 1-phosphate; D013110:Sphingosine