Phosphono-sphingomyelins. I: Synthesis of ceramide (trimethyl) aminoethyl phosphonate |
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Authors: | Vassilios M. Kapoulas Michael C. Moschidis |
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Affiliation: | Department of Biochemistry, School of Natural Sciences, University of Ioannina, Ioannina Greece |
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Abstract: | The synthesis of the phosphono-analogue of sphingomyelin is described. The N-acyl-D-erythro-sphingosyl-1-(N,N,N-trimethyl-2-aminoethyl) phosphonate was obtained by phosphonylation of N-acyl-3-O-benzoyl-D-erythro-sphingosine with (2-bromoethyl)phosphonic acid chloride and triethylamine, subsequent quaternisation with anhydrous trimethylamine and benzene at 55–60°C for four days, and finally, consecutive removal of the protective group by mild alkaline hydrolysis. Comparison of the CD spectra of both, natural sphingomyelin and its phosphono-analogue, confirmed that their structures and configurations were identical. |
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