The total syntheses of D-erythro-sphingosine, N-palmitoylsphingosine (ceramide), and glucosylceramide (cerebroside) via an azidosphingosine analog.
The total synthesis of D-erythro-sphingosine (9) was performed by a chirospecific method starting from D-galactose via an azidosphingosine intermediate to give highly homogeneous (>99.9% C18:1) sphingosine base (9) which contained no observable olefin isomerization by product and was demonstrated to be optically pure by a novel method utilizing Mosher's acid. Ceramide (10) was prepared from this sphingosine (9) with highly homogeneous (99.8% C16:0) palmitic acid by two methods. The cerebroside glucosylceramide (23) was the next sphingolipid in this series to be synthesized in a highly homogeneous form. These three sphingolipids are currently being used for biophysical studies of the structures of their hydrated bio-molecular assemblies.
Duclos
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Department of Physiology and Biophysics, Boston University School of Medicine, 715 Albany Street, 02118-2526, Boston, MA, USA. duclos@med-biophd.bu.edu
D002518:Ceramides / Q000138:chemical synthesis* / Q000737:chemistry; D005963:Glucosylceramides / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008722:Methods; D013110:Sphingosine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D002518:Ceramides; D005963:Glucosylceramides; C097760:N-palmitoylsphingosine; D013110:Sphingosine