Add time:07/24/2019         Source:sciencedirect.com

Publisher SummarySphingosine is the major lipid moiety of glycosphingolipids and phosphosphingolipids (sphingomyelins, glycosylphosphatidylinositols). These compounds are expressed on the surface of cell membranes and they play an important role in cell-cell interactions, in signal transduction, and in the anchoring of proteins. Sphingosine was found to have regulatory properties, and it is of importance as an inhibitor of protein kinase C. Because of the large variety of sphingosine moieties found in natural sources and the requirement of labeled and modified sphingosine derivatives for biological and pharmacological investigations, efficient chemical syntheses are of great importance. The synthesis of some 1-amino derivatives of sphingosine is described. The readily accessible azidosphingosine is converted into its 1-O-mesyl derivative. By reaction with morpholine, pyrrolidine, and sodium azide the 1-morpholino and 1-pyrrolidino derivatives of azidosphingosine, as well as 1,2-diazidosphingosine, are obtained. Reduction with hydrogen sulfide in the usual way yields 1-morpholino-1-deoxy-, 1-pyrrolidino-1-deoxy-, and 1-amino-1-deoxysphingosine, the latter by means of benzoyl protection of the 3-OH group. The influence of 1-morpholino and other derivatives of sphingosine on melanoma cell motility and growth have been investigated, and the 1-pyrrolidino derivative of sphingosine is a potent inhibitor of fucosyltransferase, which is involved in glycoprotein synthesis.

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