BIOCHEMISTRY OF THE SPHINGOLIPIDES

Abstract

Sphingosine was discovered by Thudichum (2, 3), who isolated it from the hydrolysis products of phrenosin, characterized it as a base of empirical composition C~'IH~~NO~, and described a number of its salts.Wiirner and Thierfelder (4) reported that sphingosine absorbed bromine, indicat'ing unsaturation in the molecule.Several years later, Levene and Jacobs (5) in a more thorough study characterized sphingosine as an unsaturated monoaminodihydroxy alcohol.They prepared a triacetyl derivative (m.p. 102-103") and reduced sphingosine to dihydrosphingosine with palladium as the catalyst.In the same year Thomas and Thierfelder (6) also reported the preparation of triacetylsphingosine (m.p. 100-1020).Lapworth (7) and Levene and West (8, 9) oxidized sphingosine with chromic acid and obtained an acid which was identified as n-tridecanoic acid, although its melting point did not agree too well with that of an authentic sample.Levene and West also oxidized dihydrosphingosine in a similar fashion and obtained an acid melting at GO-61°, which they identified as n-pentadecanoic acid.These results indicate that sphingosine has a Cl, straight chain with a double bond between carbon atoms 4 and 5, and with two hydroxyl groups and an amino group on the first 3 carbon atoms.Levene and West (9) also investigated the ozonolysis of sphingosine.The nitrogen-containing fragment was oxidized further with nitric acid to a substance tentatively identi-