Sphingolipids long-chain bases

Karlsson, K.-A. (1970) Sphingolipid long chain bases, Lipids 5, 878-889. 

Karlsson KA, Samuelsson BE, Steen GO (1968) Structure and function of sphi-nolipids. 1. Differences in sphingolipid long-chain base pattern between kidney cortex, medulla, and papillae. Acta Chem Scand 22 1361-1364... 

Karlsson, K.-A. 1970. On the chemistry and occurrence of sphingolipid long-chain bases. Lipids 5 6-43. Goni, F.M., Alonso, A. 2006. Biophysics of sphingolipids. I. Membrane properties of sphingosine, ceramides and other simple sphingolipids. Biochim. Biophys. Acta 1758 1902-1921. 

Karlsson, K.A., On the chemistry and occurrence of sphingolipid long-chain bases, Chem. Phys. Lipids, 5, 6-43, 1970. 

Lynch DV, Fairfield SR. Sphingolipid long-chain base synthesis in plants characterization of serine palmitoyltransferase activity in squash fruit microsomes. PI Physiol 1993 103 1421-1429. 

Morrison, W. R. 1973. Long-chain bases in the sphingolipids of bovine milk and kidney, rumen bacteria, rumen protozoa, hay and concentrate. Biochim. Biophys. Acta 316, 98-107. 

Morrison, W. R. and Hay, J. D. 1970. Polar lipids in bovine milk. II. Long-chain bases, normal and 2-hydroxy fatty acids, and isomeric cis and trans monoenoic fatty acids in the sphingolipids. Biochim. Biophys. Acta 202, 460-467. 

The backbone structure of the sphingolipids found in mammalian cells is the long-chain base, sphingosine. The latter is an 18-carbon moiety comprised of an aminoethanol residue at C-l (OH) and C-2 (NH2) with an allylic hydroxyl at C-3. Another name for sphingosine is D-erythro-2-amino-octadec-4-ene-l,3-diol. The latter compound is often referred to as sphingenine by many investigators. 

Carter HE, Clemer WD, Lands WM, Muller KL, Tomizawa HH (1954) Biochemistry of the sphingolipides. VIII. Occurrence of a long chain base in plant phosphatides. J Biol Chem 206 613-623 Casiraghi G, Rassu G, Spanu P (1995) Stereoselective approaches to bioactive carbohydrates and alkaloids-with a focus on recent syntheses drawing from the chiral pool. Chem Rev 95 1677... 

Inositolphosphoryl ceramide-type sphingolipids were isolated from hyphal forms of C. albicans and three classes of molecules were fractionated by preparative HPLC on silica gel [65], Molecular species in each class differ in the composition of long chain bases and fatty acids the most abundant long chain bases were Cl8 and C20 phytosphingosines, while hydroxy and non-hydroxy C24, C25 and C26 were the most abundant fatty acids. The proposed structures, Ins-P-Cer, Man-Ins- P-Cer and Ins-P-Man-Ins-P-Cer, closely resemble the sphingolipids identified in S. cerevisiae [53],... 

Figure 12.16 Sphingolipid biosynthesis in Pichia ciferrii. Enzymes are shown as ovals and named according to the corresponding homologues from Saccharomyces cerevisiae. Abbreviations AcTR, acetyl-CoA long-chain base acetyltransferase TAPS, tetraacetyl phytosphingosine TriASa, triacetyl sphinganine TriASo, triacetyl sphingosine IP, inositol phosphoryl. TAPS is by far the most abundant sphingolipid formed in wild-t5 e cells, as reflected by the strength of the arrows.

Analysis of sphingolipids requires degradative procedures. Methods for the analysis of the long-chain bases have been reviewed (Karlsson, 1970a). 

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