Glycosphingolipids moiety

Gangliosides are a class of glycosphingolipid characterized by the presence of one or more sialic acid residues. They are located in the cell membranes, particularly in the plasma membrane, of almost all cell types. They are anchored in the membranes through their ceramide moiety and have the polar sugar-containing group in the extracytoplasmic side. They are particularly abundant in the nervous system where their expression pattern is modulated during development. 

It is extremely difficult to maintain uniform nomenclature or abbreviations for these molecules due to the diverse nature of the saccharide moiety and the continual discovery of new glycosphingolipids. A semi-systematic nomenclature for glycosphingolipids has been recommended by the IUPAC-IUB Commission on Biochemical Nomenclature,7 and has been reviewed in some detail.8-10 Readers are urged to consult these articles in order to become familiar with the no-... 

The glycosphingolipids of mammals are known to be cellular-membrane components,1"5 organized in such a way that their lipid moiety, namely, acylated sphingosine (usually called ceramide), is submerged into the outer leaflet of the plasma-membrane bilayer, and contributes to its structural... 

The procedure of isolating the glycosphingolipids is based on their physicochemical properties. The presence of the lipophilic, lipid moiety results in their solubility in such typical solvents for lipids as chloroform-methanol. On the other hand, the presence of the carbohydrate moiety imparts to them hydrophilic properties that increase with increase in the length of the carbohydrate chain and with the presence of such polar monosaccharides as sialic acid. This very property makes it possible to subdivide the glycolipids further, according to their polarity. In principle, the isolation of glycosphingolipids from marine animals does not differ from their isolation from other sources, a procedure comprehensively elucidated in a number of reviews.80 88... 

Structural studies of glycosphingolipids involves determination of the structure of the oligosaccharide chain and of the lipid moiety. For the oligosaccharide chain, it is necessary to determine the composition, molar ratio, and sequence of the monosaccharides, their pyranose or furanose nature, and the position of glycosidic bonds and their configuration for the lipid moiety, the composition of the fatty acids and sphingosine bases must be determined. Used for these purposes are the classical, chemical methods, conventionally accepted in the chemistry of carbohydrates and lipids and based on the degradation of compounds, enzymic, and physicochemical methods, primarily mass spectrometry and n.m.r. spectroscopy. 

To determine the position of glycosidic bonds in glycosphingolipids, periodate oxidation and methylation are widely used. A characteristic feature of the periodate oxidation of glycosphingolipids is the stability, to oxidation under mild conditions,179 of the D-glucose residue that is located at the beginning of the carbohydrate chain and substituted at 0-4 this seems to be associated with steric hindrance caused by the close location of the lipid moiety. 

In contrast to the striking divergences in the carbohydrate parts, respective ceramide moieties resemble those of other cestode glycosphingolipids in so far as sphinganine (d18 0) and 4-hydroxy-sphingoid bases (tl 8 0, t20 0) as well as, in part hydroxylated, fatty acids with 16 to 28 carbon atoms, in particular C26 0 and C28 0, represent predominant ceramide constituents, which might be an indication of similar biosynthetic routes. 

Incorporation of tritium (cpm/mg of protein) into individual moieties of glycosphingolipids of normal human skin fibroblasts in the presence and absence of galactose oxidase... 

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