Sphingosine configuration, determination

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. 

The anomeric configuration of the D-galactopyranosyl group on the sphingosine moiety was determined by the degradation method of... 

The diastereoisomeric configuration of the sugar-free cerebrosides (ceramides) was determined by Carter and coworkers,80 and found to be erythro, in accordance with the structure of sphingosine, which is isolated after drastic hydrolysis of sphingolipid mixtures or purified cerebrosides with acid. 

The configuration of the sphingosine formed during incubations of serine-C and palmityl-SCoA with rat brain homogenates was determined by Fujino and Zabin (1962a,b). In these experiments, carrier eri/ Aro-sphingosine and carrier... 

Table 6. Determinations of the configuration (threo or erythro) of sphingosine in sphingomyelin...

Ichihashi, M. and Mori, K. (2003) Determination of the absolute configuration of (+)-xestoaminol C, (2S,3R)-2-amino-3-tetradecanol, a metabolite of Eiji sponge, Xe stospongia sp., by the synthesis of its N, Odiacetyl derivative. Biosci. Biotechnol. Biochem., 67, 329-333. Abraham, E., Davies, S.G., Millican, N.L., Nicholson, R.L., Roberts, P. M., and Smith, A.D. (2008) Asymmetric synthesis of vicinal amino alcohols xestoaminol C, sphinganine and sphingosine. Org. Biomol. Chem., 6,1655—1664. 

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