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We have synthesized, beside the presently consecrated stress molecule,  b-D-glucopyranosyl-cholesterol, b-D-arabinopyranosyl-, a-L-arabinofuranosyl- and b- and a-D-(3-O-methyl)glucopyranosyl-cholesterol. Two types of glycosylation agents were used: peracylated sugar bromide, with CdCO3 as promotor, and peracetylated sugar in the presence of BF3OBu2 as promoting agent, respectively. A chemical test was used for synthesis monitoring: Zempln saponification of reaction mixture had to produce an amphiphilic glycoside migrating in the region of cerebrosides, by TLC in a suitable solvent system. All intermediates and final products have been characterized by 1H and 13C NMR spectroscopy as well as by chemical and chromatographical methods. In the virtue of the recently discovered biochemical relationships of cholesterol and cerebrosides (or glycosterols and ceramide) new biochemical hypotheses have been advanced concerning the meaning of these new glycosides.

revista de chimie

Alternate Modulation of Biological Activity of Stress Molecule, b-D-glucopyranosyl-cholesterol, by Chemical Modification of Sugar Moiety. Hypotheses concerning biochemical meaning of the new glycosides