THE CHEMICAL SYNTHESIS AND PHYSICAL CHARACTERIZATION OF 1,2-DI-O-ACYL-3-O-(ALPHA-D-GLUCOPYRANOSYL)-SN-GLYCEROLS, AN IMPORTANT CLASS OF MEMBRANE GLYCOLIPIDS

Improved procedures for the preparation of 1,2-di-O-acyl-3-O-(α-d-glucopyranosyl)-sn-glycerols have been developed. The procedures are based on a halide ion condensation of a benzylated 1-bromo sugar with 1,2-di-O-butenyl-sn-glycerol and have enabled a relatively straightforward and inexpensive synthesis of 1,2-di-O-acyl-3-O-(α-d-Glucopyranosyl- and 1,2-di-O-acyl-3-O- d-galactopyranosyl)-sn-glcerols with a wide variety of acyl chain lengths and structure and in quantities suitable for detailed structural studies. The analytical data on these compounds are consistent with the expected structure and high sample purity. A physical characterization of the α-D-glycosyl diacylglycerols also indicates that the solid phase and solution properties of these glucolipids differ markedly from those previously reported for the β-anomers. Such differences should also be manifest in the polymorphic phase behavior of lipid bilayers composed of these lipids. © 1990.