SYNTHESIS OF GLYCOLIPIDS CONTAINING DISACCHARIDES AND 2 LONGER ALKYL CHAINS AND THEIR APPLICATIONS AS ENZYME MODIFIERS

The aminolysis between p-(aminomethyl)benzoic acid and lactobiono-1,5- lactone was carried out in Me(2)SO in quantitative yield. The amide fo rmed thus was used directly for the final reaction without isolation o f the intermediate from the reaction mixture, This simple one-pot proc edure finished a convenient and useful synthesis of the target alkyl-L -glutamatecarbonyl)-benzyl]lactobionamides. The phase-transition tempe rature of glycolipids was shown to greatly depend on the structure bet ween the hydrophilic moiety and the hydrophobic segment of the glycoli pids, The yield of proteins of lipases coated with the glycolipids con taining disaccharides remarkably increased with alkyl-chain length, wh ich was higher than that with glycolipids containing monosaccharides. The yields were also closely correlated to the origin of the lipases. The enzymatic reactivity of lipid-coated lipase PS was seldom affected by the hydrophobic segment of lipids, but its enantioselectivity was mainly affected by the hydrophilic moiety of lipids. (C) 1996 Elsevier Science Ltd.