Synthesis from Pullulan of Spacer-arm, Lipid, and Ethyl Glycosides of a Tetrasaccharide [alpha-D-Glc-(1----6)-alpha-D-Glc-(1----4)-alpha-D-Glc-(1----4)-D-Glc] Found in Human Urine; Preparation of Neoglycoproteins

Enzymic hydrolysis of pullulan, followed by acetylation and chromatography, gave acetylated alpha-D-Glcp-(1----6)-alpha-D-Glcp-(1----4)-alpha-D-Glcp-(1----4)-D-Glcp which, with 2-bromoethanol and boron trifluoride etherate in dichloromethane, gave the 2-bromoethyl glycoside. The reactions of the glycoside with methyl 3- mercaptopropionate , methyl 11- mercaptoundecanoate , and octadecanethiol are described, and also its hydrogenolysis to give an ethyl glycoside. The mercaptopropionate -derived, spacer-arm glycoside has been coupled to bovine serum albumin and keyhole limpet haemocyanin.