Synthesis of spacer-arm, lipid, and ethyl glycosides of the trisaccharide portion [alpha-D-Gal-(1----4)-beta-D-Gal-(1----4)-beta-D-Glc] of the blood-group Pk antigen: preparation of neoglycoproteins.
The title compounds were prepared via the acetylated 2-bromoethyl glycoside 11 of alpha-D-Gal-(1----4)-beta-D-Gal-(1----4)-beta-D-Glc by displacement of bromide ion with methyl 3- mercaptopropionate , octadecanethiol , and hydrogen, respectively. Silver triflate -promoted glycosylation of 2-bromoethyl 2,3,6-tri-O-benzyl-beta-D-glucopyranoside with 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl) -alpha -D-galactopyranosyl bromide gave 11. A tetradeuterated analogue of 11 was prepared by essentially the same route. The spacer-arm glycoside formed from methyl 3- mercaptopropionate was coupled to bovine serum albumin and keyhole limpet haemocyanin.
D001789:Blood Group Antigens; D005915:Globosides / Q000138:chemical synthesis*; D006023:Glycoproteins / Q000138:chemical synthesis*; D006028:Glycosphingolipids / Q000138:chemical synthesis*; D006801:Humans; D014281:Trihexosylceramides
D001789:Blood Group Antigens; D005915:Globosides; D006023:Glycoproteins; D006028:Glycosphingolipids; D014281:Trihexosylceramides; C018549:globotriaosylceramide