S. F. Perez, R. G. Lio, V. F. Santana
Aug 1, 1998
Citations
0
Influential Citations
5
Citations
Journal
Journal of Carbohydrate Chemistry
Abstract
Abstract 5-Azido-3-oxa-l-pentanol was prepared from 2-(2-chloroethoxy)ethanol and used as a spacer in the chemical synthesis of the trisaccharide β-D-Gal-(1→4)-[α-L-Fuc-(1→3)]-GlcNAc and the tetrasaccharide α-L-Fuc-α-(1→2)-β-D-Gal-(1→4)-[α-L-Fuc-(1→3)]-GlcNAc that represent the epitopes defining the human blood groups Lex and Ley. The classical 4-methoxybenzyl group and the remarably acid-stable 3-methoxybenzyl group were compared as temporary protective groups for position 3 at the glucosamine unit to circumvent the problems associated with the simultaneous presence of allyl and azido groups. The resulting oligosaccharides were coupled to proteins with high efficiency. 1 Presented at the VII European Curbohydrate Syposium, Cracow, Poland, August 22–27, 1993.