A concise synthesis of the A and B blood group antigenic determinants

Novel and concise synthetic routes to the trisaccharide A and B blood group antigenic determinants have been devised. These trisaccharides, each containing a d-galactosyl-based and l-fucosyl moiety both α-linked to a central d-galactose unit, have previously been synthesised via a variety of methods, with most reporting poor yields. Developments in carbohydrate synthesis, especially the availability of highly α-selective galactosyl donors, provided the opportunity for novel and robust syntheses of these biologically relevant antigenic determinants to be explored. Herein are demonstrated efficient routes to these blood group antigenic determinants via initial establishment of the key α-1,3 linkage, followed by a late-stage incorporation of the l-fucosyl unit. These synthetic routes have the potential to be utilised in the preparation of similar compounds, with applications in ongoing research into the ABO blood group antigens and their influence on human health and disease states.