A short chemo-enzymic route to glycosphingolipids using soluble glycosyl transferases

Abstract

Two commercially available soluble glycosyl transferases, a β-1,4-galactosyl transferase from bovine milk and an α-2,6-sialyl transferase from rat liver, were used for the synthesis of several glycosphingolipids. The synthetic strategy involves the chemical synthesis of 2-azido- and 2-amino-sphingosine glycosides (5, 6, 10 and 11) and further glycosylation of their sugar headgroups to complex glycolipids. The azido- or amino-sphingosine lipid sidechain can then be further elaborated by reduction and/or acylation.