Synthesis of octyl O- and S-glycosides related to the GPI anchor of Trypanosoma brucei and their in vitro galactosylation by trypanosomal α-galactosyltransferases

Abstract

Octyl O- and S-glycosides of mono- to tri-saccharides related to the core structure α-d- Manp-(1 a ̊ 2)-α-d- Manp-(1 a ̊ 6)-α-d- Manp of the GPI anchor of Trypanosoma brucei have been prepared via regioselective protodesilylation and glycodesilylation of octyl O- and S-glycosides of 2- O-benzoyl-4,6- O-(1,1,3,3-tetraisopropyl-1,3-disiloxane-1,3-diyl)- α- d-mannopyranoside. The synthetic saccharides have been used as substrates for enzymatic α-galactosylation with membrane fractions of bloodstream forms of T. brucei strain 427 variants MITat 1.4, MITat 1.2, and MITat 1.5, respectively.