Synthesis of azido-deoxy and amino-deoxy glycosides and glycosyl fluorides for screening of glycosidase libraries and assembly of substituted glycosides

Abstract

Azide- and amine-substituted sugars can be useful tools in the probing of biological systems as well as in the assembly of libraries of derivatives using click chemistry or simple amine coupling approaches. A collection of methylumbelliferyl glycosides of various azido- and amino-deoxy sugar derivatives of glucose, galactose and xylose was synthesised via azide displacement of the corresponding triflate derivatives and subsequent modification. These compounds will be used as substrates in a high-throughput screen to identify glycosidases that can process such modified sugars. The α-glycosyl fluoride derivatives of each modified sugar were also synthesised to serve as substrates for glycosynthases derived from the enzymes identified in the screen.