Building a successful structural motif into sialylmimetics—cyclohexenephosphonate monoesters as pseudo-sialosides with promising inhibitory properties

A variable synthesis of a new class of sialylmimetics which provides access to pseudo-sialosides containing the successful cyclohexene motif in the sialic acid mimicking part has been developed. The d- and l-xylo cyclohexenephosphonate scaffolds allow attachment of selected aglycons or aglycon mimetics via mixed phosphonate diester strategies and some target compounds thus synthesized displayed promising inhibitory properties when tested with parasitic or bacterial sialidases.

A systematic synthetic approach to sialylmimetics containing a cyclohexenephosphonate scaffold has been developed which allows their incorporation into pseudo-disaccharidic systems. Thus, mimicking of the full structural space displayed by natural sialosides as substrates, products or as intermediates in enzymatic reactions is possible and inhibitory activity toward selected sialidases is obtained.Figure optionsDownload as PowerPoint slide