Fluorescent Labelling of Glycans with FRET-Based Probes in a Gold(III)-Mediated Three-Component Coupling Reaction.

Abstract

Single-site multifunctionalization of glycans is of importance in biological studies considering its crucial role in mediating biological events and human diseases. In this paper, a novel approach for multifunctional labelling of glycans has been developed featuring the use of fluorescence resonance energy transfer-based (FRET-based) probes for fluorescent labelling of glycans through a gold(III)-mediated three-component coupling reaction. Oxidation of glycans into aldehydes followed by the A3 -coupling reaction with FRET-based probes resulted in the single-site formation of fluorescent propargylamine products. The conversion of labelled glycans can be revealed by ratiometric analysis of the FRET signals. This labelling approach results in multifunctionalization of glycans with high selectivity and conversion between 66 and 69 %.