Chemoselective reaction of methoxyaminomethyl BODIPYs with unprotected carbohydrates: a powerful tool for accessing BODIPY neoglycosides

Abstract

The neoglycosylation of methoxyaminomethyl-appended BODIPYs with unprotected reducing mono-, di-, and trisaccharides produces, in a regio- and stereoselective manner, cyclic N-glycosyl-N-methoxy–BODIPY conjugates, as a relevant class of neoglycosides that display excellent photophysical characteristics in pure water, even at high dye concentrations. In addition, the cellular uptake of some of the neoglycosylated BODIPYs has been confirmed via fluorescence microscopy, and a BODIPY–acarbose conjugate showed comparable enzymatic inhibitory activity to acarbose for two different α-amylases: A. oryzae α-amylase (AOA) and human salivary α-amylase (HSA).