Anthranilic Acid as a Versatile Fluorescent Tag and Linker for Functional Glycomics

The advancement of glycoscience is critically dependent on the access to a large number of glycans for their functional study. Naturally occurring glycans are considered a viable source for diverse and biologically relevant glycan libraries. A mixture of free reducing glycans released from natural sources can be fluorescently tagged and separated by chromatography to produce a natural glycan library. Anthranilic acid (AA) has been widely used to fluorescently tag reducing glycans for HPLC or LC/MS analysis. However, AA conjugated glycans are not efficiently immobilized on microarray slides due to the lack of a primary alkylamine functional group. In this study, we have developed simple and efficient chemistry for bioconjugation and further functionalization of glycan–AA conjugates. This new approach enables quick preparation of glycan microarrays and neoglycoproteins from glycan–AA conjugates, which can be separated by weak anion exchange (WAX) and C18 reversed-phase HPLC.