Abstract
Sialic acids are located at the termini of mammalian cell-surface glycostructures, which participate in essential interaction processes including adhesion of pathogens prior to infection and immunogenicity. Here we present the synthesis and bioorthogonal metabolic incorporation of the sialic acid analogue N-(1-oxohex-5-ynyl)neuraminic acid (Neu5Hex) into the cell-surface glycocalyx of a human larynx carcinoma cell line (HEp-2) and its fluorescence labelling by click chemistry.
Highlights
The surface of eukaryotic cells is heavily covered with glycan structures of various types forming the individual, dynamic glycocalyx of each cell type
Neu5Hex (3) is a new substrate for metabolic glycoengineering which is proposed to be incorporated into the cell surface glycan structures
Sialic acids are prominent sugars which are located in the terminal position on cell-surface glycans
Summary
The surface of eukaryotic cells is heavily covered with glycan structures of various types forming the individual, dynamic glycocalyx of each cell type. We present the synthesis and bioorthogonal metabolic incorporation of the sialic acid analogue N-(1-oxohex-5-ynyl)neuraminic acid (Neu5Hex) into the cell-surface glycocalyx of a human larynx carcinoma cell line (HEp-2) and its fluorescence labelling by click chemistry. The efficient uptake and incorporation of sialic acid modified in positions C-5 and C-9 into human B-lymphoma cells (BJA-B), Jurkat and others including primary cells has been demonstrated [3,7].
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