Dynamic glycosylation of liposomes by thioester exchange

The interplay of dynamic functionalization and specific molecular recognition on biological membranes is key to numerous physiological processes. In this work we present a simple glycocalyx model based on the covalent yet reversible glycosylation of liposomes and subsequent recognition by a lectin. Reversible thioester exchange of membrane embedded amphiphilic thioesters with thiol-tagged D-mannose in solution is performed at physiologically relevant conditions. Recognition with the lectin concanavalin A is possible directly from this reaction mixture, leading to liposome agglutination. To the best of our knowledge, the dynamic covalent glycosylation of liposomes is so far unprecedented.