Abstract
Glycosyl monomers for the assembly of multivalent ligands are typically synthesized using carbohydrates with biological functions and polymerizable functional groups such as acrylamide or styrene introduced into the carbohydrate aglycon, and monomers polymerized using a radical initiator. Herein, we report the acryloylation of 6-aminohexyl α-d-mannoside and its conversion into the glycosyl monomer bearing an acrylamide group. The general acryloylation procedure afforded the desired N-hexyl α-d-acetylmannosyl acrylamide monomer as well as an unexpected compound with a close Rf value. The compounds were separated and analyzed by nuclear magnetic resonance spectroscopy and mass spectrometry, which revealed the unknown compound to be the bivalent N,N-bis(hexyl α-d-acetylmannosyl) acrylamide monomer, which contains two hexyl mannose units and one acrylamide group. To the best of our knowledge, this side reaction has not previously been disclosed, and may be useful for the construction of multivalent sugar ligands.
Highlights
Many biological events in organisms are associated with carbohydrates on cell surfaces [1,2,3,4]
Multivalency, which is important for carbohydrate–protein interactions, has been imitated by synthetic polymers that contain carbohydrates; this affinity-enhancing effect of a multivalent ligand is known as the “cluster effect”
Studies into the preparation of glycomonomers and glycopolymers has continued to date with the aim of clarifying the biological mechanism and applying them to devices and biomaterials [14,15,16,17]
Summary
Many biological events in organisms are associated with carbohydrates on cell surfaces [1,2,3,4]. The clusters, as multivalent ligands, interact with CBMs to induce biological events [5,6,7]. A previously undocumented side-reaction was observed during acryloylation, the product of which was separated by silica-gel column chromatography and identified by nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry (MS) to be N,N-bis(hexyl α-D-acetylmannosyl) acrylamide, which is a bivalent monomer containing two mannose residues. The discovery of this unusual bivalent monomer is described
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