Abstract
The cellular glycocalyx and extracellular matrix are rich in glycoproteins and proteoglycans that play essential physical and biochemical roles in all life. Synthetic mimics of these natural bottlebrush polymers have wide applications in biomedicine, yet preparation has been challenged by their high grafting and glycosylation densities. Using one-pot dual-catalysis polymerization of glycan-bearing α-amino acid N-carboxyanhydrides, we report grafting-from glycopolypeptide brushes. The materials are chemically and conformationally tunable where backbone and sidechain lengths were precisely altered, grafting density modulated up to 100%, and glycan density and identity tuned by monomer feed ratios. The glycobrushes are composed entirely of sugars and amino acids, are non-toxic to cells, and are degradable by natural proteases. Inspired by native lipid-anchored proteoglycans, cholesterol-modified glycobrushes were displayed on the surface of live human cells. Our materials overcome long-standing challenges in glycobrush polymer synthesis and offer new opportunities to examine glycan presentation and multivalency from chemically defined scaffolds.
Highlights
The cellular glycocalyx and extracellular matrix are rich in glycoproteins and proteoglycans that play essential physical and biochemical roles in all life
The extracellular matrix (ECM) is another region rich in a glycoprotein subclass termed proteoglycans[2]. Both glycoproteins and proteoglycans are composed of a polypeptide backbone with enzymatically grafted saccharide chains originating predominantly at serine (Ser), threonine, and asparagine residues
Biosynthesis of proteoglycans and glycoproteins is controlled by 1000+ enzymes and yields a heterogeneous and complex mixture of structures[2]
Summary
The cellular glycocalyx and extracellular matrix are rich in glycoproteins and proteoglycans that play essential physical and biochemical roles in all life. The method is precisely tunable within the same parameters as natural glycobrushes including polypeptide backbone composition and chain length, glyco-sidechain length and graft density, glycan identity, and chain conformation.
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