α-Functional glycopolymers: New materials for (poly)peptide conjugation

The synthesis and characterization of a number of N-(hydroxy)succinimidyl ester-terminated glycopolymers obtained via copper(I)-catalysed living radical polymerisation have been described. Monomers employed were based on protected glucose and galactose, glucofuranoside monomer (1) and galactopyranoside monomer (2). The corresponding polymers featured a relatively narrow molecular weight distribution (PDI=1.10–1.31) and Mn between 4.5 and 10.2 kDa. The protecting groups were removed by treatment with formic acid. Analogous fluorescent polymers have been synthesized by copolymerisation of a monomer which fluoresces in the visible, the fluorescent behaviour of these materials has been investigated. Preliminary experiments have also shown that the terminally functional sugar polymers can react with molecules containing primary amino groups and some triblock ABA copolymers have been prepared.