Mild and efficient synthesis of ω,ω-heterodifunctionalized polymers and polymer bioconjugates

This report describes the efficient preparation of ω,ω-heterodifunctionalized polymers and polymer bioconjugates under mild conditions using a recently introduced reagent, benzotrifuranone (BTF). Demonstrated is how BTF enables introduction of differentially “clickable” functional groups ( e.g. , alkenes and alkynes) to monomethyl ether poly(ethylene glycol) amine at ambient temperature using near-stoichiometric amounts of reagents, in contrast to conventional polymer heterofunctionalization approaches that may require high temperatures, significant excesses of reagents, and/or numerous synthetic steps. Showcasing the methodology is facile access to an ω,ω-heterodifunctional polymer bearing a fluorescent (coumarin) dye and biotin. Found, in addition to avidin binding by the polymer bioconjugate, is the unexpected disruption of avidin tetramer formation.