Chemoselective, Postpolymerization Modification of Bioactive, Degradable Polymers.

Biomacromolecules

Department of Chemistry , Massachusetts Institute of Technology, Cambridge , Massachusetts 02139 , United States.

Published: February 2019

Degradable polymers promote sustainability, mitigate environmental impact, and facilitate biological applications. Tailoring degradable polymers is challenging because installing functional group-rich side chains is difficult when the backbone itself is susceptible to degradation. A convenient means of side chain installation is through postpolymerization modification (PPM). In functionalizing polyoxazinones, a class of degradable polymers generated by the ring-opening metathesis polymerization (ROMP), we predictably found PPM challenging. Even the versatile azide-alkyne cycloaddition click reaction was ineffective. To solve this problem, we screened PPM reactions whose efficiencies could be assessed using photochemistry (excimer formation). The mildest, pH-neutral process was functionalization of a ketone-containing polymer to yield either oxime (acid labile)- or alkyoxylamine (stable)-substituted polymers. Using this approach, we equipped polymers with fluorophores, reporter groups, and bioactive epitopes. These modifications imbued the polymers with distinctive spectral properties and biological activities. Thus, polyoxazinones are now tunable through a modular method to diversify these macromolecules' function.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6690479PMC
http://dx.doi.org/10.1021/acs.biomac.8b01631DOI Listing

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