A dual wavelength polymerization and bioconjugation strategy for high throughput synthesis of multivalent ligands

Zihao Li, Shashank Kosuri, Henry Foster, Jarrod Cohen, Coline Jumeaux, Molly M. Stevens, Robert Chapman, Adam J. Gormley

Research output: Contribution to journalArticle

Abstract

Structure–function relationships for multivalent polymer scaffolds are highly complex due to the wide diversity of architectures offered by such macromolecules. Evaluation of this landscape has traditionally been accomplished case-by-case due to the experimental difficulty associated with making these complex conjugates. Here, we introduce a simple dual-wavelength, two-step polymerize and click approach for making combinatorial conjugate libraries. It proceeds by incorporation of a polymerization friendly cyclopropenone-masked dibenzocyclooctyne into the side chain of linear polymers or the α-chain end of star polymers. Polymerizations are performed under visible light using an oxygen tolerant porphyrin-catalyzed photoinduced electron/energy transfer-reversible addition–fragmentation chain-transfer (PET-RAFT) process, after which the deprotection and click reaction is triggered by UV light. Using this approach, we are able to precisely control the valency and position of ligands on a polymer scaffold in a manner conducive to high throughput synthesis.

Original languageEnglish (US)
Pages (from-to)19823-19830
Number of pages8
JournalJournal of the American Chemical Society
Volume141
Issue number50
DOIs
StatePublished - Jan 1 2020

    Fingerprint

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this