Peptide-Polymer Conjugation Via Copper-Catalyzed Alkyne-Azide 1,3-Dipolar Cycloaddition

Methods Mol Biol. 2021:2355:1-7. doi: 10.1007/978-1-0716-1617-8_1.

Abstract

Dendrimers are structurally well-defined, artificial polymers with physicochemical characteristics that often imitate biomacromolecules. Consequently, they are encouraging candidates for the delivery of peptide-based vaccines. We developed a synthetic protocol for conjugating a peptide antigen derived from human papillomavirus (HPV) E7 protein to a poly(t-butyl acrylate) dendrimer to construct a vaccine candidate. The synthetic pathway utilized copper-catalyzed alkyne-azide 1,3-dipolar cycloaddition (CuAAC) click reaction, and resulted in a 76% substitution ratio of the 8-arm dendrimer. The obtained peptide-polymer construct was self-assembled, dialyzed, and characterized by microanalysis and dynamic light scattering.

Keywords: Alkyne-azide cycloaddition; Click chemistry; Peptide vaccines; Peptide-polymer conjugate.

MeSH terms

  • Alkynes
  • Azides
  • Catalysis
  • Click Chemistry
  • Copper
  • Cycloaddition Reaction*
  • Dendrimers
  • Humans
  • Peptides
  • Polymers
  • Vaccines, Subunit

Substances

  • Alkynes
  • Azides
  • Dendrimers
  • Peptides
  • Polymers
  • Vaccines, Subunit
  • Copper