Facile protocol for the synthesis of self-assembling polyamine-based peptide amphiphiles (PPAs) and related biomaterials

Mehdi Bin Samad, Krishnaiah Maddeboina, Nathalia Rodrigues de Almeida, Martin Conda-Sheridan

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

Polyamine-based Peptide Amphiphiles (PPAs) are a new class of self-assembling amphiphilic biomaterials-related to the peptide amphiphiles (PAs). Traditional PAs possess charged amino acids as solubilizing groups (lysine, arginine), which are directly connected to a lipid segment or can contain a linker region made of neutral amino acids. Tuning the peptide sequence of PAs can yield diverse morphologies. Similarly, PPAs possess a hydrophobic segment and neutral amino acids, but also contain polyamine molecules as water solubilizing (hydrophilic) groups. As is the case with PAs, PPAs can also self-assemble into diverse morphologies, including small rods, twisted nano-ribbons, and fused nano-sheets, when dissolved in water. However, the presence of both primary and secondary amines on a single polyamine molecule poses a significant challenge when synthesizing PPAs. In this paper, we show a simple protocol, based on literature precedents, to achieve a facile synthesis of PPAs using solid phase peptide synthesis (SPPS). This protocol can be extended to the synthesis of PAs and other similar systems. We also illustrate the steps that are needed for cleavage from the resin, identification, and purification.

Original languageEnglish (US)
Article numbere57908
JournalJournal of Visualized Experiments
Volume2018
Issue number136
DOIs
StatePublished - Jun 25 2018

Keywords

  • Biomaterials
  • Chemistry
  • Issue 136
  • Nanofiber
  • Nanoparticle
  • Orthogonal protecting groups
  • Peptide amphiphiles
  • Peptide synthesis
  • Polyamine peptide amphiphiles
  • Self-assembly

ASJC Scopus subject areas

  • Neuroscience(all)
  • Chemical Engineering(all)
  • Biochemistry, Genetics and Molecular Biology(all)
  • Immunology and Microbiology(all)

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