Conformational controlviasequence for a heteropeptoid in water: coupled NMR and Rosetta modelling

Trideep Rajale, Jacob C. Miner, Ryszard Michalczyk, M. Lisa Phipps, Jurgen G. Schmidt, Robert D. Gilbertson, Robert F. Williams, Charlie E.M. Strauss, Jennifer S. Martinez

Research output: Contribution to journalArticlepeer-review


We report a critical advance in the generation and characterization of peptoid hetero-oligomers. A library of sub-monomers with amine and carboxylate side-chains are combined in different sequences using microwave-assisted synthesis. Their sequence-structure propensity is confirmed by circular dichroism, and conformer subtypes are enumerated by NMR. Biasing theψ-angle backbone totrans(180°) in Monte Carlo modelling favorsitoi+ 3 naphthyl-naphthyl stacking, and matches experimental ensemble distributions. Taken together, high-yield synthesis of heterooligomers and NMR with structure prediction enables rapid determination of sequences that induce secondary structural propensities for predictive design of hydrophilic peptidomimetic foldamers and their future libraries.

Original languageEnglish (US)
Pages (from-to)9922-9925
Number of pages4
JournalChemical Communications
Issue number77
StatePublished - Oct 4 2021

ASJC Scopus subject areas

  • Electronic, Optical and Magnetic Materials
  • General Chemistry
  • Ceramics and Composites
  • Metals and Alloys
  • Materials Chemistry
  • Surfaces, Coatings and Films
  • Catalysis


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