C6-Substituted methanopyrrolidine β-amino acid: synthesis and characterization of oligomeric foldamers

Zilun Hu, Guoliang Lin, Matthew Sender, Kevin C. Cannon, Franklin A. Davis, Grant R. Krow

Research output: Contribution to journalArticle

Abstract

Highly conformation constrained β-proline based methanopyrrolidine-5-carboxylic acids (6, MetPyr-5-acids, or MetPyr-β-amino acids) derivatives were designed, synthesized, and investigated to control peptide conformation and oligomer folding. Enhanced order of folding uniformity correlated with length of the prepared homo-oligomers as characterized by circular dichroism (CD). The octamer (34) exhibited minimal solvent effects and was stable with increasing temperature up to 80 °C. Substitutions on C6 of the 2-azabicyclo[2.1.1] hexane structure could modulate the amide cis/trans conformation.

Original languageEnglish (US)
Article number152240
JournalTetrahedron Letters
Volume61
Issue number35
DOIs
StatePublished - Aug 27 2020

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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