Conformational rearrangements by water-soluble peptoid foldamers

Sung Bin Y. Shin, Kent Kirshenbaum

Research output: Contribution to journalArticlepeer-review

Abstract

Peptoids are a family of N-substituted glycine oligomers that are capable of forming stable helical structures. We seek peptoid monomers that can establish a strong folding propensity in aqueous conditions. Here we utilize L-phenylalanine tert-butyl ester as a readily available reagent for the synthesis of (S)-N-(1-carboxy-2-phenylethyl)glycine oligomers. The products form stable secondary structures in aqueous solution in which the conformation is dramatically responsive to variations in pH and solvent composition.

Original languageEnglish (US)
Pages (from-to)5003-5006
Number of pages4
JournalOrganic Letters
Volume9
Issue number24
DOIs
StatePublished - Nov 22 2007

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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