Solid-phase synthesis and circular dichroism study of β-abpeptoids

Ganesh A. Sable, Kang Ju Lee, Hyun-Suk Lim

Research output: Contribution to journalArticle

Abstract

The development of peptidomimetic foldamers that can form well-defined folded structures is highly desirable yet challenging. We previously reported on α-ABpeptoids, oligomers of N-alkylated β2-homoalanines and found that due to the presence of chiral methyl groups at α-positions, α-ABpeptoids were shown to adopt folding conformations. Here, we report β-ABpeptoids having chiral methyl group at β-positions rather than α-positions as a different class of peptoids with backbone chirality. We developed a facile solid-phase synthetic route that enables the synthesis of β-ABpeptoid oligomers ranging from 2-mer to 8-mer in excellent yields. These oligomers were shown to adopt ordered folding conformations based on circular dichroism (CD) and NMR studies. Overall, these results suggest that β-ABpeptoids represent a novel class of peptidomimetic foldamers that will find a wide range of applications in biomedical and material sciences.

Original languageEnglish (US)
Article number178
JournalMolecules
Volume24
Issue number1
DOIs
StatePublished - Jan 5 2019

Fingerprint

Peptidomimetics
Solid-Phase Synthesis Techniques
Circular Dichroism
oligomers
Oligomers
dichroism
solid phases
Peptoids
folding
Conformations
synthesis
Chirality
Materials science
materials science
chirality
routes
Nuclear magnetic resonance
nuclear magnetic resonance
alpha-aminobutyric acid

Keywords

  • Foldamers
  • Peptidomimetics
  • Peptoids
  • Solid-phase synthesis
  • β-ABpeptoids

ASJC Scopus subject areas

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Solid-phase synthesis and circular dichroism study of β-abpeptoids. / Sable, Ganesh A.; Lee, Kang Ju; Lim, Hyun-Suk.

In: Molecules, Vol. 24, No. 1, 178, 05.01.2019.

Research output: Contribution to journalArticle

Sable, Ganesh A. ; Lee, Kang Ju ; Lim, Hyun-Suk. / Solid-phase synthesis and circular dichroism study of β-abpeptoids. In: Molecules. 2019 ; Vol. 24, No. 1.
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