Oligomers of β-amino acid bearing non-planar amides form ordered structures

Yuko Otani, Shiroh Futaki, Tatsuto Kiwada, Yukio Sugiura, Atsuya Muranaka, Nagao Kobayashi, Masanobu Uchiyama, Kentaro Yamaguchi, Tomohiko Ohwada

Research output: Contribution to journalArticlepeer-review

27 Citations (Scopus)

Abstract

In this report, we explore the feasibility of using bicyclic chiral β-amino acids, (1R,2R,4S)- and (1S,2S,4R)-7-azabicyclo[2.2.1]heptane-2-carboxylic acid (R-Ah2c and S-Ah2c, respectively), to prepare novel peptides with unique properties. Facile cis-trans isomerization of the non-planar amide bonds of these β-amino acids should result in great flexibility of the backbone structure of β-peptides containing them. Indeed, oligomers of these amino acids showed thermostability and characteristic CD absorptions, which were not concentration-dependent, suggesting that the oligomers remained monomeric. The results indicated the formation of self-organized monomeric structures with chain-length-dependent stabilization. Energy calculations suggested that the peptides can take helical structures in which the energy barriers to cis-trans isomerization are greater for the central amide bonds than for the terminal amides.

Original languageEnglish
Pages (from-to)11635-11644
Number of pages10
JournalTetrahedron
Volume62
Issue number50
DOIs
Publication statusPublished - 2006 Dec 11

Keywords

  • Circular dichroism
  • Non-planar amide
  • Oligopeptides
  • Ordered structure
  • β-Amino acids

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Oligomers of β-amino acid bearing non-planar amides form ordered structures'. Together they form a unique fingerprint.

Cite this