Stereospecific synthesis of conformationally constrained γ-amino acids: New foldamer building blocks that support helical secondary structure

Li Guo, Yonggui Chi, Aaron M. Almeida, Ilia A. Guzei, Brian K. Parker, Samuel H. Gellman

Research output: Contribution to journalArticlepeer-review

122 Scopus citations

Abstract

(Figure Presented) A highly stereoselective synthesis of novel cyclically constrained γ-amino acid residues is presented. The key step involves organocatalytic Michael addition of an aldehyde to 1-nitrocyclohexene. After aldehyde reduction, this approach provides optically active β-substituted δ-nitro alcohols (96-99% ee), which can be converted to γ-amino acid residues with a variety of substituents at the α position. We have used these new building blocks to prepare α/γ-peptide foldamers that adopt a specific helical conformation in solution and in the solid state.

Original languageEnglish (US)
Pages (from-to)16017-16020
Number of pages4
JournalJournal of the American Chemical Society
Volume131
Issue number44
DOIs
StatePublished - 2009
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry
  • Biochemistry
  • Colloid and Surface Chemistry

Fingerprint

Dive into the research topics of 'Stereospecific synthesis of conformationally constrained γ-amino acids: New foldamer building blocks that support helical secondary structure'. Together they form a unique fingerprint.

Cite this