The tert-butyl side chain: a powerful means to lock peptoid amide bonds in the cis conformation

Org Lett. 2013 May 3;15(9):2246-9. doi: 10.1021/ol400820y. Epub 2013 Apr 16.

Abstract

The very simple sterically hindered tert-butyl side chain exerts complete control over the peptoid amide geometry which only exists in the cis conformation. It is exemplified in NtBu glycine homo-oligomers and in linear oligopeptoids designed with an alternating cis-trans backbone amide pattern.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemistry*
  • Crystallography, X-Ray
  • Glycine / chemistry*
  • Models, Molecular
  • Molecular Conformation
  • Oligopeptides / chemistry*
  • Peptoids / chemistry*
  • Stereoisomerism

Substances

  • Amides
  • Oligopeptides
  • Peptoids
  • Glycine