Diastereotopic fluorine substituents as 19F NMR probes of screw-sense preference in helical foldamers

Org Biomol Chem. 2013 May 21;11(19):3168-76. doi: 10.1039/c3ob40463c. Epub 2013 Apr 5.

Abstract

Ligating simple amino alcohol or amino ester monomers containing enantiotopic fluorine substituents to the C-terminus of a helical peptide places the fluorine atoms in diastereotopic environments, and gives two distinct and easily identifiable signals in the (19)F NMR spectrum. In the case of a dynamically inverting helix built from achiral monomers, the chemical shift separation between the (19)F signals provides a simple means of analysing the ratio of screw-sense conformers in the oligomer, in cases where an asymmetric bias leads to a screw-sense preference.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Crystallography, X-Ray
  • Fluorescent Dyes / chemical synthesis
  • Fluorescent Dyes / chemistry*
  • Fluorine / chemistry*
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Structure
  • Peptides / chemistry*
  • Protein Folding
  • Stereoisomerism

Substances

  • Fluorescent Dyes
  • Peptides
  • Fluorine