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

Sarah J. Pike, Matteo De Poli, Wojciech Zawodny, James Raftery, Simon J. Webb, Jonathan Clayden*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)

25 Citations (Scopus)

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 19F NMR spectrum. In the case of a dynamically inverting helix built from achiral monomers, the chemical shift separation between the 19F 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.

Original languageEnglish
Pages (from-to)3168-3176
Number of pages9
JournalOrganic and Biomolecular Chemistry
Volume11
Issue number19
Early online date27 Mar 2013
DOIs
Publication statusPublished - 21 May 2013

Fingerprint Dive into the research topics of 'Diastereotopic fluorine substituents as 19F NMR probes of screw-sense preference in helical foldamers'. Together they form a unique fingerprint.

  • Cite this