Synthesis and conformation of fluorinated beta-peptidic compounds

Victoria Peddie, Raymond J Butcher, Ward T Robinson, Matthew C Wilce, Daouda A K Traore, Andrew D Abell

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19 Citations (Scopus)

Abstract

Experimental and theoretical data indicate that, for alpha-fluoroamides, the FCC(O)N(H) moiety adopts an antiperiplanar conformation. In addition, a gauche conformation is favoured between the vicinal CF and CN(CO) bonds in N-beta-fluoroethylamides. This study details the synthesis of a series of fluorinated beta-peptides (1-8) designed to use these stereoelectronic effects to control the conformation of beta-peptide bonds. X-ray crystal structures of these compounds revealed the expected conformations: with fluorine beta to a nitrogen adopting a gauche conformation, and fluorine alpha to a CO group adopting an antiperiplanar conformation. Thus, the strategic placement of fluorine can control the conformation of a beta-peptide bond, with the possibility of directing the secondary structures of beta-peptides.
Original languageEnglish
Pages (from-to)6655 - 6662
Number of pages8
JournalChemistry - A European Journal
Volume18
Issue number21
DOIs
Publication statusPublished - 2012

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