Premium
Synthesis and Conformation of Fluorinated β‐Peptidic Compounds
Author(s) -
Peddie Victoria,
Butcher Raymond J.,
Robinson Ward T.,
Wilce Matthew C. J.,
Traore Daouda A. K.,
Abell Andrew D.
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201200313
Subject(s) - alkane stereochemistry , moiety , chemistry , vicinal , fluorine , peptide , stereochemistry , peptide bond , peptide conformation , crystal structure , crystallography , organic chemistry , biochemistry
Experimental and theoretical data indicate that, for α‐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 ‐β‐fluoroethylamides. This study details the synthesis of a series of fluorinated β‐peptides ( 1 – 8 ) designed to use these stereoelectronic effects to control the conformation of β‐peptide bonds. X‐ray crystal structures of these compounds revealed the expected conformations: with fluorine β to a nitrogen adopting a gauche conformation, and fluorine α to a CO group adopting an antiperiplanar conformation. Thus, the strategic placement of fluorine can control the conformation of a β‐peptide bond, with the possibility of directing the secondary structures of β‐peptides.