title: Synthesis and conformation of fluorinated β-peptidic compounds.
abstract: Experimental and theoretical data indicate that, for α-fluoroamides, the F-C-C(O)-N(H) moiety adopts an antiperiplanar conformation. In addition, a gauche conformation is favoured between the vicinal C-F and C-N(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 C=O 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.
authors.affiliation: School of Chemistry and Physics, The University of Adelaide, Adelaide, SA 5005, Australia.
authors.forename: Victoria
authors.initials: V
authors.lastname: Peddie
authors.forename: Raymond J
authors.initials: RJ
authors.lastname: Butcher
authors.forename: Ward T
authors.initials: WT
authors.lastname: Robinson
authors.forename: Matthew C J
authors.initials: MC
authors.lastname: Wilce
authors.forename: Daouda A K
authors.initials: DA
authors.lastname: Traore
authors.forename: Andrew D
authors.initials: AD
authors.lastname: Abell
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D018360:Crystallography, X-Ray; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry*; D007202:Indicators and Reagents; D008958:Models, Molecular; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry*; D017433:Protein Structure, Secondary
chemical_list: D000596:Amino Acids; D006845:Hydrocarbons, Fluorinated; D007202:Indicators and Reagents; D010455:Peptides