Synthesis and Conformation of Fluorinated β‐Peptidic Compounds |
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| Authors: | Dr Victoria Peddie Prof Raymond J Butcher Prof Ward T Robinson Prof Matthew C J Wilce Dr Daouda A K Traore Prof Andrew D Abell |
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| Affiliation: | 1. School of Chemistry and Physics, The University of Adelaide, Adelaide, SA 5005 (Australia), Fax: (+61)?8‐8303‐4380;2. Department of Chemistry, University of Canterbury, Private Bag 4800, Christchurch (New Zealand);3. Department of Chemistry, Howard University, Washington DC 20059 (USA);4. Department of Biochemistry and Molecular Biology, Monash University, Clayton, Victoria 3168 (Australia) |
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| 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. |
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| Keywords: | amino acids conformation analysis organofluorine peptides X‐ray diffraction |
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