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|Title:||Synthesis and conformation of fluorinated β-peptidic compounds|
|Other Titles:||Synthesis and conformation of fluorinated beta-peptidic compounds|
|Citation:||Chemistry-A European Journal, 2012; 18(21):6655-6662|
|Publisher:||Wiley-V C H Verlag GMBH|
|Victoria Peddie, Raymond J. Butcher, Ward T. Robinson, Matthew C. J. Wilce, Daouda A. K. Traore, and Andrew D. Abell|
|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.|
|Keywords:||Amino acids; conformation analysis; organofluorine; peptides; X-ray diffraction|
|Rights:||Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim|
|Appears in Collections:||Chemistry publications|
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