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Type: Journal article
Title: Synthesis and conformation of fluorinated β-peptidic compounds
Other Titles: Synthesis and conformation of fluorinated beta-peptidic compounds
Author: Peddie, V.
Butcher, R.
Robinson, W.
Wilce, M.
Traore, D.
Abell, A.
Citation: Chemistry-A European Journal, 2012; 18(21):6655-6662
Publisher: Wiley-V C H Verlag GMBH
Issue Date: 2012
ISSN: 0947-6539
Statement of
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
RMID: 0020119131
DOI: 10.1002/chem.201200313
Appears in Collections:Chemistry publications

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