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https://hdl.handle.net/2440/73045
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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 1521-3765 |
Statement of Responsibility: | 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 |
DOI: | 10.1002/chem.201200313 |
Published version: | http://dx.doi.org/10.1002/chem.201200313 |
Appears in Collections: | Aurora harvest 5 Chemistry publications |
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