De Santis, Emiliana, Hjelmgaard, Thomas, Faure, Sophie, Roy, Olivier, Didierjean, Claude, Alexander, Bruce D., Siligardi, Giuliano, Hussain, Rohanah, Jávorfi, Tamás, Edwards, Alison A. and Taillefumier, Claude (2011) Cyclic α,β-peptoid octamers with differing side chain patterns: synthesis and conformational investigation. Amino Acids, 41 (3). pp. 663-672. ISSN 0939-4451 (Print), 1438-2199 (Online) (doi:https://doi.org/10.1007/s00726-011-0887-1)

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Abstract

The solution-phase synthesis and cyclisation of three α,β-peptoid octamers with differing side chain patterns is reported. One of these, compound C, showed a significantly greater resolution by NMR relative to the other two structurally related octamers. This observation was studied in detail by circular dichroism at a synchrotron light source to facilitate the correlation between the side chain patterns and conformational preference of these three peptoids. The X-ray crystal structure of cyclic octamer C, the first high-resolution structure for the α,β-peptoid backbone, was also obtained from methanol. Combined solid- and solution-phase studies allowed the identification of the N-2-(benzyloxy)ethyl side chain on the β-residue of the heterogeneous backbone as a key structural feature driving the increased conformational stability for octamer C

Item Type:	Article
Additional Information:	[1] First published online: 2 April 2011. [2] Published in print: August 2011.
Uncontrolled Keywords:	peptidomimetics, α,β-peptoids, circular dichroism, x-ray crystallography
Subjects:	Q Science > QD Chemistry Q Science > QP Physiology
Faculty / School / Research Centre / Research Group:	Faculty of Engineering & Science > School of Science (SCI)
Related URLs:	Publisher Organisation Organisation
Last Modified:	17 Oct 2016 09:11
URI:	http://gala.gre.ac.uk/id/eprint/7042

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