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Cyclic a,ß-peptoid octamers with differing side chain patterns: synthesis and conformational investigation

De Santis, Emiliana, Hjelmgaard, Thomas, Faure, Sophie, Roy, Oliver, Didierjean, Claude, Alexander, Bruce D., Siligardi, Giuliano, Hussain, Rohanah, Javorfi, Tamas, Edwards, Alison A., and others. (2011) Cyclic a,ß-peptoid octamers with differing side chain patterns: synthesis and conformational investigation. Amino Acids, 41 (3). pp. 663-672. ISSN 1438-2199. (doi:10.1007/s00726-011-0887-1) (The full text of this publication is not currently available from this repository. You may be able to access a copy if URLs are provided)

The full text of this publication is not currently available from this repository. You may be able to access a copy if URLs are provided. (Contact us about this Publication)
Official URL
http://dx.doi.org/10.1007/s00726-011-0887-1

Abstract

The solution-phase synthesis and cyclisation of three ?,?-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 ?,?-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 ?-residue of the heterogeneous backbone as a key structural feature driving the increased conformational stability for octamer C.

Item Type: Article
DOI/Identification number: 10.1007/s00726-011-0887-1
Additional information: number of additional authors: 10;
Uncontrolled keywords: Peptidomimetics, ?,?-peptoids, Circular dichroism, X-ray crystallography
Subjects: Q Science
R Medicine > RS Pharmacy and materia medica
Divisions: Faculties > Sciences > Medway School of Pharmacy
Depositing User: Stewart Brownrigg
Date Deposited: 07 Mar 2014 00:05 UTC
Last Modified: 29 May 2019 12:24 UTC
Resource URI: https://kar.kent.ac.uk/id/eprint/40412 (The current URI for this page, for reference purposes)
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