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- Title
Cyclic α,β-peptoid octamers with differing side chain patterns: synthesis and conformational investigation.
- Authors
Santis, Emiliana; Hjelmgaard, Thomas; Faure, Sophie; Roy, Olivier; Didierjean, Claude; Alexander, Bruce; Siligardi, Giuliano; Hussain, Rohanah; Jávorfi, Tamás; Edwards, Alison; Taillefumier, Claude
- 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.
- Subjects
GLYCINE; PEPTIDE synthesis; CONFORMATIONAL analysis; RING formation (Chemistry); SYNCHROTRONS; CIRCULAR dichroism; X-ray crystallography; STATISTICAL correlation; MOLECULAR structure
- Publication
Amino Acids, 2011, Vol 41, Issue 3, p663
- ISSN
0939-4451
- Publication type
Article
- DOI
10.1007/s00726-011-0887-1