Journal
AMINO ACIDS
Volume 41, Issue 3, Pages 663-672Publisher
SPRINGER WIEN
DOI: 10.1007/s00726-011-0887-1
Keywords
Peptidomimetics; alpha,beta-peptoids; Circular dichroism; X-ray crystallography
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Funding
- Carlsberg Foundation
- Diamond Light Source, UK
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The solution-phase synthesis and cyclisation of three alpha,beta-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 alpha,beta-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 beta-residue of the heterogeneous backbone as a key structural feature driving the increased conformational stability for octamer C.
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