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Article Dans Une Revue Amino Acids Année : 2011

Cyclic alpha, beta-peptoid octamers with differing side chain patterns: synthesis and conformational investigation.

Résumé

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 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

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Cristallographie

Dates et versions

hal-00609665 , version 1 (19-07-2011)

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Citer

Emiliana de Santis, Thomas Hjelmgaard, Sophie Faure, Olivier Roy, Claude Didierjean, et al.. Cyclic alpha, beta-peptoid octamers with differing side chain patterns: synthesis and conformational investigation.. Amino Acids, 2011, 41, pp.663-672. ⟨10.1007/s00726-011-0887-1⟩. ⟨hal-00609665⟩
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