Cyclic α,β-peptoid octamers with differing side chain patterns: synthesis and conformational investigation

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)

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

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