title: Cyclic α,β-peptoid octamers with differing side chain patterns: synthesis and conformational investigation.
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.
authors: Medway School of Pharmacy, Universities of Kent and Greenwich at Medway, Central Avenue, Chatham Maritime, Kent, UK.
authors: Emiliana
authors: E
authors: De Santis
authors: Thomas
authors: T
authors: Hjelmgaard
authors: Sophie
authors: S
authors: Faure
authors: Olivier
authors: O
authors: Roy
authors: Claude
authors: C
authors: Didierjean
authors: Bruce D
authors: BD
authors: Alexander
authors: Giuliano
authors: G
authors: Siligardi
authors: Rohanah
authors: R
authors: Hussain
authors: Tamás
authors: T
authors: Jávorfi
authors: Alison A
authors: AA
authors: Edwards
authors: Claude
authors: C
authors: Taillefumier
mesh_terms: D002942:Circular Dichroism; D018360:Crystallography, X-Ray; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D034444:Peptoids / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D034444:Peptoids