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

DOI: 10.1007/s00726-011-0887-1 DOI Help

Authors: Emiliana De Santis (Medway School of Pharmacy) , Thomas Hjelmgaard (Universite Blaise Pascal) , Sophie Faure (Universite Blaise Pascal) , Olivier Roy (Universite Blaise Pascal) , Claude Didierjean (Université de Lorraine) , Bruce Alexander (University of Greenwich) , Rohanah Hussain (Diamond Light Source) , Tamas Javorfi (Diamond Light Source) , Alison Edwards (Medway School of Pharmacy) , Claude Taillefumier (Universite Blaise Pascal) , Giuliano Siligardi (Diamond Light Source)
Co-authored by industrial partner: No

Type: Journal Paper
Journal: Amino Acids , VOL 41 (3)

State: Published (Approved)
Published: April 2011

Abstract: The solution-phase synthesis and cyclisation of three ?,?-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 ?,?-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 ?-residue of the heterogeneous backbone as a key structural feature driving the increased conformational stability for octamer C.

Journal Keywords: Peptidomimetics; ?,?-Peptoids; Circular Dichroism; X-Ray Crystallography

Subject Areas: Chemistry, Biology and Bio-materials, Technique Development

Instruments: B23-Circular Dichroism