Hydrogen Bonded Squaramide-Based Foldable Module Induces Both β- and α-Turns in Hairpin Structures of α-Peptides in Water

• DOI: 10.1021/acs.orglett.5b01268
• Publication Date: 2015-06-02T14:45:58Z
• Authors: Luís Martínez; Gabriel Martorell; Ángel Sampedro; Pablo Ballester; Antoni Costa; Carmen Rotger
• Keywords: Molecular Structure; Molecular Conformation; Hydrogen Bonding; Amino Acid Sequence; Peptides; Amides; 01 natural sciences; 0104 chemical sciences

A novel tertiary squaramido-based reverse-turn module SQ is reported, and its conformational properties are evaluated. This module is easily incorporated into a α-peptide sequence by conventional solid-phase peptide synthesis. The structure characterization of the hybrid squaramido-peptide 4 is described, showing that the turn segment induces the formation of hairpin structures in water through the formation of both αSQ- and βSQ-turns.