Turning Peptide Sequences into Ribbon Foldamers by a Straightforward Multicyclization Reaction. (23rd September 2015)

• Record Type: Journal Article
• Authors: Martin, Vincent; Legrand, Baptiste; Vezenkov, Lubomir L.; Berthet, Mathéo; Subra, Gilles; Calmès, Monique; Bantignies, Jean‐Louis; Martinez, Jean; Amblard, Muriel
• Is Part Of: Angewandte Chemie. Volume 127:Number 47(2015)
• Page Start: 14172
• Page End: 14176
• Publication Date: 2015-09-23
• Subjects: α‐Amino‐γ‐lactame -- Bandartige Strukturen -- Festphasensynthesen -- Foldamere -- Multicyclisierungen; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201506955
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: The conformational control of molecular scaffolds allows the display of functional groups in defined spatial arrangement. This is of considerable interest for developing fundamental and applied systems in both the fields of biology and material sciences. Peptides afford a large diversity of functional groups, and peptide synthetic routes are very attractive and accessible. However, most short peptides do not possess well‐defined secondary structures. Herein, we developed a simple strategy for converting peptide sequences into structured γ‐lactam‐containing oligomers while keeping the amino acids side chain diversity. We showed the propensity of these molecules to adopt ribbon‐like secondary structures. The periodic distribution of the functional groups on both sides of the ribbon plane is encoded by the initial peptide sequence. Abstract : Bandgymnastik : Eine direkte Festphasenmethode zur Umwandlung herkömmlicher Proteinsequenzen in γ‐Lactam‐haltige Oligomere mit bandartiger Struktur wird vorgestellt. Die kontrollierte periodische Verteilung funktioneller Gruppen auf beiden Seiten des Bandes wird einfach in der Peptidsequenz kodiert, sodass vielseitige Substanzen für biomedizinische Anwendungen und Materialwissenschaften zugänglich sind.