Folding and self-assembling with β-oligomers based on (1R,2S)-2-aminocyclobutane-1-carboxylic acid

Elisabeth Torres, Esther Gorrea, Kepa K. Burusco, Eric Da Silva, Pau Nolis, Federico Rúa, Stéphanie Boussert, Ismael Díez-Pérez, Samantha Dannenberg, Sandra Izquierdo, Ernest Giralt, Carlos Jaime, Vicen Branchadell, Rosa M. Ortuño

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49 Citations (Scopus)

Abstract

Improved methodologies are provided to synthesize (1R,2S)-2- aminocyclobutane-1-carboxylic acid derivatives and their incorporation into β-peptides of 2-8 residues bearing different N-protecting groups. The conformational analysis of these oligomers has been carried out by using experimental techniques along with theoretical calculations. This study shows that these oligomers adopt preferentially a strand-type conformation in solution induced by the formation of intra-residue six-membered hydrogen-bonded rings, affording cis-fused [4.2.0]octane structural units that confer high rigidity on these β-peptides. Moreover, all of them are prone to self-assemble producing nano-sized fibres, as evidenced by TEM, AFM and SPFM, and, in some instances, they also form gels. These techniques and molecular modelling allowed us to suggest an aggregation model for the assembly structures in which a parallel molecular-arrangement is preferred and the conformation is similar to that observed in solution. According to this model, both hydrogen-bonding and hydrophobic interactions would account for formation of the assemblies. © 2010 The Royal Society of Chemistry.
Original languageEnglish
Pages (from-to)564-575
JournalOrganic and Biomolecular Chemistry
Volume8
Issue number3
DOIs
Publication statusPublished - 1 Jan 2010

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