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Issue 3, 2010
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Folding and self-assembling with β-oligomers based on (1R,2S)-2-aminocyclobutane-1-carboxylic acid

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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.

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

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Supplementary files

Article information


Submitted
10 Sep 2009
Accepted
19 Oct 2009
First published
03 Dec 2009

Org. Biomol. Chem., 2010,8, 564-575
Article type
Paper

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

E. Torres, E. Gorrea, K. K. Burusco, E. Da Silva, P. Nolis, F. Rúa, S. Boussert, I. Díez-Pérez, S. Dannenberg, S. Izquierdo, E. Giralt, C. Jaime, V. Branchadell and R. M. Ortuño, Org. Biomol. Chem., 2010, 8, 564
DOI: 10.1039/B918755C

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