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

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Organic & Biomolecular Chemistry Vol -7

Organic & Biomolecular Chemistry Vol -6

Organic & Biomolecular Chemistry Vol -5

Organic & Biomolecular Chemistry Vol -4

Organic & Biomolecular Chemistry Vol -3

Organic & Biomolecular Chemistry Vol -2

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

Content Provider	Royal Society of Chemistry (RSC)
Author	Ortuño, Rosa M. Giralt, Ernest Jaime, Carlos Dannenberg, Samantha Nolis, Pau Rúa, Federico Izquierdo, Sandra Silva, Eric Da Burusco, Kepa K. Boussert, Stéphanie Branchadell, Vicenç Gorrea, Esther Torres, Elisabeth Díez-Pérez, Ismael
Copyright Year	2010
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.
Starting Page	564
Ending Page	575
Page Count	12
File Format	HTM / HTML PDF
ISSN	14770520
Volume Number	8
Issue Number	3
Journal	Organic & Biomolecular Chemistry
DOI	10.1039/b918755c
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Octane SPFM Transmission electron microscopy Molecular modelling Carboxylic acid Conformational isomerism Hydrophobe
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Biochemistry Physical and Theoretical Chemistry

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Designing hybrid foldamers: the effect on the peptide conformational bias of β- versus α- and γ-linear residues in alternation with (1R,2S)-2-aminocyclobutane-1-carboxylic acid.

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