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Peptides with Regular Enantiomeric Sequences: A Wide Class of Modular Self-Assembling Architectures

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Abstract:

Organic trans-annular assemblies constitute an expanding class of structures with promising applications for the design of nanotechnological devices. Among the strategies developed for the engineering of organic nanotubes, those characterized by regular alternating enantiomeric amino acid sequences have been proven particularly useful. In fact, cyclic peptides with an even number of regularly alternating D- and L-amino acids have the tendency to adopt local -conformation that are capable of forming trans-annular self-assembling architectures, hydrogen bond directed. The formation of such structures is the result of the conformational equivalence of the monomer units, a general principle that associates stereo-chemical to chemical equivalence in a polymer chain. For configurationally alternating sequences the conformational equivalence produces cyclic structures, where a monomer unit is related to the adjacent along the chain by a roto-reflection axis, Sn. A slight relaxation of the conformational equivalence can formally transform a cyclic structure into a conformationally quasi-equivalent helical structures characterized by the presence of polar inner channels, which allow the transient binding for an activated flow of specific ions. To prove our early predictions, we synthesized different alternating polypeptide and the corresponding linear and cyclic oligopeptides and investigated their conformations by NMR and CD spectroscopy as well as the formation of self-assembling structures by increasing the concentration in solution. Moreover, their predicted ability to behave as an ion-channel across bilayer membranes are investigated and experimental evidence of single molecule conducting events are reported. Finally, the possibility is suggested to obtain self-assembled trans-annular structures by chemically bridging the amino acid side chains stabilized using different strategies. A complex construct with good perspective for nano-technological applications is proposed in which cyclic DL-lysine side chains are bridged by the formation of salycilaldimmine metal chelates.

Keywords: SELF-ASSEMBLING ARCHITECTURES; TRANS-ANNULAR ASSEMBLIES; TRANS-ANNULAR STRUCTURES

Document Type: Research Article

DOI: http://dx.doi.org/10.1166/jnn.2007.644

Publication date: July 1, 2007

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  • Journal for Nanoscience and Nanotechnology (JNN) is an international and multidisciplinary peer-reviewed journal with a wide-ranging coverage, consolidating research activities in all areas of nanoscience and nanotechnology into a single and unique reference source. JNN is the first cross-disciplinary journal to publish original full research articles, rapid communications of important new scientific and technological findings, timely state-of-the-art reviews with author's photo and short biography, and current research news encompassing the fundamental and applied research in all disciplines of science, engineering and medicine.
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