Issue 10, 2006

Parallel assembly of dipolar columns composed of a stacked cyclic tri-β-peptide

Abstract

A novel cyclic trimer of a β-amino acid, trans-2-aminocyclohexylcarboxylic acid, was synthesized and its conformation and ability to form assemblies investigated. FT-IR and NMR measurements and computational calculations showed that this cyclic tri-β-peptide has a C3-symmetric conformation with trans amide groups. A notable feature of the conformation is a vertical and parallel orientation of the three amide groups to the cyclic skeleton. The cyclic tri-β-peptide was crystallized from a solution in trifluoroacetic acidmethanol (or trifluoroacetic acidwater) to yield a rod-shaped molecular assembly, as observed by TEM. The electron crystallography of the rod-shaped assembly both in suspension and in ultrathin cross-section revealed that the cyclic tri-β-peptides were stacked up to form molecular columns, and that a two-fold screw symmetry operation along the column direction was present in the unit cell, which contained two cyclic tri-β-peptides. This indicates that all the amide groups are oriented in the same direction. Since any two molecular columns are staggered by a quarter of a c-axis length and aligned parallel to each other, the dipole moments of the columns are aligned to enhance the strength additively in the whole assembly.

Graphical abstract: Parallel assembly of dipolar columns composed of a stacked cyclic tri-β-peptide

Article information

Article type
Paper
Submitted
11 Jan 2006
Accepted
16 Mar 2006
First published
13 Apr 2006

Org. Biomol. Chem., 2006,4, 1896-1901

Parallel assembly of dipolar columns composed of a stacked cyclic tri-β-peptide

F. Fujimura, M. Fukuda, J. Sugiyama, T. Morita and S. Kimura, Org. Biomol. Chem., 2006, 4, 1896 DOI: 10.1039/B600407E

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements