Structural Tuning and Conformational Stability of Aromatic Oligoamide Foldamers

Riia Annala; Aku Suhonen; Heikki Laakkonen; Perttu Permi; Maija Nissinen

doi:10.1002/chem.201703985

Structural Tuning and Conformational Stability of Aromatic Oligoamide Foldamers

Chemistry. 2017 Nov 21;23(65):16671-16680. doi: 10.1002/chem.201703985. Epub 2017 Nov 3.

Authors

Riia Annala¹, Aku Suhonen¹, Heikki Laakkonen¹, Perttu Permi^{1

2}, Maija Nissinen¹

Affiliations

¹ Department of Chemistry, Nanoscience Center, University of Jyvaskyla, P.O. Box 35, 40014 University of, Jyvaskyla, Finland.
² Department of Chemistry and Department of Biological and Environmental Sciences, Nanoscience Center, University of Jyvaskyla, P.O. Box 35, 40014 University of, Jyvaskyla, Finland.

PMID: 29105164
DOI: 10.1002/chem.201703985

Abstract

A series of aromatic oligoamide foldamers with two or three pyridine-2,6-dicarboxamide units as their main folding motifs and varying aromatic building blocks as linkers have been synthetized to study the effects of the structural variation on the folding properties and conformational stability. Crystallographic studies showed that in the solid state the central linker unit either elongates the helices and more open S-shaped conformations, compresses the helices to more compact conformations, or acts as a rigid spacer separating the pyridine-2,6-dicarboxamide units, which for their part add the predictability of the conformational properties. Multidimensional NMR studies showed that, even in solution, foldamers show conformational stability and folded conformations comparable to the solid-state structures.

Keywords: NMR spectroscopy; X-ray crystallography; foldamers; hydrogen bonding; molecular folding.