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Structural Tuning and Conformational Stability of Aromatic Oligoamide Foldamers
Author(s) -
Annala Riia,
Suhonen Aku,
Laakkonen Heikki,
Permi Perttu,
Nissinen Maija
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201703985
Subject(s) - chemistry , folding (dsp implementation) , linker , crystallography , foldamer , solid state , pyridine , stereochemistry , organic chemistry , computer science , electrical engineering , engineering , operating system
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.