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Solution Structure of Quinoline- and Pyridine-Derived Oligoamide Foldamers

Chemistry : a European journal, 2005-10, Vol.11 (21), p.6135-6144 [Peer Reviewed Journal]

Copyright © 2005 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim ;ISSN: 0947-6539 ;EISSN: 1521-3765 ;DOI: 10.1002/chem.200500395 ;PMID: 16075439

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Title:
Solution Structure of Quinoline- and Pyridine-Derived Oligoamide Foldamers
Author: Dolain, Christel ; Grélard, Axelle ; Laguerre, Michel ; Jiang, Hua ; Maurizot, Victor ; Huc, Ivan
Subjects: Amides - chemical synthesis ; Amides - chemistry ; conformation analysis ; Crystallography, X-Ray ; Cyclization ; helical structures ; Magnetic Resonance Spectroscopy ; Models, Chemical ; Molecular Conformation ; molecular dynamics ; NMR spectroscopy ; Oligopeptides - chemical synthesis ; Oligopeptides - chemistry ; Pyridines - chemical synthesis ; Pyridines - chemistry ; Quinolones - chemical synthesis ; Quinolones - chemistry ; Structure-Activity Relationship ; supramolecular chemistry
Is Part Of: Chemistry : a European journal, 2005-10, Vol.11 (21), p.6135-6144
Description: The unambiguous elucidation of a new folded structure in solution may prove to be a very challenging task. The NMR protocols developed for solving the solution structures of α‐peptides have been applied to aliphatic β‐ and γ‐peptides but are not directly applicable to aromatic oligomers. In particular, the string of spin systems in an aromatic sequence cannot be reconstituted solely from correlations between protons. For aromatic oligomers, it is shown that the assignment of a large part of the 13C NMR spectrum through HMBC and HSQC experiments allows to unambiguously assign proton NMR spectra and in turn to interpret NOE correlations. This has been implemented both with quinoline‐ and pyridine‐derived oligoamide foldamers, and should be applicable to a wide range of oligomers including various combinations of monomers. The NOE correlations allow the unambiguous solution structure elucidation of helical conformations of oligoamides derived from pyridine and quinoline monomers showing that, in these series, the solution structures correspond very well to the structures observed in the solid state. It matches! Are solid‐state conformations and solution conformations identical? A new NMR protocol has allowed the full assignment of NMR spectra of helical aromatic amide foldamers derived from quinoline (right) or pyridine (left) and allows to unambiguously determine their solution structure and compare them with structures obtained in the solid state.
Publisher: Weinheim: WILEY-VCH Verlag
Language: English
Identifier: ISSN: 0947-6539
EISSN: 1521-3765
DOI: 10.1002/chem.200500395
PMID: 16075439
Source: MEDLINE
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Solution Structure of Quinoline- and Pyridine-Derived Oligoamide Foldamers

Copyright © 2005 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim ;ISSN: 0947-6539 ;EISSN: 1521-3765 ;DOI: 10.1002/chem.200500395 ;PMID: 16075439

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