Controlling Helix Handedness in Water-Soluble Quinoline Oligoamide Foldamers

For biological applications, the control of the helix handedness of water‐soluble quinoline‐based oligoamide foldamers has been investigated by the installation of chiral end groups at either the C or N terminus. This has resulted in the development of monomer units capable of unequivocally inducing...

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Bibliographic Details
Published in:European journal of organic chemistry 2014-07, Vol.2014 (20), p.4265-4275
Main Authors: Dawson, Simon J., Mészáros, Ádám, Pethő, Lilla, Colombo, Cinzia, Csékei, Márton, Kotschy, András, Huc, Ivan
Format: Article
Language:English
Subjects:
Chemical Sciences
Chirality
Conformation analysis
Foldamers
Helical structures
Oligoamides
Organic chemistry
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Summary:For biological applications, the control of the helix handedness of water‐soluble quinoline‐based oligoamide foldamers has been investigated by the installation of chiral end groups at either the C or N terminus. This has resulted in the development of monomer units capable of unequivocally inducing helical sense without impacting the aqueous solubility. Furthermore, we showed that very slow helix handedness inversion in water can be exploited. The incorporation of a chiral moiety with no handedness‐induction properties allows the chromatographic separation of P and M helices as diastereoisomers with kinetically locked handedness. The control of the helix handedness of water‐soluble quinoline‐based oligoamide foldamers has been investigated by the installation of chiral end groups at either the N or C terminus. This has respectively afforded either quantitative induction of handedness or the ability to separate kinetically locked P and M helices as diastereoisomers.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201402247