Premium
Controlling Helix Handedness in Water‐Soluble Quinoline Oligoamide Foldamers
Author(s) -
Dawson Simon J.,
Mészáros Ádám,
Pethő Lilla,
Colombo Cinzia,
Csékei Márton,
Kotschy András,
Huc Ivan
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402247
Subject(s) - chemistry , quinoline , moiety , monomer , helix (gastropod) , diastereomer , water soluble , aqueous solution , solubility , stereochemistry , combinatorial chemistry , crystallography , organic chemistry , polymer , ecology , snail , biology
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.