Chiral separation by a terminal chirality triggered P-helical quinoline oligoamide foldamer

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Abstract

A P-helical quinoline oligoamide foldamer was grafted on silica and applied as an HPLC stationary phase for chiral separation. The P-handedness of the quinoline oligoamide foldamer was induced by a (1S)-camphanyl group, which was introduced at the N-terminus of a tetrameric quinoline oligoamide foldamer (Cmp-Q 4 ). To immobilize the foldamer on porous silica particles, a trimethoxysilyl group was introduced at the opposing end of the foldamer. Elemental analysis indicated that the amount of foldamer on the silica surface was 0.57 μmol/m 2 . Circular dichroism and vibrational CD spectra of Cmp-Q 4 and Cmp-Q 4 -immobilized silica (Sil-Q 4 -Cmp) suggested that the helical structure of Cmp-Q 4 was altered on the silica surface whilst retaining a chiral structure. The chiral recognition ability of Sil-Q 4 -Cmp was evaluated with various aromatic enantiomers. Sil-Q 4 -Cmp showed enantio-selectivity for axially chiral molecules (e.g., α Trigger's base = 1.26 and α Binaphthol = 1.07). Sil-Q 4 -Cmp showed remarkable recognition of helical octameric quinoline oligoamides with isobutoxy and triethylene glycol side chains (α = 10.35 and 14.98, respectively). In contrast, an (1S)-camphanyl group-immobilized porous silica showed no chiral recognition for any enantiomers tested in this study. To elucidate the chiral separation mechanism of Sil-Q 4 -Cmp, thermodynamic parameters were calculated using van't Hoff plots. HPLC results and thermodynamic parameters suggested that the chiral recognition of Sil-Q 4 -Cmp is based on the helical structure of Cmp-Q 4 and other thermally dependent interactions such as hydrophobic effects associated with aromatic stacking. This work represents the first known application of aromatic foldamers in chiral separation.

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Noguchi, H., Takafuji, M., Maurizot, V., Huc, I., & Ihara, H. (2016). Chiral separation by a terminal chirality triggered P-helical quinoline oligoamide foldamer. Journal of Chromatography A, 1437, 88–94. https://doi.org/10.1016/j.chroma.2016.01.059

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