Cyclochiral resorcin[4]arenes as effective enantioselectors in the gas phase

Fraschetti C, Letzel M, Paletta M, Mattay J, Speranza M, Filippi A, Aschi M, Rozhenko AB (2012)
Journal of Mass Spectrometry 47(1): 72-78.

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Abstract
The effect of cyclochirality of rccc-2,8,14,20-tetra-n-decyl-4,10,16,22-tetra-O-methylresorcin[4]arene (C) on the enantiodiscrimination of a number of chiral bidentate and tridentate aromatic and aliphatic biomolecules (G) has been investigated by nano-electrospray ionization (nano-ESI)-Fourier transform ion cyclotron resonance mass spectrometry. The experimental approach is based on the formation of diastereomeric proton-bound [C center dot H center dot G](+) complexes by nano-ESI of solutions containing an equimolar amount of quasi-enantiomers (C) together with the chiral guest (G) and the subsequent measurement of the rate of the G substitution by the attack of several achiral and chiral amines. In general, the heterochiral complexes react faster than the homochiral ones, except when G is an aminoalcoholic neurotransmitter whose complexes, beyond that, exhibit the highest enantioselectivity. The kinetic results were further supported by both collision-induced dissociation experiments on some of the relevant [C-2 center dot H center dot G](+) three-body species and Density functional theory (DFT) calculations performed on the most selective systems. Copyright (C) 2012 John Wiley & Sons, Ltd.
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Fraschetti C, Letzel M, Paletta M, et al. Cyclochiral resorcin[4]arenes as effective enantioselectors in the gas phase. Journal of Mass Spectrometry. 2012;47(1):72-78.
Fraschetti, C., Letzel, M., Paletta, M., Mattay, J., Speranza, M., Filippi, A., Aschi, M., et al. (2012). Cyclochiral resorcin[4]arenes as effective enantioselectors in the gas phase. Journal of Mass Spectrometry, 47(1), 72-78.
Fraschetti, C., Letzel, M., Paletta, M., Mattay, J., Speranza, M., Filippi, A., Aschi, M., and Rozhenko, A. B. (2012). Cyclochiral resorcin[4]arenes as effective enantioselectors in the gas phase. Journal of Mass Spectrometry 47, 72-78.
Fraschetti, C., et al., 2012. Cyclochiral resorcin[4]arenes as effective enantioselectors in the gas phase. Journal of Mass Spectrometry, 47(1), p 72-78.
C. Fraschetti, et al., “Cyclochiral resorcin[4]arenes as effective enantioselectors in the gas phase”, Journal of Mass Spectrometry, vol. 47, 2012, pp. 72-78.
Fraschetti, C., Letzel, M., Paletta, M., Mattay, J., Speranza, M., Filippi, A., Aschi, M., Rozhenko, A.B.: Cyclochiral resorcin[4]arenes as effective enantioselectors in the gas phase. Journal of Mass Spectrometry. 47, 72-78 (2012).
Fraschetti, Caterina, Letzel, Matthias, Paletta, Marlene, Mattay, Jochen, Speranza, Maurizio, Filippi, Antonello, Aschi, Massimiliano, and Rozhenko, Alexander B. “Cyclochiral resorcin[4]arenes as effective enantioselectors in the gas phase”. Journal of Mass Spectrometry 47.1 (2012): 72-78.
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Synthesis and conformational studies of chiral macrocyclic [1.1.1]metacyclophanes containing benzofuran rings.
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PMID: 26220058

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