Unprotected Galactosamine as a Dynamic Key for a Cyclochiral Lock.

Fraschetti C, Letzel MC, Paletta M, Mattay J, Crestoni ME, Chiavarino B, Filippi A (2021)
Journal of the American Society for Mass Spectrometry.

Zeitschriftenaufsatz | E-Veröff. vor dem Druck | Englisch
 
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Autor*in
Fraschetti, Caterina; Letzel, Matthias C; Paletta, MarleneUniBi; Mattay, JochenUniBi; Crestoni, Maria Elisa; Chiavarino, Barbara; Filippi, Antonello
Abstract / Bemerkung
The discrimination of d-galactosamine (G), representative of the amino-sugar class of compounds, has been probed through nano-ESI-FT-ICR mass spectrometry by isolating the relevant [C·H·G]+ proton-bound complexes with the enantiomers of the cyclochiral resorcin[4]arene C and allowing them to react toward three primary amines (B = EtNH2, iPrNH2, and (R)- and (S)-sBuNH2). The system under investigation presents several features that help to unveil the behavior of unprotected G in such a supramolecular architecture: (i) the hydrophobic derivatization of the C convex side forces the polar guest G to be coordinated by the cyclochiral concave region; (ii) protonated d-galactosamine exists as an anomeric mixture, dynamically interconverting throughout the experimental time-window; and (iii) different basicities of B allow the experiment to subtly tune the reactivity of the [C·H·G]+ complexes. Three [C·H·G]+ aggregate-types were found to exist, differing in both their origin and reactivity. The most reactive adducts ([C·H·G]ESI+), generated in the electrospray environment, undergo a G-to-B ligand exchange in competition with a partial isomerization to the unreactive [C·H·G]GAS+-type complexes. Finally, the poorly reactive [C·H·G]SOL+ aggregates are formed in solution over an hours-long time scale. A cyclochirality effect on the reactivity was found to depend on the considered [C·H·G]+ aggregate-type.
Erscheinungsjahr
2021
Zeitschriftentitel
Journal of the American Society for Mass Spectrometry
eISSN
1879-1123
Page URI
https://pub.uni-bielefeld.de/record/2951150

Zitieren

Fraschetti C, Letzel MC, Paletta M, et al. Unprotected Galactosamine as a Dynamic Key for a Cyclochiral Lock. Journal of the American Society for Mass Spectrometry. 2021.
Fraschetti, C., Letzel, M. C., Paletta, M., Mattay, J., Crestoni, M. E., Chiavarino, B., & Filippi, A. (2021). Unprotected Galactosamine as a Dynamic Key for a Cyclochiral Lock. Journal of the American Society for Mass Spectrometry. doi:10.1021/jasms.0c00437
Fraschetti, C., Letzel, M. C., Paletta, M., Mattay, J., Crestoni, M. E., Chiavarino, B., and Filippi, A. (2021). Unprotected Galactosamine as a Dynamic Key for a Cyclochiral Lock. Journal of the American Society for Mass Spectrometry.
Fraschetti, C., et al., 2021. Unprotected Galactosamine as a Dynamic Key for a Cyclochiral Lock. Journal of the American Society for Mass Spectrometry.
C. Fraschetti, et al., “Unprotected Galactosamine as a Dynamic Key for a Cyclochiral Lock.”, Journal of the American Society for Mass Spectrometry, 2021.
Fraschetti, C., Letzel, M.C., Paletta, M., Mattay, J., Crestoni, M.E., Chiavarino, B., Filippi, A.: Unprotected Galactosamine as a Dynamic Key for a Cyclochiral Lock. Journal of the American Society for Mass Spectrometry. (2021).
Fraschetti, Caterina, Letzel, Matthias C, Paletta, Marlene, Mattay, Jochen, Crestoni, Maria Elisa, Chiavarino, Barbara, and Filippi, Antonello. “Unprotected Galactosamine as a Dynamic Key for a Cyclochiral Lock.”. Journal of the American Society for Mass Spectrometry (2021).

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