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• W3124287972 startingPage "736" @default.
• W3124287972 abstract "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." @default.
• W3124287972 created "2021-02-01" @default.
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• W3124287972 date "2021-01-26" @default.
• W3124287972 modified "2023-09-26" @default.
• W3124287972 title "Unprotected Galactosamine as a Dynamic Key for a Cyclochiral Lock" @default.
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• W3124287972 doi "https://doi.org/10.1021/jasms.0c00437" @default.
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• W3124287972 hasPublicationYear "2021" @default.
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