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A Sulfonated Tweezer-Shaped Receptor Selectively Recognizes Caffeine in Water.


ABSTRACT: The selective recognition of caffeine in water among structurally related xanthines and purine or pyrimidine bases was achieved by a simple tweezer-shaped receptor featuring sulfonate hydrosolubilizing groups. The remarkable affinity for caffeine, among the highest reported thus far in the literature and larger than that shown by adenosine receptors of all subtypes, stems from a synergistic combination of hydrogen bonding, CH-π, and π-stacking interactions.

SUBMITTER: Francesconi O 

PROVIDER: S-EPMC8902752 | biostudies-literature | 2022 Mar

REPOSITORIES: biostudies-literature

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A Sulfonated Tweezer-Shaped Receptor Selectively Recognizes Caffeine in Water.

Francesconi Oscar O   Ienco Andrea A   Papi Francesco F   Dolce Marta M   Catastini Andrea A   Nativi Cristina C   Roelens Stefano S  

The Journal of organic chemistry 20220202 5


The selective recognition of caffeine in water among structurally related xanthines and purine or pyrimidine bases was achieved by a simple tweezer-shaped receptor featuring sulfonate hydrosolubilizing groups. The remarkable affinity for caffeine, among the highest reported thus far in the literature and larger than that shown by adenosine receptors of all subtypes, stems from a synergistic combination of hydrogen bonding, CH-π, and π-stacking interactions. ...[more]

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