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Synthesis of cryptophanes With Two Different Reaction Sites: Chemical Platforms for Xenon Biosensing

Abstract : We report the synthesis of new water-soluble cryptophane host molecules that can be used for the preparation of 129Xe NMR-based biosensors. We show that the cryptophane-223 skeleton can be modified in order to introduce a unique secondary alcohol to the propylenedioxy linker. This chemical functionality can then be exploited to introduce a functional group different from the six chemical groups attached to the aromatic rings. In this approach the generation of a statistical mixture when trying to selectively functionalize a symmetrical host molecule is eliminated, which enables the efficient large-scale production of new cryptophanes that can be used as chemical platforms ready to use for the preparation of xenon biosensors. To illustrate this approach molecular platforms 1 and 2 have been prepared. The ability of these new derivatives to bind xenon has also been investigated.
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https://hal.archives-ouvertes.fr/hal-01187801
Contributor : Serge Palacin <>
Submitted on : Thursday, August 27, 2015 - 4:50:22 PM
Last modification on : Monday, February 10, 2020 - 6:12:48 PM

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Laure-Lise Chapellet, James Robert Cochrane, Emilie Mari, Céline Boutin, Patrick Berthault, et al.. Synthesis of cryptophanes With Two Different Reaction Sites: Chemical Platforms for Xenon Biosensing. Journal of Organic Chemistry, American Chemical Society, 2015, 80, pp.6143-6151. ⟨10.1021/acs.joc.5b00653⟩. ⟨hal-01187801⟩

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