title: 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 (129)Xe NMR-based biosensors. We show that the cryptophane-223 skeleton can be modified to introduce a unique secondary alcohol to the propylenedioxy linker. This chemical functionality can then be exploited to introduce a functional group that is 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, two molecular platforms have been prepared, and the ability of these new derivatives to bind xenon has been investigated.
authors.affiliation: †Laboratoire de Chimie de l'ENS LYON, UMR 5182 - CNRS, École Normale Supérieure de Lyon, 46 Allée d'Italie, 69364 Lyon, France.
authors.forename: Laure-Lise
authors.initials: LL
authors.lastname: Chapellet
authors.affiliation: †Laboratoire de Chimie de l'ENS LYON, UMR 5182 - CNRS, École Normale Supérieure de Lyon, 46 Allée d'Italie, 69364 Lyon, France.
authors.forename: James R
authors.initials: JR
authors.lastname: Cochrane
authors.affiliation: ‡Laboratoire Structure et Dynamique par Résonance Magnétique, CEA Saclay, IRAMIS, NIMBE UMR CEA/CNRS 3685, 91191 Gif sur Yvette, France.
authors.forename: Emilie
authors.initials: E
authors.lastname: Mari
authors.affiliation: ‡Laboratoire Structure et Dynamique par Résonance Magnétique, CEA Saclay, IRAMIS, NIMBE UMR CEA/CNRS 3685, 91191 Gif sur Yvette, France.
authors.forename: Céline
authors.initials: C
authors.lastname: Boutin
authors.affiliation: ‡Laboratoire Structure et Dynamique par Résonance Magnétique, CEA Saclay, IRAMIS, NIMBE UMR CEA/CNRS 3685, 91191 Gif sur Yvette, France.
authors.forename: Patrick
authors.initials: P
authors.lastname: Berthault
authors.affiliation: †Laboratoire de Chimie de l'ENS LYON, UMR 5182 - CNRS, École Normale Supérieure de Lyon, 46 Allée d'Italie, 69364 Lyon, France.
authors.forename: Thierry
authors.initials: T
authors.lastname: Brotin
mesh_terms: D015374:Biosensing Techniques; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013329:Structure-Activity Relationship; D014978:Xenon / Q000737:chemistry*
chemical_list: D011083:Polycyclic Compounds; C523242:cryptophane; D014978:Xenon