The robust multistep synthesis of a perfluoro-tert-butoxy (PFTB) tagged analogue of the non-proteinogenic amino acid 3,4-dihydroxy-L-phenylalanine (L-DOPA) via diastereoselective benzylation of Oppolzer's sultam glycinate was developed. The new compound is characterized by a flexible alkoxy linker connecting PFTB to the biochemically and pharmacologically relevant L-DOPA scaffold, which facilitates the free motion of the fluorinated moiety. Therefore, the nine chemically equivalent fluorine atoms give rise to an intense and sharp F NMR singlet signal that is easily detected in an aqueous environment. In addition, the kinetics of F NMR relaxation processes in blood solution fit the requirements for the potential use of the new compound as a probe in F magnetic resonance imaging applications in translational clinical field.
Synthesis and 19F NMR parameters of a perfluoro-tert-butoxy tagged L-DOPA analogue
Orlandi, Simonetta;Cavazzini, Marco;Capuani, Silvia;Pozzi, Gianluca
2020
Abstract
The robust multistep synthesis of a perfluoro-tert-butoxy (PFTB) tagged analogue of the non-proteinogenic amino acid 3,4-dihydroxy-L-phenylalanine (L-DOPA) via diastereoselective benzylation of Oppolzer's sultam glycinate was developed. The new compound is characterized by a flexible alkoxy linker connecting PFTB to the biochemically and pharmacologically relevant L-DOPA scaffold, which facilitates the free motion of the fluorinated moiety. Therefore, the nine chemically equivalent fluorine atoms give rise to an intense and sharp F NMR singlet signal that is easily detected in an aqueous environment. In addition, the kinetics of F NMR relaxation processes in blood solution fit the requirements for the potential use of the new compound as a probe in F magnetic resonance imaging applications in translational clinical field.| File | Dimensione | Formato | |
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Descrizione: This is the Submitted Manuscript of the article published in J. Fluorine Chem. 2020, 237, 109596; https://doi.org/10.1016/j.jfluchem.2020.109596
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Descrizione: Synthesis and 19F NMR parameters of a perfluoro-tert-butoxy tagged L-DOPA analogue
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