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 ¹⁹F NMR singlet signal that is easily detected in an aqueous environment. In addition, the kinetics of ¹⁹F NMR relaxation processes in blood solution fit the requirements for the potential use of the new compound as a probe in ¹⁹F magnetic resonance imaging applications in translational clinical field.

开发了通过Oppolzer的苏丹草甘氨酸盐酸盐的非对映选择性苄基化方法，对非蛋白原氨基酸3,4-二羟基-L-苯丙氨酸（L-DOPA）进行全氟叔丁氧基（PFTB）标记的类似物的稳健多步合成。新化合物的特征是将PFTB连接到生物化学和药理学相关的L-DOPA支架的柔性烷氧基接头，该支架促进了氟化部分的自由运动。因此，这9个化学当量的氟原子产生了强烈而尖锐的¹⁹ F NMR单线态信号，该信号在水性环境中容易检测到。此外，血液溶液中¹⁹ F NMR弛豫过程的动力学符合将新化合物潜在用作探针的要求。¹⁹ F磁共振成像在翻译临床领域中的应用。