A metal-templated synthesis of precursors of (2S)- and (2R)-2-(3-[18F]fluoropropyl)-tyrosine as potential radiotracers for positron emission tomographyстатьяИсследовательская статья
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Дата последнего поиска статьи во внешних источниках: 10 июля 2024 г.
Аннотация:The development of new amino acid-based radiotracers for positron emission tomography (PET) imaging is an important but challenging area in organic synthetic chemistry. Herein, we report the asymmetric metal-templated synthesis of (2S)- and (2R)-2-(3-[19F]fluoropropyl)-tyrosine (Tyr), which serves as a reference for a 18F-labeled Tyr derivative as well as its precursors. Using a chiral Ni(II) complex of the Schiff base derived from (S)-2-[N-(N’-benzylprolyl)amino]benzaldehyde (BBA) and racemic Tyr as the initial substrate, we obtained the desired Ni(II) complexes with the (2S)- and (2R)-2-(3-[19F]fluoropropyl)-Tyr appendages by following these steps: 1) alkylation of the α-carbon atom of Tyr motif with acrolein; 2) reduction of the aldehyde group using NaBH4; 3) protection of the hydroxyl group with the mesyl (Ms) group and finally 4) nucleophilic substitution of the OMs group with a 19F atom using anhydrous KF.