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Issue 3, 2011
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Enantiospecific synthesis of 2-[18F]fluoro-L-phenylalanine and 2-[18F]fluoro-L-tyrosine by isotopic exchange

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Abstract

2-[18F]Fluoro-L-phenylalanine and 2-[18F]fluoro-L-tyrosine have been developed as promising radiopharmaceuticals for molecular imaging using positron emission tomography (PET). However, the lack of a convenient radiosynthetic pathway has limited their practical use. In this work a new three-step nucleophilic synthesis of these compounds starting from [18F]fluoride is described. Corresponding precursors (1a and 1b) were 18F-fluorinated by isotopic exchange, followed by the removal of an activating formyl group with Rh(PPh3)3Cl and subsequent hydrolysis of protecting groups in acidic medium. All reactions were carried out using both conventional and microwave heating. Conventional heated reactions yielded the desired products 2-[18F]Fphe and 2-[18F]Ftyr in 43% and 49% whereas radiochemical yields of 34% and 43%, respectively, were obtained when they were heated by microwaves. Under optimized conditions the enantiomeric purity was ≥94% for both radiopharmaceuticals.

Graphical abstract: Enantiospecific synthesis of 2-[18F]fluoro-l-phenylalanine and 2-[18F]fluoro-l-tyrosine by isotopic exchange

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Publication details

The article was received on 16 Jul 2010, accepted on 04 Oct 2010 and first published on 19 Nov 2010


Article type: Paper
DOI: 10.1039/C0OB00440E
Citation: Org. Biomol. Chem., 2011,9, 765-769
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    Enantiospecific synthesis of 2-[18F]fluoro-L-phenylalanine and 2-[18F]fluoro-L-tyrosine by isotopic exchange

    J. Castillo Meleán, J. Ermert and H. H. Coenen, Org. Biomol. Chem., 2011, 9, 765
    DOI: 10.1039/C0OB00440E

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