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Issue 20, 2010
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Synthesis and application of 4-[18F]fluorobenzylamine: A versatile building block for the preparation of PET radiotracers

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Abstract

A novel synthesis of 4-[18F]fluorobenzylamine ([18F]FBA) by means of transition metal-assisted sodium borohydride reduction of 4-[18F]fluorobenzonitrile ([18F]FBN) is described. This approach could successfully be extended to borohydride exchange resin (BER) enabling a viable option for use in automated syntheses. [18F]FBA was used for the synthesis of 4-[18F]fluorobenzylamine-based thiol group-reactive prosthetic groups 4-[18F]fluorobenzyl-2-bromoacetamide ([18F]FBBA) and 4-[18F]fluorobenzylamidopropionyl maleimide ([18F]FBAPM). [18F]FBBA and [18F]FBAPM were obtained in radiochemical yields of 75% and 55%, respectively. Feasibility of using [18F]FBAPM as novel prosthetic group for peptide and protein labelling was demonstrated with cysteine-containing tripeptide glutathione (GSH). [18F]FBBA was used for labelling of a fully phosphorothioated 20mer oligodesoxynucleotide (ODN).

Graphical abstract: Synthesis and application of 4-[18F]fluorobenzylamine: A versatile building block for the preparation of PET radiotracers

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Publication details

The article was received on 14 Jun 2010, accepted on 16 Jul 2010 and first published on 25 Aug 2010


Article type: Paper
DOI: 10.1039/C0OB00255K
Citation: Org. Biomol. Chem., 2010,8, 4730-4735
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    Synthesis and application of 4-[18F]fluorobenzylamine: A versatile building block for the preparation of PET radiotracers

    I. Koslowsky, J. Mercer and F. Wuest, Org. Biomol. Chem., 2010, 8, 4730
    DOI: 10.1039/C0OB00255K

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