Organic & Biomolecular Chemistry 2010-10-21

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

Ingrid Koslowsky, John Mercer, Frank Wuest

Index: Org. Biomol. Chem. 8(20) , 4730-5, (2010)

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Abstract

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