Trifluoromethanesulfonic acid, an alternative solvent medium for the direct electrophilic fluorination of DOPA: new syntheses of 6‐[18F]fluoro‐L‐DOPA and 6‐[18F]fluoro‐D‐DOPA Journal Articles uri icon

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abstract

  • AbstractPrevious work from this laboratory has shown that the direct fluorination of 3, 4‐dihydroxy‐phenyl‐L‐alanine (L‐DOPA) in anhydrous HF (aHF) or BF3/HF with F2 is an efficient method for the synthesis of 6‐fluoro‐L‐DOPA. Since then, 18F‐labeled 6‐fluoro‐L‐DOPA ([18F]6‐fluoro‐L‐DOPA) has been used to study presynaptic dopaminergic function in the human brain and to monitor gastrointestinal carcinoid tumors.This work demonstrates that the reactivity and selectivity of F2 toward L‐DOPA in CF3SO3H is comparable with that in aHF. This new synthetic procedure has led to the production of [18F]fluoro‐L‐DOPA and [18F]fluoro‐D‐DOPA isomers in 17±2% radiochemical yields (decay corrected with respect to [18F]F2). The 2‐ and 6‐FDOPA isomers were separated by HPLC and subsequently characterized by 19F NMR spectroscopy. The corresponding [18F]‐FDOPA enantiomers have been obtained in clinically useful quantities by a synthetic approach that avoids the use of aHF. Copyright © 2007 John Wiley & Sons, Ltd.

publication date

  • December 2007