K. Hamacher
Dec 1, 1999
Citations
2
Influential Citations
33
Citations
Journal
Journal of Labelled Compounds and Radiopharmaceuticals
Abstract
A radiosynthesis of n.c.a. (2S,4R)-4-[18F]fluoroproline (trans-configuration) and its disastereomer (2S,4S)-4-[18F]fluoroproline (cis-configuration) has been developed. It allows the routine production of up to 18 GBq of product for clinical purposes in a remote controlled system. The 18F-labelled amino acids were prepared via cryptate mediated n.c.a. nucleophilic 18F-fluorination starting from the corresponding N-Boc-4-(toluene-sulfonyloxy)proline methylester. N-deprotection and ester hydrolysis takes place under acidic conditions in presence of trifluoromethanesulfonic acid. HPLC-purification combined with on-line solid phase extraction yielded the diastereomerically pure 4-[18F]fluoroprolines within 90 min with a radiochemical yield of 36±7% (n=52). Configuration of both isomers was confirmed by comparison with standard compounds which were synthesized via fluorination of the related oxazolidinones with diethylamino sulfurtrifluoride, starting from (2S,4S)- and (2S,4R)-4-hydroxy proline, respectively. Copyright © 1999 John Wiley & Sons, Ltd.