331-89-5Relevant articles and documents
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Young,Zbarsky
, p. 389,394 (1944)
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Reaction of [18F]4-fluorobenzenediazonium cations with cysteine or the cysteinyl group: Preparation of 18F-labeled S-aryl-cysteine and a radiolabeled peptide
Patt,Patt
, p. 1229 - 1238 (2007/10/03)
A reaction route for the preparation of no-carrier-added (n.c.a.) [18F]S-4-fluorophenylcysteine 7 via the [18F]-4-fluorobenzenediazonium ion 4 is described. The key step in this radiosynthesis is the reaction of 4 with cysteine forming [18F]4-fluorophenyldiazocysteine 6, which is subsequently converted into 7 by irradiation with 366 nm light. 4 was synthesized by reacting 1,4-dinitrobenzene 1 with [18F]-fluoride in acetonitrile in a PEEK-capillary in a microwave oven. After dilution of the reaction mixture with methanol, the resulting [18F]4-fluoro-1-nitrobenzene 2 was submitted to reduction by means of H2 with Pd on C catalyst. The resulting [18F]4-fluoroaniline 3 was purified by HPLC and diazotized to 4. The preparation of 4 was optimized with regard to yield and purity. The radiochemical yield of 6 was > 90% (based on 3) while after UV irradiation and HPLC purification 45% of 7 (based on 3) was obtained (yields corrected for decay). The suitability of this method for labeling peptides with fluorine-18 was demonstrated by application to the tripeptide, glutathione (GSH; γ-L-glutamyl-L-cysteinyglycine) 8. Copyright
