Synthesis of a tritium labeled tetrafluoro-substituted aryl azide photoaffinity labeling agent for chloride channels. Application of [3H]-sodium borohydride-cobalt chloride to tritium labeling
✍ Scribed by Bruce R. Branchini; Elizabeth W. Adams; Laura A. Egan; Martha H. Murtiashaw
- Publisher
- John Wiley and Sons
- Year
- 1992
- Tongue
- French
- Weight
- 451 KB
- Volume
- 31
- Category
- Article
- ISSN
- 0022-2135
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✦ Synopsis
Abstract
5‐Nitro‐2‐[N‐3‐(4‐azido‐2,3,5,6‐tetrafluorophenyl)‐propylamino]‐benzoic acid (FAzNPPB), a photoaffinity analog of the potent epithelial chloride channel blocker 5‐nitro‐2‐(3‐phenylpropylamino)‐benzoic acid (NPPB) has been prepared in five steps from commercially available 4‐amino‐2,3,5,6‐tetrafluorobenzonitrile. The main feature of this synthesis was the use of NaBH~4~‐CoCl~2~ to convert an aryl‐substituted alkenyl nitrile precursor to the corresponding alkyl amine. The feasibility of this approach and the stoichiometry were developed by model work with cinnamonitrile. Using sodium borotritide‐cobalt chloride, [^3^H]‐FAzNPPB (specific activity 13.9 mCi/mmol, radiochemical purity >99%) was prepared in three steps from (E)‐4‐amino‐2,3,5,6‐tetrafluorocinnamonitrile.