Tetrahedron p. 2635 - 2658 (1992)
Update date:2022-07-29
Topics: Mass spectrometry (MS) Click Chemistry Photoaffinity labeling Receptor binding assay Photoaffinity probe
Suzuki, Masaaki
Koyano, Hiroshi
Noyori, Ryoji
Hashimoto, Hitoshi
Negishi, Manabu
Ichikawa, Atsushi
Ito, Seiji
A stable prostacyclin analogue, (15S)-18c, having an azidophenyl group as a photoaffinity labeling functionality has been synthesized. This compound has a sufficiently high affinity to the prostacyclin receptor protein in mastocytoma P-815 cells, exhibiting an IC50 value of 3 nM for the replacement of iloprost bound to the receptor protein. A photoaffinity probe compound, [3H]-(15S)-18c, is obtainable by reduction of the ketone 16c with [3H]NaBH4 - CeCl3 followed by alkaline hydrolysis of the methyl ester.
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