Synthesis and Binding Properties of 2-Amino-5-phosphono-3-pentenoic Acid Photoaffinity Ligands as Probes for the Glutamate Recognition Site of the NMDA Receptor

Article abstract of DOI:10.1021/jm00075a029

Four ω-benzoylated (E)-2,10-diamino-4-(phosphonomethyl)dec-3-enoic acids have been synthesized and tested in vitro for binding to the glutamate recognition site of the NMDA (N-methyl-D-aspartate) receptor.The ω-4-azidosalicylamide derivative 24 was iodinated to give the photoaffinity ligand 25 (CGP 55802 A) which showed an IC50 value of 34 nM in the in vitro <³H>CGP 39653 binding assay.This compound and its radioactive 125I-form are the first photoaffinity ligands for the NMDA receptor with high affinity to the glutamate recognition site.