Synthesis of 2(S)-benzyl-3-[hydroxy(1'(R)-amino ethyl)phosphinyl]propanoyl-L3-[125I]-iodotyrosine: A radiolabelled inhibitor of aminopeptidase N

Article abstract of DOI:10.1002/(SICI)1099-1344(200002)43:2<103::AID-JLCR294>3.0.CO;2-I

2(S)-benzyl-3-[hydroxy(1'(R)-aminoethyl)phosphinyl]propanoyl-L-3-[¹²⁵I]-iodo tyrosine was prepared from 1(R)-(N-benzyloxycarbonylamino)ethylphosphinic acid in a six step synthesis. This new iodinated compound, which is a highly efficient aminopeptidase N inhibitor (Ki = 0.95 nM), can be used for complete characterization of the biochemical and pharmacological properties of aminopeptidase N and its in vivo inhibition. A high radiochemical purity was obtained with a specific activity of 2.17 Ci/mmol at the end of the synthesis.