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Synthesis of [ 14 C]‐N‐[(trimethylamineboryl) carbonyl]‐phenylalanine‐methyl ester
Author(s) -
Miller Merrill C.,
Wyrick Steven D.,
Hall Iris H.,
Sood Anup,
Spielvogel Bernard F.
Publication year - 1992
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580310805
Subject(s) - chemistry , dipeptide , phenylalanine , triethylamine , hydrochloride , salt (chemistry) , amino acid , acetonitrile , molecule , chemical synthesis , trimethylamine , organic chemistry , medicinal chemistry , stereochemistry , in vitro , biochemistry
Reported is the synthesis of [ 14 C]‐L‐N‐[(trimethylamineboryl)carbonyl]‐phenylalanine methyl ester, a boron containing α‐amino acid dipeptide analog with anti‐neoplastic, anti‐inflammatory, and hypolipidemic activities. The 14 C label is universally distributed among all carbon positions of the phenylalanine portion of the molecule. Briefly, the dipeptide is prepared by reacting the phenylalanine methyl ester hydrochloride salt with trimethylamine‐carboxyborane, triphenylphospine (TPP), CCl 4 , and triethylamine (TEA) in acetonitrile, for 24 hours. The final product afforded a specific activity of 5.71 mCi/mmol.