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Synthesis of [14C]-N-[(trimethylamineboryl) carbonyl]-phenylalanine-methyl ester

✍ Scribed by Merrill C. Miller; Steven D. Wyrick; Iris H. Hall; Anup Sood; Bernard F. Spielvogel


Publisher
John Wiley and Sons
Year
1992
Tongue
French
Weight
166 KB
Volume
31
Category
Article
ISSN
0022-2135

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✦ Synopsis


Abstract

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.


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