NOVEL SYNTHESIS OF 2-SELENIENYLALANINE

A novel synthesis of 2-selenienylalanine [2-amino-3-(selenophen-2'-yl)propanoic acid] was designed to permit the insertion of selenium late in the synthetic pathway so that a subsequent synthesis using selenium-75 would maximize the radiochemical yield while minimizing radiation exposure of the chemist. The coupling of N-acetyl-propargylglycine ethyl ester with trimethylsilylacetylene in the presence of Hay's catalyst gave ethyl N-acetyl-2-amino-7-(trimethylsilyl)-4,6-heptadiynoate in 57% yield. This product was reacted with sodium hydrogen selenide which was prepared from selenium metal and sodium borohydride, and 2-selenienylalanine was generated in 33% yield. Copyright © 1979, American Chemical Society. All rights reserved.