Studies on Peptides. XV. Synthesis of Prolyltyrosylarginylmethionine, the Tetrapeptide situated within the Amino Acid Sequences of Monkey and Human β-Melanocyte-stimulating Hormones.

Abstract
Arginylmethionine was prepared by three different methods, one from Nα-benzyloxycarbonyl-NG-tosylarginylmethionine with sodium in liquid ammonia and others, from Nα-benzyloxycarbonyl-NG-nitroarginylmethionine by treatment with hydrogen fluoride, and from Nα-t-butoxycarbonyl-NG-nitroarginylmethionine by treatment with stannous chloride in 80% formic acid. Arginylmethionine was coupled with Nα-t-butoxycarbonylprolyltyrosine via the azide method and the resulting peptide was treated with trifluoroacetic acid to give prolyltyrosylarginylmethionine, the tetrapeptide situated within the structures of monkey and human β-melanocyte-stimulating hormones.

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