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

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Arginylmethionine was prepared by three different methods, one from N^α-benzyloxycarbonyl-N^G-tosylarginylmethionine with sodium in liquid ammonia and others, from N^α-benzyloxycarbonyl-N^G-nitroarginylmethionine by treatment with hydrogen fluoride, and from N^α-t-butoxycarbonyl-N^G-nitroarginylmethionine by treatment with stannous chloride in 80% formic acid. Arginylmethionine was coupled with N^α-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.