Synthesis of the Heptadecapeptide Corresponding to the Entire Amino Acid Sequence of Salmon Melanin-Concentrating Hormone (MCH)

Abstract

The heptadecapeptide corresponding to the entire amino acid sequence of melanin-concentrating hormone (MCH), isolated from chum salmon pituitaries, was synthesized by successive condensation of four peptide fragments and the N-terminal amino acid, i.e., Boc-(14—17)-OBzl, Boc-(9—13)-OH, Boc-(5—8)-NHNH2 Boc-(2—4)-NHNH2 and Boc-Asp(OBzl)-OH, followed by deprotection with 1 M trifluoromethanesulfonic acid-thioanisole in trifluoro-acetic acid (TFA) and disulfide formation through the S-sulfonate. When melanin-concentrating activity was measured on a tilapia scale, the minimum effective concentration of the synthetic peptide was equivalent to that of natural salmon MCH (1 nM). © 1984, The Pharmaceutical Society of Japan. All rights reserved.