Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Synthesis of Corticotropin Peptides. XIII. The Synthesis of a Hexacosapeptide and a Heptacosapeptide Corresponding to the First Twenty-six and Twenty-seven Amino Acid Residues of Corticotropin (ACTH)
Ken InouyeYoshie SumitomoMasaru Shin
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1976 Volume 49 Issue 12 Pages 3620-3628

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Abstract

The syntheses are described of a hexacosapeptide H–Ser–Tyr–Ser–Met–Glu–His–Phe–Arg–Trp–Gly–Lys–Pro–Val–Gly–Lys–Lys–Arg–Arg–Pro–Val–Lys–Val–Tyr–Pro–Asn–Gly–OH (I) and a heptacosapeptide H–Ser–Tyr–Ser–Met–Glu–His–Phe–Arg–Trp–Gly–Lys–Pro–Val–Gly–Lys–Lys–Arg–Arg–Pro–Val–Lys–Val–Tyr–Pro–Asn–Gly–Ala–OH (II) corresponding to the first twenty-six and twenty-seven amino acid residues, respectively, of corticotropin (ACTH), in which a new protecting group 1-methylcyclohexyloxycarbonyl (Mhoc) is utilized for the temporary protection of the ε-amino function of lysines. The in vivo steroidogenic potencies of the synthetic peptides I and II are compared on a molar basis with those of ACTH(1–18)-NH2 and synthetic human ACTH (αh-ACTH) to demonstrate that the relative potencies of I and II vs. ACTH(1–18)–NH2 are 2.3 and 2.3–3.8, respectively, and those vs. αh-ACTH are 1.1 and 1.1–1.8, respectively.

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