Synthesis of Thyrotropin-Releasing Hormone-Related Peptides Using Nα-tert-Bytyloxycarbonyl-ω-(N-tert-butyloxycarbonylcarbamoyl)-α-amino Acids

Naoki SAKURA; Kyoko HIROSE; Miwako NISHIJIMA; Tadashi HASHIMOTO; Takasi OKABE; Chiaki MIYAMORI; Tamotsu SATO

doi:10.1248/cpb.37.3125

Synthesis of Thyrotropin-Releasing Hormone-Related Peptides Using N^α-tert-Bytyloxycarbonyl-ω-(N-tert-butyloxycarbonylcarbamoyl)-α-amino Acids

Naoki SAKURA, Kyoko HIROSE, Miwako NISHIJIMA, Tadashi HASHIMOTO, Takasi OKABE, Chiaki MIYAMORI, Tamotsu SATO

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Keywords: pyrohomoglutamylpeptide, δ-lactam formation, N^α, N^ca-di-tert-butyloxycarbonylhomoglutamine, [pHgu¹, Nva²]-TRH, central nervous system effect, TRH receptor assay, HPLC alumina support

JOURNAL FREE ACCESS

1989 Volume 37 Issue 11 Pages 3125-3127

DOI https://doi.org/10.1248/cpb.37.3125

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Abstract

Application of N^α, N^ca-di-tert-butyloxycarbonylhomoglutamine to synthesis of thyrotropin-releasing hormone (TRH) analogs was examined. The δ-lactam formation from homoglutaminylpeptides took place more easily than γ-lactam formation from glutaminylpeptides in water or dioxane containing acetic acid. [pHgu¹, Nva²]-TRH had dose-dependent antagonistic activity against pentobarbital anesthesia in mice, but almost no binding activity to TRH receptor in rat brain.

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