title: Synthesis of thyrotropin-releasing hormone-related peptides using N alpha-tert-butyloxycarbonyl-omega-(N-tert-butyloxycarbonylcarbamoyl)- alpha-amino acids.
abstract: Application of N alpha,Nca-di-tert-butyloxycarbonylhomoglutamine to synthesis of thyrotropin-releasing hormone (TRH) analogs was examined. The delta-lactam formation from homoglutaminylpeptides took place more easily than gamma-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.
authors.forename: N
authors.initials: N
authors.lastname: Sakura
authors.forename: K
authors.initials: K
authors.lastname: Hirose
authors.forename: M
authors.initials: M
authors.lastname: Nishijima
authors.forename: T
authors.initials: T
authors.lastname: Hashimoto
authors.forename: T
authors.initials: T
authors.lastname: Okabe
authors.forename: C
authors.initials: C
authors.lastname: Miyamori
authors.forename: T
authors.initials: T
authors.lastname: Sato
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis*; D000818:Animals; D005561:Formates / Q000138:chemical synthesis*; D005563:Formic Acid Esters / Q000138:chemical synthesis*; D008297:Male; D051379:Mice; D008813:Mice, Inbred ICR; D009842:Oligopeptides / Q000138:chemical synthesis*; D010424:Pentobarbital / Q000494:pharmacology; D051381:Rats; D011989:Receptors, Thyrotropin / Q000187:drug effects / Q000378:metabolism; D012890:Sleep / Q000187:drug effects; D013973:Thyrotropin-Releasing Hormone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology
chemical_list: D000596:Amino Acids; D005561:Formates; D005563:Formic Acid Esters; D009842:Oligopeptides; D011989:Receptors, Thyrotropin; C000345:t-butyloxycarbonyl group; D013973:Thyrotropin-Releasing Hormone; D010424:Pentobarbital