title: 2-Diazohistidinyl thyrotropin-releasing hormone (TRH): a photosensitive TRH analog.
abstract: We have synthesized a new thyrotropin releasing hormone (TRH) analog, pGlu-2-diazo-His-Pro-NH2 5, which is a potential photoaffinity label for the TRH receptor. Its precursor, pGlu-2-amino-His-Pro-NH2 4, has been synthesized through successive coupling of a 2-aminohistidine derivative 1 with proline and pyroglutamic acid derivatives. Diazotization of the fully deprotected tripeptide 4 gave the photoactivatable TRH analog 5. Compounds 4 and 5 exhibit IC50 values of 2 and 8 microM respectively, to be compared to the 0.02 microM value for native TRH.
authors.affiliation: Merrell-Dow Research Institute, Strasbourg, France.
authors.forename: J P
authors.initials: JP
authors.lastname: Meyer
authors.forename: J T
authors.initials: JT
authors.lastname: Pelton
authors.forename: M
authors.initials: M
authors.lastname: Goeldner
authors.forename: C
authors.initials: C
authors.lastname: Hirth
mesh_terms: D000595:Amino Acid Sequence; D000818:Animals; D006624:Hippocampus / Q000378:metabolism; D008027:Light; D008297:Male; D008969:Molecular Sequence Data; D015394:Molecular Structure; D010777:Photochemistry; D011761:Pyrrolidonecarboxylic Acid / Q000031:analogs & derivatives; D051381:Rats; D011919:Rats, Inbred Strains; D017981:Receptors, Neurotransmitter / Q000378:metabolism; D018025:Receptors, Thyrotropin-Releasing Hormone; D013973:Thyrotropin-Releasing Hormone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000378:metabolism / Q000528:radiation effects
chemical_list: D017981:Receptors, Neurotransmitter; D018025:Receptors, Thyrotropin-Releasing Hormone; D013973:Thyrotropin-Releasing Hormone; C070429:thyrotropin-releasing hormone, 2-diazohistidinyl-; D011761:Pyrrolidonecarboxylic Acid