title: Concise Synthesis of v-Coelenterazines.
abstract: A novel synthetic method for v-coelenterazine (v-CTZ), which is a vinylene-bridged analog of native CTZ with a large red-shifted luminescence property, is described. The synthesis was achieved in a concise way through the use of three sequential cross-coupling reactions and ring-closing metathesis (RCM). A newly synthesized C2-modified trifluoromethyl analog cf3-v-CTZ showed slightly more red-shifted luminescence than v-CTZ when it was used as a substrate for Renilla luciferases.
authors.affiliation: †Laboratory of Chemical Bioscience, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University, 2-3-10 Kanda-Surugadai, Chiyoda-ku, Tokyo 101-0062, Japan.
authors.forename: Takamitsu
authors.initials: T
authors.lastname: Hosoya
authors.affiliation: ‡Department of Biological Information, Graduate School of Bioscience and Biotechnology, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama 226-8501, Japan.
authors.forename: Rie
authors.initials: R
authors.lastname: Iimori
authors.affiliation: †Laboratory of Chemical Bioscience, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University, 2-3-10 Kanda-Surugadai, Chiyoda-ku, Tokyo 101-0062, Japan.
authors.forename: Suguru
authors.initials: S
authors.lastname: Yoshida
authors.affiliation: †Laboratory of Chemical Bioscience, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University, 2-3-10 Kanda-Surugadai, Chiyoda-ku, Tokyo 101-0062, Japan.
authors.forename: Yuto
authors.initials: Y
authors.lastname: Sumida
authors.affiliation: §Yokohama Research Center, JNC Co., 5-1 Okawa, Kanazawa-ku, Yokohama 236-8605, Japan.
authors.forename: Yuiko
authors.initials: Y
authors.lastname: Sahara-Miura
authors.affiliation: §Yokohama Research Center, JNC Co., 5-1 Okawa, Kanazawa-ku, Yokohama 236-8605, Japan.
authors.forename: Jun-ichi
authors.initials: J
authors.lastname: Sato
authors.affiliation: §Yokohama Research Center, JNC Co., 5-1 Okawa, Kanazawa-ku, Yokohama 236-8605, Japan.
authors.forename: Satoshi
authors.initials: S
authors.lastname: Inouye
mesh_terms: D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D049449:Luminescence; D049408:Luminescent Agents / Q000138:chemical synthesis* / Q000737:chemistry; D008386:Marine Biology; D015394:Molecular Structure; D011719:Pyrazines / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D007093:Imidazoles; D049408:Luminescent Agents; D011719:Pyrazines; C017144:coelenterazine