title: A novel type of luciferin from the Siberian luminous earthworm Fridericia heliota: structure elucidation by spectral studies and total synthesis.
abstract: The structure elucidation and synthesis of the luciferin from the recently discovered luminous earthworm Fridericia heliota is reported. This luciferin is a key component of a novel ATP-dependent bioluminescence system. UV, fluorescence, NMR, and HRMS spectroscopy studies were performed on 0.005 mg of the isolated substance and revealed four isomeric structures that conform to spectral data. These isomers were chemically synthesized and one of them was found to produce light when reacted with a protein extract from F. heliota. The novel luciferin was found to have an unusual extensively modified peptidic nature, thus implying an unprecedented mechanism of action.
authors.affiliation: Laboratory of Bioluminescent Biotechnologies, Institute of Fundamental Biology and Biotechnology, Siberian Federal University pr. Svobodnyi, 79, Krasnoyarsk 660041 (Russia); Laboratory of Photobiology, Institute of Biophysics, Siberian Branch of the Russian Academy of Sciences, Akademgorodok, Krasnoyarsk 660036 (Russia).
authors.forename: Valentin N
authors.initials: VN
authors.lastname: Petushkov
authors.forename: Maxim A
authors.initials: MA
authors.lastname: Dubinnyi
authors.forename: Aleksandra S
authors.initials: AS
authors.lastname: Tsarkova
authors.forename: Natalja S
authors.initials: NS
authors.lastname: Rodionova
authors.forename: Mikhail S
authors.initials: MS
authors.lastname: Baranov
authors.forename: Vadim S
authors.initials: VS
authors.lastname: Kublitski
authors.forename: Osamu
authors.initials: O
authors.lastname: Shimomura
authors.forename: Ilia V
authors.initials: IV
authors.lastname: Yampolsky
mesh_terms: D000255:Adenosine Triphosphate / Q000378:metabolism; D000818:Animals; D007536:Isomerism; D049408:Luminescent Agents / Q000138:chemical synthesis / Q000737:chemistry*; D008163:Luminescent Measurements; D009835:Oligochaeta / Q000378:metabolism*; D010455:Peptides / Q000737:chemistry; D012800:Siberia
chemical_list: D049408:Luminescent Agents; D010455:Peptides; D000255:Adenosine Triphosphate
keywords: NMR spectroscopy; bioluminescence; luciferin; natural products; total synthesis