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A Novel Type of Luciferin from the Siberian Luminous Earthworm Fridericia heliota : Structure Elucidation by Spectral Studies and Total Synthesis
Author(s) -
Petushkov Valentin N.,
Dubinnyi Maxim A.,
Tsarkova Aleksandra S.,
Rodionova Natalja S.,
Baranov Mikhail S.,
Kublitski Vadim S.,
Shimomura Osamu,
Yampolsky Ilia V.
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201400529
Subject(s) - luciferin , bioluminescence , chemistry , earthworm , stereochemistry , fluorescence spectroscopy , fluorescence , biochemistry , luciferase , biology , ecology , physics , transfection , gene , quantum mechanics
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.