Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 22, Pages 5566-5568Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201400529
Keywords
bioluminescence; luciferin; natural products; NMR spectroscopy; total synthesis
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Funding
- Government of the Russian Federation Measures to attract leading scientists to Russian educational institutions [11. G34.31.0058]
- programs MCB RAS
- Russian Federation Leading science school [3951.2012.4]
- Russian Foundation for Basic Research [14-03-01015]
- Russian Federation
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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.
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