CompX,a luciferin-related tyrosine derivative from the bioluminescent earthworm Fridericia heliota. Structure elucidation and total synthesis |
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| Authors: | Valentin N Petushkov Aleksandra S Tsarkova Maxim A Dubinnyi Natalja S Rodionova Simone M Marques Joaquim CG Esteves da Silva Osamu Shimomura Ilia V Yampolsky |
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| Institution: | 1. Laboratory of Bioluminescent Biotechnologies, Institute of Fundamental Biology and Biotechnology, Siberian Federal University, pr. Svobodnyi, 79, Krasnoyarsk 660041, Russia;2. Laboratory of Photobiology, Institute of Biophysics, Siberian Branch of the Russian Academy of Sciences, Akademgorodok, Krasnoyarsk 660036, Russia;3. Institute of Bioorganic Chemistry, Russian Academy of Sciences, Miklukho-Maklaya 16/10, Moscow 117997, Russia;4. Chemistry Research Center of the University of Porto (CIQ-UP), Department of Chemistry and Biochemistry, Faculty of Sciences, University of Porto, Campo Alegre St. 687, Porto 4169-007, Portugal |
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| Abstract: | A luciferin analog, CompX, was isolated from the extracts of the bioluminescent earthworm Fridericia heliota. Its structure was determined as (Z)-5-(2-carboxy-2-methoxyvinyl)-2-hydroxybenzoic acid by spectroscopic data analysis and was confirmed by total synthesis. The (Z)-configuration of the double bond was established by comparing the ROESY spectra of CompX with those of its synthetic (E)-isomer. CompX represents a tyrosine analog, not previously found in natural sources, and is probably derived from tyrosine by deamination, O-methylation of the resulting alpha-keto acid, and carboxylation at the aromatic core. |
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| Keywords: | Bioluminescence Enchytraeid Luciferin Total synthesis |
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