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1.


   
    LC-MS and microscale NMR analysis of luciferin-related compounds from the bioluminescent earthworm Fridericia heliota / S. M. Marques [et al.] // Journal of Photochemistry and Photobiology B: Biology. - 2011. - Vol. 102, Is. 3. - P218-223, DOI 10.1016/j.jphotobiol.2010.12.006 . - ISSN 1011-1344
Кл.слова (ненормированные):
Bioluminescence -- Earthworm -- Fridericia heliota -- Luciferin -- Microscale NMR -- RP-HPLC-MS -- alkene -- alkyl group -- benzothiazole -- carboxylic acid -- hydroxyl group -- luciferin -- pterin -- absorption -- article -- bioluminescence -- earthworm -- Fridericia heliota -- isomer -- molecular weight -- nonhuman -- nuclear magnetic resonance -- priority journal -- reversed phase high performance liquid chromatography -- ultraviolet radiation -- Animals -- Chromatography, High Pressure Liquid -- Chromatography, Reverse-Phase -- Firefly Luciferin -- Luminescent Agents -- Magnetic Resonance Spectroscopy -- Mass Spectrometry -- Oligochaeta -- Fridericia heliota
Аннотация: This paper presents the main results of RP-HPLC-MS and microscale NMR analysis performed on Accompanying similar to Luciferin (AsLn(x)), compounds present in extracts of the bioluminescent earthworm Fridericia heliota that display similarities with Fridericia's luciferin, the substrate of the bioluminescent reaction. Three isomers of AsLn were discovered, AsLn(1), AsLn(2) and AsLn(3), all of which present a molecular weight of 529 Da. Their UV-Vis absorption spectra show maxima at 235 nm for AsLn(1), 238 and 295 nm for AsLn(2) and 241 and 295 nm for AsLn(3). MS n fragmentation patterns suggest the existence of carboxylic acid and hydroxyl moieties, and possibly chemical groups found in other luciferins like pterin or benzothiazole. The major isomer, AsLn(2), presents an aromatic ring and alkene and alkyl moieties. These luciferin-like compounds can be used as models that could give further insights into the structure of this newly discovered luciferin. В© 2010 Elsevier Inc. All rights reserved.

Scopus
Держатели документа:
Department of Chemistry and Biochemistry, Faculty of Sciences, Universidade Do Porto, Rua do Campo Alegre 687, 4169-007 Porto, Portugal
Laboratory of Photobiology, Institute of Biophysics, Russian Academy of Sciences, Akademgorodok, 660036 Krasnoyarsk, Russian Federation : 660036, Красноярск, Академгородок, д. 50, стр. 50

Доп.точки доступа:
Marques, S.M.; Petushkov, V.N.; Rodionova, N.S.; Esteves Da Silva, J.C.G.

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2.


   
    CompX, a luciferin-related tyrosine derivative from the bioluminescent earthworm Fridericia heliota. Structure elucidation and total synthesis / V. N. Petushkov [et al.] // Tetrahedron Letters. - 2014. - Vol. 55, Is. 2. - P460-462, DOI 10.1016/j.tetlet.2013.11.064 . - ISSN 0040-4039
Кл.слова (ненормированные):
Bioluminescence -- Enchytraeid -- Luciferin -- Total synthesis
Аннотация: 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. © 2013 Elsevier Ltd. All rights reserved.

Scopus
Держатели документа:
Laboratory of Bioluminescent Biotechnologies, Institute of Fundamental Biology and Biotechnology, Siberian Federal University, pr. Svobodnyi, 79, Krasnoyarsk 660041, Russian Federation
Laboratory of Photobiology, Institute of Biophysics, Russian Academy of Sciences, Akademgorodok, Krasnoyarsk 660036, Russian Federation
Institute of Bioorganic Chemistry, Russian Academy of Sciences, Miklukho-Maklaya 16/10, Moscow 117997, Russian Federation
Department of Chemistry and Biochemistry, Faculty of Sciences, University of Porto, Campo Alegre St. 687, Porto 4169-007, Portugal
ИБФ СО РАН : 660036, Красноярск, Академгородок, д. 50, стр. 50

Доп.точки доступа:
Petushkov, V.N.; Tsarkova, A.S.; Dubinnyi, M.A.; Rodionova, N.S.; Marques, S.M.; Esteves Da Silva, J.C.G.; Shimomura, O.; Yampolsky, I.V.

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