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Novel Mechanism of Bioluminescence: Oxidative Decarboxylation of a Moiety Adjacent to the Light Emitter of Fridericia Luciferin [Text] / M. A. Dubinnyi [et al.] // Angew. Chem.-Int. Edit. - 2015. - Vol. 54, Is. 24. - P7065-7067, DOI 10.1002/anie.201501668. - Cited References:15. - We thank Dr. K.V. Antonov for acquisition of LC-HRMS spectra and Prof. Gary Schuster for fruitful discussion. This work was supported by the Russian Science Foundation grant 14-50-00131. M.S.B. acknowledges support by a stipend program of the President of the Russian Federation. K.M.S. acknowledges generous support from the National Science Foundation (CHE-1213047). This research was carried out using the equipment provided by IBCH core facility (CKP IBCH). . - ISSN 1433-7851. - ISSN 1521-3773

РУБ Chemistry, Multidisciplinary
Рубрики:
STRUCTURE ELUCIDATION
CHEMILUMINESCENCE
CYPRIDINA
Кл.слова (ненормированные):
bioluminescence -- bioorganic chemistry -- luciferin -- oxidative -- decarboxylation -- peptides
Аннотация: A novel luciferin from a bioluminescent Siberian earthworm Fridericia heliota was recently described. In this study, the Fridericia oxyluciferin was isolated and its structure elucidated. The results provide insight into a novel bioluminescence mechanism in nature. Oxidative decarboxylation of a lysine fragment of the luciferin supplies energy for light generation, while a fluorescent CompX moiety remains intact and serves as the light emitter.

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Держатели документа:
Russian Acad Sci, Inst Bioorgan Chem, Moscow 117997, Russia.
Pirogov Russian Natl Res Med Univ, Moscow 117997, Russia.
Russian Acad Sci, Akademgorodok, Siberian Branch, Lab Photobiol,Inst Biophys, Krasnoyarsk 660036, Russia.
Russian Acad Sci, Branch Shemyakin, Pushchino 142290, Russia.
Russian Acad Sci, Ovchinnikov Inst Bioorgan Chem, Pushchino 142290, Russia.

Доп.точки доступа:
Dubinnyi, Maxim A.; Kaskova, Zinaida M.; Rodionova, Natalja S.; Baranov, Mikhail S.; Gorokhovatsky, Andrey Yu.; Kotlobay, Alexey; Solntsev, Kyril M.; Tsarkova, Aleksandra S.; Petushkov, Valentin N.; Yampolsky, Ilia V.; Russian Science Foundation [14-50-00131]; President of the Russian Federation; National Science Foundation [CHE-1213047]

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Mechanism and color modulation of fungal bioluminescence / Z. M. Kaskova [et al.] // Sci. Adv. - 2017. - Vol. 3, Is. 4. - Ст. e1602847, DOI 10.1126/sciadv.1602847. - Cited References:40. - This work was supported by the Sao Paulo Research Foundation [FAPESP grants 10/11578-5 (to A.G.O.), 13/16885-1 (to C.V.S.), 14/14866-2 (to E.L.B.), 13/07914-8 (to E.P. and F.A.D.), and 2012/12663-1 (to P.D.M.) and CEPID Redoxoma 2013/07937-8 (to P.D.M.)], the National Council for Scientific and Technological Development (CNPq) [301307/2013-0 (to P.D.M.)], NAP Redoxoma (PRPUSP) [2011.1.9352.1.8. (to P.D.M.)], the Japan Society for the Promotion of Science Grants-in-Aid for Scientific Research (KAKENHI) [grant no. 16K07715 (to Y.O.)], Chubu University [grant AII28II M01 (to Y.O.)], and the Russian Science Foundation (grant 16-14-00052 to all Russian authors). . - ISSN 2375-2548

РУБ Multidisciplinary Sciences
Рубрики:
SINGLET MOLECULAR-OXYGEN
QUANTUM YIELDS
CHEMILUMINESCENCE
Аннотация: Bioluminescent fungi are spread throughout the globe, but details on their mechanism of light emission are still scarce. Usually, the process involves three key components: an oxidizable luciferin substrate, a luciferase enzyme, and a light emitter, typically oxidized luciferin, and called oxyluciferin. We report the structure of fungal oxyluciferin, investigate the mechanism of fungal bioluminescence, and describe theuseof simple synthetic alpha-pyrones as luciferins to produce multicolor enzymatic chemiluminescence. A high-energy endoperoxide is proposed as an intermediate of the oxidation of the native luciferin to the oxyluciferin, which is a pyruvic acid adduct of caffeic acid. Luciferase promiscuity allows the use of simple alpha-pyrones as chemiluminescent substrates.

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Держатели документа:
Russian Acad Sci, Inst Bioorgan Chem, Miklukho Maklaya 16-10, Moscow 117997, Russia.
Pirogov Russian Natl Res Med Univ, OStrovitianov 1, Moscow 117997, Russia.
SB RAS, Fed Res Ctr Krasnoyarsk Sci Ctr, Inst Biophys, Krasnoyarsk 660036, Russia.
Univ Sao Paulo, Fac Ciencias Farmaceut, Dept Anal Clin & Toxicolgicas, BR-05508900 Sao Paulo, Brazil.
Nagoya Univ, Grad Sch Bioagr Sci, Nagoya, Aichi 4648601, Japan.
Univ Sao Paulo, Inst Quim, Dept Bioquim, BR-05508900 Sao Paulo, Brazil.
Univ Sao Paulo, Inst Quim, Dept Quim Fundamental, BR-05508900 Sao Paulo, Brazil.
Univ Sao Paulo, Inst Oceanografico, Dept Oceanografia Fis Quim & Geol, BR-05508120 Sao Paulo, Brazil.
Chubu Univ, Dept Environm Biol, Kasugai, Aichi 4878501, Japan.

Доп.точки доступа:
Kaskova, Zinaida M.; Dorr, Felipe A.; Petushkov, Valentin N.; Purtov, Konstantin V.; Tsarkova, Aleksandra S.; Rodionova, Natalja S.; Mineev, Konstantin S.; Guglya, Elena B.; Kotlobay, Alexey; Baleeva, Nadezhda S.; Baranov, Mikhail S.; Arseniev, Alexander S.; Gitelson, Josef I.; Lukyanov, Sergey; Suzuki, Yoshiki; Kanie, Shusei; Pinto, Ernani; Di Mascio, Paolo; Waldenmaier, Hans E.; Pereira, Tatiana A.; Carvalho, Rodrigo P.; Oliveira, Anderson G.; Oba, Yuichi; Bastos, Erick L.; Stevani, Cassius V.; Yampolsky, Ilia V.; Sao Paulo Research Foundation [FAPESP] [10/11578-5, 13/16885-1, 14/14866-2, 13/07914-8, 2012/12663-1]; CEPID Redoxoma [2013/07937-8]; National Council for Scientific and Technological Development (CNPq) [301307/2013-0]; NAP Redoxoma (PRPUSP) [2011.1.9352.1.8]; Japan Society for the Promotion of Science [16K07715]; Chubu University [AII28II M01]; Russian Science Foundation [16-14-00052]

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577.34
С 87


    Структура оксилюциферина грибов - продукта реакции биолюминесценции [Текст] : статья / К. В. Пуртов [и др.] // Доклады Академии наук. - 2017. - Т. 477, № 2. - С. 245-248, DOI 10.7868/S0869565217320226 . - ISSN 0869-5652
   Перевод заглавия: Structure of Fungal Oxyluciferin, the Product of the Bioluminescence Reaction

УДК

577.34

Аннотация: Определили структуру оксилюциферина грибов, провели ферментативную реакцию биолюминесценции в условиях насыщения по субстрату с дискретным мониторингом образующихся продуктов и установили структуры конечных продуктов реакции. На основе этих исследований разработали схему деградации оксилюциферина до конечных продуктов. Структуру оксилюциферина грибов подтвердили встречным синтезом.

РИНЦ,
РИНЦ
Держатели документа:
Федеральный исследовательский центр "Красноярский научный центр" Сибирского отделения Российской Академии наук

Доп.точки доступа:
Пуртов, К.В.; Purtov K.V.; Осипова, З.М.; Osipova Z.M.; Петушков, В.Н.; Petushkov V.N.; Родионова, Н.С.; Rodionova N.S.; Царькова, А.С.; Tsarkova A.S.; Котлобай, А.А.; Kotlobai A.A.; Чепурных, Т.В.; Chepurnykh T.V.; Гороховатский, А.Ю.; Gorokhovatsky A. Yu.; Ямпольский, И.В.; Yampolsky I.V.; Гительзон, И.И.; Gitelson J.I.

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Bioluminescence chemistry of fireworm Odontosyllis / A. A. Kotlobay [et al.] // Proc. Natl. Acad. Sci. U. S. A. - 2019. - Vol. 116, Is. 38. - P18911-18916, DOI 10.1073/pnas.1902095116. - Cited References:16. - We thank the late Dr. Shoji Inoue and Dr. Hisae Kakoi (Meijo University) for providing Odontosyllis materials, Sergey Shakhov for photography, and Drs. Mikhail Baranov and Andrey Mikhaylov for discussions. Some experiments were carried out using equipment provided by the Institute of Bioorganic Chemistry of the Russian Academy of Sciences.ore Facility. Some experiments were supported by Planta LLC. Structural and mechanistic studies were supported by Russian Science Foundation Grant 18-74-10102. Isolation, purification, and biochemical studies were supported by Russian Science Foundation Grant 16-14-00052p. B.R.B. acknowledges support from the Air Force Office of Scientific Research (FA9550-18-1-0017). . - ISSN 0027-8424

РУБ Multidisciplinary Sciences
Рубрики:
MECHANISM
DECARBOXYLATION
OXIDATION
Кл.слова (ненормированные):
bioluminescence -- Odontosyllis luciferin -- oxyluciferin -- heterocycles
Аннотация: Marine polychaetes Odontosyllis undecimdonta, commonly known as fireworms, emit bright blue-green bioluminescence. Until the recent identification of the Odontosyllis luciferase enzyme, little progress had been made toward characterizing the key components of this bioluminescence system. Here we present the biomolecular mechanisms of enzymatic (leading to light emission) and nonenzymatic (dark) oxidation pathways of newly described O. undecimdonta luciferin. Spectral studies, including 1D and 2D NMR spectroscopy, mass spectrometry, and X-ray diffraction, of isolated substances allowed us to characterize the luciferin as an unusual tricyclic sulfur-containing heterocycle. Odontosyllis luciferin does not share structural similarity with any other known luciferins. The structures of the Odontosyllis bioluminescent system's low molecular weight components have enabled us to propose chemical transformation pathways for the enzymatic and nonspecific oxidation of luciferin.

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Scopus
Держатели документа:
Russian Acad Sci, Shemyakin Ovchinnikov Inst Bioorgan Chem, Moscow 117997, Russia.
Moscow Inst Phys & Technol, Dolgoprudnyi 141701, Russia.
Russian Acad Sci, Siberian Branch, Krasnoyarsk Sci Ctr, Inst Biophys, Krasnoyarsk 660036, Russia.
Pirogov Russian Natl Res Med Univ, Moscow 117997, Russia.
Russian Acad Sci, AN Nesmeyanov Inst Organoelement Cpds, Moscow 119991, Russia.
Natl Res Ctr, Kurchatov Inst, Moscow 123182, Russia.
St Petersburg Natl Res Acad Univ, Russian Acad Sci, St Petersburg 194021, Russia.
Connecticut Coll, New London, CT 06320 USA.
European Mol Biol Lab Hamburg, D-22603 Hamburg, Germany.
Chubu Univ, Dept Environm Biol, Kasugai, Aichi 4878501, Japan.

Доп.точки доступа:
Kotlobay, Alexey A.; Dubinnyi, Maxim A.; Purtov, Konstantin V.; Guglya, Elena B.; Rodionova, Natalja S.; Petushkov, Valentin N.; Bolt, Yaroslav V.; Kublitski, Vadim S.; Kaskova, Zinaida M.; Ziganshin, Rustam H.; Nelyubina, Yulia V.; Dorovatovskii, Pavel V.; Eliseev, Igor E.; Branchini, Bruce R.; Bourenkov, Gleb; Ivanov, Igor A.; Oba, Yuichi; Yampolsky, Ilia V.; Tsarkova, Aleksandra S.; Kaskova, Zinaida; Russian Science FoundationRussian Science Foundation (RSF) [18-74-10102, 16-14-00052p]; Air Force Office of Scientific ResearchUnited States Department of DefenseAir Force Office of Scientific Research (AFOSR) [FA9550-18-1-0017]

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