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Каталог книг и продолжающихся изданий библиотеки Института биофизики СО РАН (1)

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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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A novel ATP-dependent bioluminescent system from the Siberian earthworm Fridericia heliota: structure elucidation of luciferin and its analogs [Text] / V. . Petushkov [et al.] // Luminescence. - 2014. - Vol. 29. - P54-55. - Cited References: 3 . - ISSN 1522-7235. - ISSN 1522-7243

WOS
Держатели документа:
[Dubinnyi, Maxim
Tsarkova, Aleksandra
Baranov, Mikhail
Yampolsky, Ilia] Russian Acad Sci, Inst Bioorgan Chem, Moscow, Russia
[Petushkov, Valentin
Rodionova, Natalja
Shimomura, Osamu] Russian Acad Sci, Inst Biophys, Lab Photobiol, Siberian Branch, Krasnoyarsk, Russia
ИБФ СО РАН : 660036, Красноярск, Академгородок, д. 50, стр. 50

Доп.точки доступа:
Petushkov, V...; Dubinnyi, M...; Tsarkova, A...; Rodionova, N...; Baranov, M...; Shimomura, O...; Yampolsky, I...

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A Novel Type of Luciferin from the Siberian Luminous Earthworm Fridericia heliota: Structure Elucidation by Spectral Studies and Total Synthesis [Text] / V. N. Petushkov [et al.] // Angew. Chem.-Int. Edit. - 2014. - Vol. 53, Is. 22. - P5566-5568, DOI 10.1002/anie.201400529. - Cited References: 13. - We thank Dr. Alexander O. Chizhov for recording mass spectra and Dr. K. S. Mineev for NMR analysis of synthetic intermediates. We acknowledge support from the Program of the Government of the Russian Federation "Measures to attract leading scientists to Russian educational institutions" (grant no. 11. G34.31.0058), the programs MCB RAS, President of the Russian Federation "Leading science school" (grant 3951.2012.4) and the Russian Foundation for Basic Research (grant 14-03-01015). B. M. S. was supported by a stipend from the Program of the President of the Russian Federation. . - ISSN 1433-7851. - ISSN 1521-3773

РУБ Chemistry, Multidisciplinary
Рубрики:
BIOLUMINESCENT EARTHWORM
Кл.слова (ненормированные):
bioluminescence -- luciferin -- natural products -- NMR spectroscopy -- total synthesis
Аннотация: 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.

WOS
Держатели документа:
[Petushkov, Valentin N.
Rodionova, Natalja S.
Shimomura, Osamu] Siberian Fed Univ, Inst Fundamental Biol & Biotechnol, Lab Bioluminescent Biotechnol, Krasnoyarsk 660041, Russia
[Petushkov, Valentin N.
Rodionova, Natalja S.] Russian Acad Sci, Siberian Branch, Inst Biophys, Lab Photobiol, Krasnoyarsk 660036, Russia
[Dubinnyi, Maxim A.
Tsarkova, Aleksandra S.
Baranov, Mikhail S.
Kublitski, Vadim S.
Yampolsky, Ilia V.] Russian Acad Sci, Inst Bioorgan Chem, Moscow 117997, Russia
[Shimomura, Osamu] Marine Biol Lab, Woods Hole, MA 02543 USA
ИБФ СО РАН : 660036, Красноярск, Академгородок, д. 50, стр. 50

Доп.точки доступа:
Petushkov, V.N.; Dubinnyi, M.A.; Tsarkova, A.S.; Rodionova, N.S.; Baranov, M.S.; Kublitski, V.S.; Shimomura, O...; Yampolsky, I.V.; 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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Novel Peptide Chemistry in Terrestrial Animals: Natural Luciferin Analogues from the Bioluminescent Earthworm Fridericia heliota [Text] / M. A. Dubinnyi [et al.] // Chem.-Eur. J. - 2015. - Vol. 21, Is. 10. - P3942-3947, DOI 10.1002/chem.201406498. - Cited References:17. - We thank Dr. K. V. Antonov for registration of LC-HRMS spectra. This work was supported by the Russian Science Foundation grant 14-50-00131. . - ISSN 0947-6539. - ISSN 1521-3765

РУБ Chemistry, Multidisciplinary
Рубрики:
STRUCTURE ELUCIDATION
DERIVATIVES
IDENTIFICATION
Кл.слова (ненормированные):
bioluminescence -- Fridericia heliota -- luciferin -- peptides -- structure -- elucidation
Аннотация: We report isolation and structure elucidation of AsLn5, AsLn7, AsLn11 and AsLn12: novel luciferin analogs from the bioluminescent earthworm Fridericia heliota. They were found to be highly unusual modified peptides, comprising either of the two tyrosine-derived chromophores, CompX or CompY and a set of amino acids, including threonine, gamma-aminobutyric acid, homoarginine, and unsymmetrical N,N-dimethylarginine. These natural compounds represent a unique peptide chemistry found in terrestrial animals and rise novel questions concerning their biosynthetic origin.

WOS,
Scopus
Держатели документа:
Institute of Bioorganic Chemistry, Russian Academy of Sciences, Miklukho-Maklaya 16/10, Moscow, Russian Federation
Pirogov Russian National Research Medical University, Ostrovitianov 1, Moscow, Russian Federation
Laboratory of Photobiology, Institute of Biophysics, Siberian Branch of the Russian Academy of Sciences, Akademgorodok, Krasnoyarsk, Russian Federation

Доп.точки доступа:
Dubinnyi, Maxim A.; Tsarkova, Aleksandra S.; Petushkov, Valentin N.; Kaskova, Zinaida M.; Rodionova, Natalja S.; Kovalchuk, Sergey I.; Ziganshin, Rustam H.; Baranov, Mikhail S.; Mineev, Konstantin S.; Yampolsky, Ilia V.; Russian Science Foundation [14-50-00131]

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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.

WOS
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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alpha-C-Mannosyltryptophan is a Structural Analog of the Luciferin from Bioluminescent Siberian Earthworm Henlea sp. / M. A. Dubinnyi, I. A. Ivanov, N. S. Rodionova [et al.] // ChemistrySelect. - 2020. - Vol. 5, Is. 42. - P13155-13159, DOI 10.1002/slct.202003075. - Cited References:49. - This work was supported by the State Assignment for Basic Research of the Russian Academy of Sciences (project no. 0356-2019-0019) and the Russian Foundation for Basic Research (project no. 19-04-00348-a). . - ISSN 2365-6549

РУБ Chemistry, Multidisciplinary
Рубрики:
STRUCTURE ELUCIDATION
   MANNOSYLATION
   TRYPTOPHAN
   PROTEIN
   COMPLEMENT
Кл.слова (ненормированные):
Bioluminescence -- Earthworm -- Henlea -- Natural products -- NMR spectroscopy
Аннотация: Cold extract from bioluminescent earthworm Henlea sp. was studied by HPLC, 1D and 2D NMR and LC-HRMS analysis. An abundant structural analog of the luciferin was isolated and identified as alpha-C-mannosyltryptophan (ManTrp), the product of unusual C2-glycosylation found earlier in humans, ascidians and other animals. Two compounds in cold extract (P300b, P300c) were characterized as C2-substituted derivatives of tryptophan. We hypothesize that a series of tryptophan-containing compounds are possible participants of bioluminescence-related metabolism in Henlea sp.

WOS
Держатели документа:
Russian Acad Sci, Shemyakin Ovchinnikov Inst Bioorgan Chem, GSP-7,Miklukho Maklaya Str 16-10, Moscow 117997, Russia.
Russian Acad Sci, Siberian Branch, Krasnoyarsk Res Ctr, Inst Biophys, Krasnoyarsk 660036, Russia.
Pirogov Russian Natl Res Med Univ, 1 Ostrovityanova St, Moscow 117997, Russia.

Доп.точки доступа:
Dubinnyi, Maxim A.; Ivanov, Igor A.; Rodionova, Natalia S.; Kovalchuk, Sergey I.; Kaskova, Zinaida M.; Petushkov, Valentin N.; State Assignment for Basic Research of the Russian Academy of Sciences [0356-2019-0019]; Russian Foundation for Basic ResearchRussian Foundation for Basic Research (RFBR) [19-04-00348-a]

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