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1.
ChemSusChem ; 13(11): 2807-2827, 2020 Jun 08.
Artigo em Inglês | MEDLINE | ID: mdl-32180357

RESUMO

Lignin is the second most earth-abundant biopolymer having aromatic unit structures, but it has received less attention than other natural biomaterials. Recent advances in the development of lignin-based materials, such as mesoporous carbon, flexible thin films, and fiber matrix, have found their way into applications to photovoltaic devices, energy-storage systems, mechanical energy harvesters, and catalytic components. In this Review, we summarize and suggest another dimension of lignin valorization as a building block for the synthesis of functional materials in the fields of energy and environmental applications. We cover lignin-based materials in the photovoltaic and artificial photosynthesis for solar energy conversion applications. The most recent technological evolution in lignin-based triboelectric nanogenerators is summarized from its fundamental properties to practical implementations. Lignin-derived catalysts for solar-to-heat conversion and oxygen reduction are discussed. For energy-storage applications, we describe the utilization of lignin-based materials in lithium-ion rechargeable batteries and supercapacitors (e.g., electrodes, binders, and separators). We also summarize the use of lignin-based materials as heavy-metal adsorbents for environmental remediation. This Review paves the way to future potentials and opportunities of lignin as a renewable material for energy and environmental applications.


Assuntos
Recuperação e Remediação Ambiental , Lignina/química , Energia Renovável , Capacitância Elétrica , Resíduos
2.
Sci Adv ; 5(7): eaax0501, 2019 07.
Artigo em Inglês | MEDLINE | ID: mdl-31334353

RESUMO

Nicotinamide adenine dinucleotide (NAD+) is a key redox compound in all living cells responsible for energy transduction, genomic integrity, life-span extension, and neuromodulation. Here, we report a new function of NAD+ as a molecular photocatalyst in addition to the biological roles. Our spectroscopic and electrochemical analyses reveal light absorption and electronic properties of two π-conjugated systems of NAD+. Furthermore, NAD+ exhibits a robust photostability under UV-Vis-NIR irradiation. We demonstrate photocatalytic redox reactions driven by NAD+, such as O2 reduction, H2O oxidation, and the formation of metallic nanoparticles. Beyond the traditional role of NAD+ as a cofactor in redox biocatalysis, NAD+ executes direct photoactivation of oxidoreductases through the reduction of enzyme prosthetic groups. Consequently, the synergetic integration of biocatalysis and photocatalysis using NAD+ enables solar-to-chemical conversion with the highest-ever-recorded turnover frequency and total turnover number of 1263.4 hour-1 and 1692.3, respectively, for light-driven biocatalytic trans-hydrogenation.


Assuntos
Biocatálise , Luz , NAD/metabolismo , Elétrons , Hidrogenação , Íons , Metais/metabolismo , Oxirredução , Oxigênio/metabolismo , Água/metabolismo
3.
Nat Commun ; 9(1): 4208, 2018 10 11.
Artigo em Inglês | MEDLINE | ID: mdl-30310064

RESUMO

Redox enzymes catalyze fascinating chemical reactions with excellent regio- and stereo-specificity. Nicotinamide adenine dinucleotide cofactor is essential in numerous redox biocatalytic reactions and needs to be regenerated because it is consumed as an equivalent during the enzymatic turnover. Here we report on unbiased photoelectrochemical tandem assembly of a photoanode (FeOOH/BiVO4) and a perovskite photovoltaic to provide sufficient potential for cofactor-dependent biocatalytic reactions. We obtain a high faradaic efficiency of 96.2% and an initial conversion rate of 2.4 mM h-1 without an external applied bias for the photoelectrochemical enzymatic conversion of α-ketoglutarate to L-glutamate via L-glutamate dehydrogenase. In addition, we achieve a total turnover number and a turnover frequency of the enzyme of 108,800 and 6200 h-1, respectively, demonstrating that the tandem configuration facilitates redox biocatalysis using light as the only energy source.

4.
Small ; 14(40): e1801396, 2018 10.
Artigo em Inglês | MEDLINE | ID: mdl-30198161

RESUMO

Amyloidogenic peptides can self-assemble into highly ordered nanostructures consisting of cross ß-sheet-rich networks that exhibit unique physicochemical properties and high stability. Light-harvesting amyloid nanofibrils are constructed by employing insulin as a building block and thioflavin T (ThT) as a amyloid-specific photosensitizer. The ability of the self-assembled amyloid scaffold to accommodate and align ThT in high density on its surface allows for efficient energy transfer from the chromophores to the catalytic units in a similar way to natural photosystems. Insulin nanofibrils significantly enhance the photoactivity of ThT by inhibiting nonradiative conformational relaxation around the central CC bonds and narrowing the distance between ThT molecules that are bound to the ß-sheet-rich amyloid structure. It is demonstrated that the ThT-amyloid hybrid nanostructure is suitable for biocatalytic solar-to-chemical conversion by integrating the light-harvesting amyloid module (for nicotinamide cofactor regeneration) with a redox biocatalytic module (for enzymatic reduction).


Assuntos
Amiloide/química , Benzotiazóis/química , Nanoestruturas/química , Fotossíntese/fisiologia , Catálise
5.
Angew Chem Int Ed Engl ; 57(42): 13825-13828, 2018 10 15.
Artigo em Inglês | MEDLINE | ID: mdl-30062834

RESUMO

Light-driven activation of redox enzymes is an emerging route for sustainable chemical synthesis. Among redox enzymes, the family of Old Yellow Enzyme (OYE) dependent on the nicotinamide adenine dinucleotide cofactor (NADH) catalyzes the stereoselective reduction of α,ß-unsaturated hydrocarbons. Here, we report OYE-catalyzed asymmetric hydrogenation through light-driven regeneration of NADH and its analogues (mNADHs) by N-doped carbon nanodots (N-CDs), a zero-dimensional photocatalyst. Our spectroscopic and photoelectrochemical analyses verified the transfer of photo-induced electrons from N-CDs to an organometallic electron mediator (M) for highly regioselective regeneration of cofactors. Light triggered the reduction of NAD+ and mNAD+ s with the cooperation of N-CDs and M, and the reduction behaviors of cofactors were dependent on their own reduction peak potentials. The regenerated cofactors subsequently delivered hydrides to OYE for stereoselective conversions of a broad range of substrates with excellent biocatalytic efficiencies.


Assuntos
Biocatálise , Carbono/química , NAD/química , Nanoestruturas/química , Elétrons
6.
Angew Chem Int Ed Engl ; 57(27): 7958-7985, 2018 07 02.
Artigo em Inglês | MEDLINE | ID: mdl-29194901

RESUMO

Biocatalytic transformation has received increasing attention in the green synthesis of chemicals because of the diversity of enzymes, their high catalytic activities and specificities, and mild reaction conditions. The idea of solar energy utilization in chemical synthesis through the combination of photocatalysis and biocatalysis provides an opportunity to make the "green" process greener. Oxidoreductases catalyze redox transformation of substrates by exchanging electrons at the enzyme's active site, often with the aid of electron mediator(s) as a counterpart. Recent progress indicates that photoinduced electron transfer using organic (or inorganic) photosensitizers can activate a wide spectrum of redox enzymes to catalyze fuel-forming reactions (e.g., H2 evolution, CO2 reduction) and synthetically useful reductions (e.g., asymmetric reduction, oxygenation, hydroxylation, epoxidation, Baeyer-Villiger oxidation). This Review provides an overview of recent advances in light-driven activation of redox enzymes through direct or indirect transfer of photoinduced electrons.


Assuntos
Luz , Oxirredutases/metabolismo , Biocatálise , Sistema Enzimático do Citocromo P-450/química , Sistema Enzimático do Citocromo P-450/metabolismo , Elétrons , NAD/química , Nanoestruturas/química , Oxirredução , Oxirredutases/química , Fármacos Fotossensibilizantes/química , Complexo de Proteínas do Centro de Reação Fotossintética/química , Complexo de Proteínas do Centro de Reação Fotossintética/metabolismo
7.
Biomacromolecules ; 18(11): 3551-3556, 2017 Nov 13.
Artigo em Inglês | MEDLINE | ID: mdl-28825470

RESUMO

Peptide self-assembly is a facile route to the development of bioorganic hybrid materials that have sophisticated nanostructures toward diverse applications. Here, we report the synthesis of self-assembled peptide (Fmoc-diphenylalanine, Fmoc-FF)/graphitic carbon nitride (g-C3N4) hydrogels for light harvesting and biomimetic photosynthesis through noncovalent interactions between aromatic rings in Fmoc-FF nanofibers and tris-s-triazine in g-C3N4 nanosheets. According to our analysis, the photocurrent density of the Fmoc-FF/g-C3N4 hydrogel was 1.8× higher (0.82 µA cm-1) than that of the pristine g-C3N4. This is attributed to effective exfoliation of g-C3N4 nanosheets in the Fmoc-FF/g-C3N4 network, facilitating photoinduced electron transfers. The Fmoc-FF/g-C3N4 hydrogel reduced NAD+ to enzymatically active NADH under light illumination at a high rate of 0.130 mol g-1 h-1 and drove light-responsive redox biocatalysis. Moreover, the Fmoc-FF/g-C3N4 scaffold could well-encapsulate key photosynthetic components, such as electron mediators, cofactors, and enzymes, without noticeable leakage, while retaining their functions within the hydrogel. The prominent activity of the Fmoc-FF/g-C3N4 hydrogel for biomimetic photosynthesis resulted from the easy transfer of photoexcited electrons from electron donors to NAD+ via g-C3N4 and electron mediators as well as the hybridization of key photosynthetic components in a confined space of the nanofiber network.


Assuntos
Enzimas/química , Hidrogel de Polietilenoglicol-Dimetacrilato/química , Peptídeos/química , Fotossíntese , Catálise , Dipeptídeos/química , Enzimas/síntese química , Fluorenos/química , Grafite/química , Hidrogel de Polietilenoglicol-Dimetacrilato/síntese química , Nanofibras/química , Nanoestruturas/química , Nitrilas/química , Peptídeos/síntese química
8.
Angew Chem Int Ed Engl ; 56(30): 8681-8685, 2017 07 17.
Artigo em Inglês | MEDLINE | ID: mdl-28544039

RESUMO

Enoate reductases from the family of old yellow enzymes (OYEs) can catalyze stereoselective trans-hydrogenation of activated C=C bonds. Their application is limited by the necessity for a continuous supply of redox equivalents such as nicotinamide cofactors [NAD(P)H]. Visible light-driven activation of OYEs through NAD(P)H-free, direct transfer of photoexcited electrons from xanthene dyes to the prosthetic flavin moiety is reported. Spectroscopic and electrochemical analyses verified spontaneous association of rose bengal and its derivatives with OYEs. Illumination of a white light-emitting-diode triggered photoreduction of OYEs by xanthene dyes, which facilitated the enantioselective reduction of C=C bonds in the absence of NADH. The photoenzymatic conversion of 2-methylcyclohexenone resulted in enantiopure (ee>99 %) (R)-2-methylcyclohexanone with conversion yields as high as 80-90 %. The turnover frequency was significantly affected by the substitution of halogen atoms in xanthene dyes.

9.
ChemSusChem ; 9(13): 1559-64, 2016 07 07.
Artigo em Inglês | MEDLINE | ID: mdl-27198582

RESUMO

Human urine is considered as an alternative source of hydrogen and electricity owing to its abundance and high energy density. Here we show the utility of human urine as a chemical fuel for driving redox biocatalysis in a photoelectrochemical cell. Ni(OH)2 -modified α-Fe2 O3 is selected as a photoanode for the oxidation of urea in human urine and black silicon (bSi) is used as a photocathode material for nicotinamide cofactor (NADH: hydrogenated nicotinamide adenine dinucleotide) regeneration. The electrons extracted from human urine are used for the regeneration of NADH, an essential hydride mediator that is required for numerous redox biocatalytic reactions. The catalytic reactions at both the photoanode and the photocathode were significantly enhanced by light energy that lowered the overpotential and generated high currents in the full cell system.


Assuntos
Biocatálise , Luz , NAD/química , Processos Fotoquímicos , Urina/química , Eletroquímica , Humanos , NAD/metabolismo , Oxirredução
10.
Angew Chem Int Ed Engl ; 54(3): 969-73, 2015 Jan 12.
Artigo em Inglês | MEDLINE | ID: mdl-25430544

RESUMO

Cytochromes P450 can catalyze various regioselective and stereospecific oxidation reactions of non-functionalized hydrocarbons. Here, we have designed a novel light-driven platform for cofactor-free, whole-cell P450 photo-biocatalysis using eosin Y (EY) as a photosensitizer. EY can easily enter into the cytoplasm of Escherichia coli and bind specifically to the heme domain of P450. The catalytic turnover of P450 was mediated through the direct transfer of photoinduced electrons from the photosensitized EY to the P450 heme domain under visible light illumination. The photoactivation of the P450 catalytic cycle in the absence of cofactors and redox partners is successfully conducted using many bacterial P450s (variants of P450 BM3) and human P450s (CYPs 1A1, 1A2, 1B1, 2A6, 2E1, and 3A4) for the bioconversion of different substrates, including marketed drugs (simvastatin, lovastatin, and omeprazole) and a steroid (17ß-estradiol), to demonstrate the general applicability of the light-driven, cofactor-free system.


Assuntos
Sistema Enzimático do Citocromo P-450/metabolismo , Luz , Proteínas de Bactérias/química , Proteínas de Bactérias/metabolismo , Biocatálise , Sistema Enzimático do Citocromo P-450/química , Transporte de Elétrons , Escherichia coli/metabolismo , Estradiol/química , Estradiol/metabolismo , Fluoresceína/química , Fluoresceína/metabolismo , Heme/química , Heme/metabolismo , Humanos , Lovastatina/química , Lovastatina/metabolismo , Omeprazol/química , Omeprazol/metabolismo , Oxirredução , Fármacos Fotossensibilizantes/química , Fármacos Fotossensibilizantes/metabolismo , Estrutura Terciária de Proteína , Sinvastatina/química , Sinvastatina/metabolismo
11.
Bioconjug Chem ; 25(12): 2101-4, 2014 Dec 17.
Artigo em Inglês | MEDLINE | ID: mdl-25322062

RESUMO

We describe an efficienct chemical conversion platform with in situ immobilization of P450-BM3 on poly(3-hydroxybutyrate) granules. Through fusion with phasin, P450-BM3 is easily immobilized on poly(3-hydroxybutyrate) granules in Escherichia coli. In our work, the immobilized P450 exhibited higher stability and catalytic activity compared to free P450 against changes of pH, temperature, and concentrations of urea and ions. Through quick recovery of immobilized enzyme, the P450-P(3HB) complex successfully catalyzed an O-dealkylation reaction several times with maintained activity. Using the robust P450-P(3HB) complex, we performed a P450-catalyzed reaction on a preparative reactor scale (100 mL) and high-level production (12.3 µM) of 7-hydroxycoumarine from 7-ethoxycoumarin could be achieved.


Assuntos
Sistema Enzimático do Citocromo P-450/química , Sistema Enzimático do Citocromo P-450/metabolismo , Enzimas Imobilizadas/química , Hidroxibutiratos/química , Poliésteres/química , Proteínas de Bactérias/química , Proteínas de Bactérias/genética , Proteínas de Bactérias/metabolismo , Cumarínicos/metabolismo , Sistema Enzimático do Citocromo P-450/genética , Estabilidade Enzimática , Enzimas Imobilizadas/genética , Enzimas Imobilizadas/metabolismo , Escherichia coli , Concentração de Íons de Hidrogênio , NADPH-Ferri-Hemoproteína Redutase/química , NADPH-Ferri-Hemoproteína Redutase/genética , NADPH-Ferri-Hemoproteína Redutase/metabolismo , Proteínas Recombinantes/química , Proteínas Recombinantes/genética , Proteínas Recombinantes/metabolismo , Temperatura , Umbeliferonas/metabolismo , Ureia/química
12.
ChemSusChem ; 7(11): 3007-11, 2014 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-25204888

RESUMO

The photoelectroenzymatic synthesis of chemical compounds employing platinum nanoparticle-decorated silicon nanowires (Pt-SiNWs) is presented. The Pt-SiNWs proved to be an efficient material for photoelectrochemical cofactor regeneration because the silicon nanowires absorbs a wide range of the solar spectrum while the platinum nanoparticle serve as an excellent catalyst for electron and proton transfer. By integrating the platform with redox enzymatic reaction, visible-light-driven electroenzymatic synthesis of L-glutamate was achieved. Compared to electrochemical and photochemical methods, this approach is free from side reactions caused by sacrificial electron donors and has the advantage of applying low potential to realize energy-efficient and sustainable synthesis of chemicals by a photoelectroenzymatic system.


Assuntos
Nanopartículas Metálicas/química , NAD/química , Nanofios/química , Platina/química , Silício/química , Eletroquímica , Eletrodos , Ácido Glutâmico/química , Ácidos Cetoglutáricos/química , Luz , Nanofios/efeitos da radiação , Silício/efeitos da radiação
13.
Chemistry ; 20(38): 12020-5, 2014 Sep 15.
Artigo em Inglês | MEDLINE | ID: mdl-25088448

RESUMO

Efficient harvesting of unlimited solar energy and its conversion into valuable chemicals is one of the ultimate goals of scientists. With the ever-increasing concerns about sustainable growth and environmental issues, numerous efforts have been made to develop artificial photosynthetic process for the production of fuels and fine chemicals, thus mimicking natural photosynthesis. Despite the research progress made over the decades, the technology is still in its infancy because of the difficulties in kinetic coupling of whole photocatalytic cycles. Herein, we report a new type of artificial photosynthesis system that can avoid such problems by integrally coupling biocatalytic redox reactions with photocatalytic water splitting. We found that photocatalytic water splitting can be efficiently coupled with biocatalytic redox reactions by using tetracobalt polyoxometalate and Rh-based organometallic compound as hole and electron scavengers, respectively, for photoexcited [Ru(bpy)3](2+). Based on these results, we could successfully photosynthesize a model chiral compound (L-glutamate) using a model redox enzyme (glutamate dehydrogenase) upon in situ photoregeneration of cofactors.


Assuntos
Materiais Biomiméticos/química , Elétrons , Energia Solar , Água/química , Biocatálise , Transporte de Elétrons , Fotossíntese
14.
Chemistry ; 19(14): 4392-406, 2013 Apr 02.
Artigo em Inglês | MEDLINE | ID: mdl-23436280

RESUMO

In green plants, solar-energy utilization is accomplished through a cascade of photoinduced electron transfer, which remains a target model for realizing artificial photosynthesis. We introduce the concept of biocatalyzed artificial photosynthesis through coupling redox biocatalysis with photocatalysis to mimic natural photosynthesis based on visible-light-driven regeneration of enzyme cofactors. Key design principles for reaction components, such as electron donors, photosensitizers, and electron mediators, are described for artificial photosynthesis involving biocatalytic assemblies. Recent research outcomes that serve as a proof of the concept are summarized and current issues are discussed to provide a future perspective.


Assuntos
Fotossíntese , Biocatálise , Transporte de Elétrons , Luz , Oxirredução , Fármacos Fotossensibilizantes , Energia Solar , Luz Solar , Xantenos/química
15.
Biotechnol Bioeng ; 110(2): 383-90, 2013 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-23007262

RESUMO

Cytochrome P450 monooxygenases are multifunctional enzymes with potential applications in chemoenzymatic synthesis of complex chemicals as well as in studies of metabolism and xenobiotics. Widespread application of cytochrome P450s, however, is encumbered by the critical need for redox equivalents in their catalytic function. To overcome this limitation, we studied visible light-driven regeneration of NADPH for P450-catalyzed O-dealkylation reaction; we used eosin Y as a photosensitizing dye, triethanolamine as an electron donor, and [Cp*Rh(bpy)H2O] as an electron mediator. We analyzed catalytic activity of cell-free synthesized P450 BM3 monooxygenase variant (Y51F/F87A, BM3m2) in the presence of key components for NADPH photoregeneration. The P450-catalyzed O-dealkylation reaction sustainably maintained its turnover with the continuous supply of photoregenerated NADPH. Visible light-driven, non-enzymatic NADPH regeneration provides a new route for efficient, sustainable utilization of P450 monooxygenases.


Assuntos
Biotecnologia/métodos , Sistema Enzimático do Citocromo P-450/metabolismo , NADP/metabolismo , Sistema Livre de Células , Remoção de Radical Alquila , Amarelo de Eosina-(YS)/química , Luz , Redes e Vias Metabólicas , NADP/análise , Oxirredução , Fotobiorreatores , Processos Fotoquímicos
17.
Biomaterials ; 33(26): 6098-104, 2012 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-22681977

RESUMO

The interactions between cells and materials play critical roles in the success of new scaffolds for tissue engineering, since chemical and physical properties of biomaterials regulate cell adhesion, proliferation, migration, and differentiation. We have developed nanofibrous substrates that possess both topographical cues and electroactivity. The nanofiber scaffolds were fabricated through the electrospinning of polycaprolactone (PCL, a biodegradable polymer) and polyaniline (PANi, a conducting polymer) blends. We investigated the ways in which those properties influenced myoblast behaviors. Neither nanofiber alignment nor PANi concentration influenced cell growth and proliferation, but cell morphology changed significantly from multipolar to bipolar with the anisotropy of nanofibers. According to our analyses of myosin heavy chain expression, multinucleate myotube formation, and the expression of differentiation-specific genes (myogenin, troponin T, MHC), the differentiation of myoblasts on PCL/PANi nanofibers was strongly dependent on both nanofiber alignment and PANi concentration. Our results suggest that topographical cues and the electroactivity of nanofibers synergistically stimulate muscle cell differentiation to make PCL/PANi nanofibers a suitable scaffold material for skeletal tissue engineering.


Assuntos
Mioblastos/citologia , Nanofibras/química , Engenharia Tecidual/métodos , Animais , Diferenciação Celular/efeitos dos fármacos , Linhagem Celular , Imuno-Histoquímica , Camundongos , Microscopia Eletrônica de Varredura , Fibras Musculares Esqueléticas/citologia , Fibras Musculares Esqueléticas/metabolismo , Poliésteres/química , Polímeros/química , Polímeros/farmacologia , Reação em Cadeia da Polimerase em Tempo Real , Alicerces Teciduais/química
18.
Chemistry ; 18(18): 5490-5, 2012 Apr 27.
Artigo em Inglês | MEDLINE | ID: mdl-22488767

RESUMO

NAD analogues can be employed as artificial electron carriers for photoenzymatic synthesis under visible light. Four different NAD analogues that have a 3-substituted pyridine ring have been investigated. 3-Acetylpyridine adenine dinucleotide and 3-pyridinealdehyde adenine dinucleotide were photochemically reduced much more efficiently than NAD, while their reduced products showed coenzyme activity comparable to natural NAD.


Assuntos
Elétrons , NAD/análogos & derivados , Coenzimas/química , Coenzimas/metabolismo , Luz , NAD/química , NAD/metabolismo , Oxirredução
19.
Nanotechnology ; 22(49): 494020, 2011 Dec 09.
Artigo em Inglês | MEDLINE | ID: mdl-22101139

RESUMO

A strategy for the on-surface synthesis of silver nanoparticles (AgNPs) on a variety of two- to three-dimensional material surfaces, utilizing polydopamine, an emerging surface modifying agent, is reported in this paper. This material-independent platform for AgNP synthesis is useful for fabricating organic/inorganic hybrid nanomaterials and for preparing substrates for laser desorption-ionization time-of-flight mass spectrometry (LDI-ToF MS).


Assuntos
Indóis/química , Nanopartículas/química , Nanoestruturas/química , Nanotecnologia/métodos , Polímeros/química , Prata/química , Espectrometria de Massas por Ionização e Dessorção a Laser Assistida por Matriz , Nanopartículas/ultraestrutura , Nanoestruturas/ultraestrutura , Peptídeos/análise , Espectrometria de Massas por Ionização e Dessorção a Laser Assistida por Matriz/métodos , Propriedades de Superfície
20.
Chem Commun (Camb) ; 47(46): 12538-40, 2011 Dec 14.
Artigo em Inglês | MEDLINE | ID: mdl-22003495

RESUMO

For the first time, employment of nicotinamide coenzyme NAD analogs has overcome the limitations of NAD in electrochemical regeneration. It has been shown that NAD analogs, APAD and PAAD, were electrochemically reduced more efficiently than original NAD and that the stability of their reduced products was also much higher than NADH.


Assuntos
Eletroquímica/métodos , NAD/análogos & derivados , Catálise , NAD/química , Compostos Organometálicos/química , Oxirredução
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