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Journal articles on the topic 'Oxygenation Reactions'

Author: Grafiati

Published: 18 May 2024

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1

Das, Ujjwal. "Platinum Group Metals Bonded Thiolato Sulfur Oxygenation: Photoactivity and Bioactivity." Asian Journal of Chemistry 34, no. 12 (2022): 3059–70. http://dx.doi.org/10.14233/ajchem.2022.24007.

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Platinum group metals mediated thiolato compounds are highly susceptible for S-centered reactivity owing to high nucleophilicity and which is enormously significant in the point of its bioactivity and photoactivity. A series of oxygenation reactions of thiolate sulfur attached with platinum metals occurred with molecular O2 in varying conditions. A variety of sulfenates and sulfinates are produced depending on nature of starting substrate thiolato and the oxygenations are facile under harshly oxygen environment. There are numerous mechanistic paths for the oxygenation of platinum metals bonded thiolate S-center unlike the oxygenation reaction of organic sulphides. It is assumed that S-oxygenation occurs via the intramolecular and intermolecular dioxygen addition pathways. A number of mysterious photo-induced sulphur oxygenation and self-sensitization reactions of metal-thiolato to analogous oxygenate are also mentioned. These compounds show enzymatic catalytic activity and remarkable bioactivity also interaction with the biomolecules like DNA, which opens a new area for the researchers for designing novel heavier metals-sulfur-oxygenates compounds as metallodrugs.

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2

Forchetta, Mattia, Francesca Valentini, Valeria Conte, Pierluca Galloni, and Federica Sabuzi. "Photocatalyzed Oxygenation Reactions with Organic Dyes: State of the Art and Future Perspectives." Catalysts 13, no. 2 (January 18, 2023): 220. http://dx.doi.org/10.3390/catal13020220.

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Oxygen atom incorporation into organic molecules is one of the most powerful strategies to increase their pharmacological activity and to obtain valuable intermediates in organic synthesis. Traditional oxidizing agents perform very well, but their environmental impact and their low selectivity constitute significant limitations. On the contrary, visible-light-promoted oxygenations represent a sustainable method for oxidizing organic compounds, since only molecular oxygen and a photocatalyst are required. Therefore, photocatalytic oxygenation reactions exhibit very high atom-economy and eco-compatibility. This mini-review collects and analyzes the most recent literature on organo-photocatalysis applications to promote the selective oxygenation of organic substrates. In particular, acridinium salts, Eosin Y, Rose Bengal, cyano-arenes, flavinium salts, and quinone-based dyes are widely used as photocatalysts in several organic transformations as the oxygenations of alkanes, alkenes, alkynes, aromatic compounds, amines, phosphines, silanes, and thioethers. In this context, organo-photocatalysts proved to be highly efficient in catalytic terms, showing similar or even superior performances with respect to their metal-based counterparts, while maintaining a low environmental impact. In addition, given the mild reaction conditions, visible-light-promoted photo-oxygenation processes often display remarkable selectivity, which is a striking feature for the late-stage functionalization of complex organic molecules.

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3

Bopp, Charlotte E., Hans-Peter E. Kohler, and Thomas B. Hofstetter. "Enzyme Kinetics of Organic Contaminant Oxygenations." CHIMIA International Journal for Chemistry 74, no. 3 (March 25, 2020): 108–14. http://dx.doi.org/10.2533/chimia.2020.108.

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Enzymatic oxygenations initiate biodegradation processes of many organic soil and water contaminants. Even though many biochemical aspects of oxygenation reactions are well-known, quantifying rates of oxidative contaminant removal as well as the extent of oxygenation remains a major challenge. Because enzymes use different strategies to activate O2, reactions leading to substrate oxygenation are not necessarily limiting the rate of contaminant removal. Moreover, oxygenases react along unproductive pathways without substrate metabolism leading to O2 uncoupling. Here, we identify the critical features of the catalytic cycles of selected oxygenases that determine rates and extents of biodegradation. We focus most specifically on Rieske dioxygenases, a subfamily of mononuclear non-heme ferrous iron oxygenases, because of their ability to hydroxylate unactivated aromatic structures and thus initiate the transformation of the most persistent organic contaminants. We illustrate that the rate-determining steps in their catalytic cycles range from O2 activation to substrate hydroxylation, depending on the extent of O–O cleavage that is required for generating the reactive Fe-oxygen species. The extent of O2 uncoupling, on the other hand, is highly substrate-specific and potentially modulated by adaptive responses to oxidative stress. Understanding the kinetic mechanisms of oxygenases will be key to assess organic contaminant biotransformation quantitatively.

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4

Yu, Mohan, and Yajun Liu. "A QM/MM Study on the Initiation Reaction of Firefly Bioluminescence—Enzymatic Oxidation of Luciferin." Molecules 26, no. 14 (July 12, 2021): 4222. http://dx.doi.org/10.3390/molecules26144222.

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Among all bioluminescent organisms, the firefly is the most famous, with a high luminescent efficiency of 41%, which is widely used in the fields of biotechnology, biomedicine and so on. The entire bioluminescence (BL) process involves a series of complicated in-vivo chemical reactions. The BL is initiated by the enzymatic oxidation of luciferin (LH2). However, the mechanism of the efficient spin-forbidden oxygenation is far from being totally understood. Via MD simulation and QM/MM calculations, this article describes the complete process of oxygenation in real protein. The oxygenation of luciferin is initiated by a single electron transfer from the trivalent anionic LH2 (L3−) to O2 to form 1[L•2−…O2•−]; the entire reaction is carried out along the ground-state potential energy surface to produce the dioxetanone (FDO−) via three transition states and two intermediates. The low energy barriers of the oxygenation reaction and biradical annihilation involved in the reaction explain this spin-forbidden reaction with high efficiency. This study is helpful for understanding the BL initiation of fireflies and the other oxygen-dependent bioluminescent organisms.

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5

Tang, Conghui, Xu Qiu, Zengrui Cheng, and Ning Jiao. "Molecular oxygen-mediated oxygenation reactions involving radicals." Chemical Society Reviews 50, no. 14 (2021): 8067–101. http://dx.doi.org/10.1039/d1cs00242b.

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Molecular oxygen as a green, inexpensive oxidant and oxygen source has displayed lots of advantages compared to other oxidants. This review introduces the recent advances of radical processes in molecular oxygen-mediated oxygenation reactions.

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6

Cheng, Xiaokai, Xingen Hu, and Zhan Lu. "Visible-Light-Promoted Aerobic Homogenous Oxygenation Reactions." Chinese Journal of Organic Chemistry 37, no. 2 (2017): 251. http://dx.doi.org/10.6023/cjoc201609022.

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7

Fukuzumi, Shunichi, Yong‐Min Lee, and Wonwoo Nam. "Photocatalytic Oxygenation Reactions Using Water and Dioxygen." ChemSusChem 12, no. 17 (July 25, 2019): 3931–40. http://dx.doi.org/10.1002/cssc.201901276.

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8

Perez, Daniel I., Maria Mifsud Grau, Isabel W. C. E. Arends, and Frank Hollmann. "Visible light-driven and chloroperoxidase-catalyzed oxygenation reactions." Chemical Communications, no. 44 (2009): 6848. http://dx.doi.org/10.1039/b915078a.

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9

Mihara, Satoru, and Hideki Tateba. "Photosensitized oxygenation reactions of phytol and its derivatives." Journal of Organic Chemistry 51, no. 7 (April 1986): 1142–44. http://dx.doi.org/10.1021/jo00357a043.

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10

MONTANARI, F., S. BANFI, G. POZZI, and S. QUICI. "ChemInform Abstract: Oxygenation Reactions under Two-Phase Conditions." ChemInform 26, no. 20 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199520261.

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11

Bian, Changliang, Atul K. Singh, Linbin Niu, Hong Yi, and Aiwen Lei. "Visible‐Light‐Mediated Oxygenation Reactions using Molecular Oxygen." Asian Journal of Organic Chemistry 6, no. 4 (February 27, 2017): 386–96. http://dx.doi.org/10.1002/ajoc.201600563.

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12

Šagud, Ivana, and Irena Škorić. "Photocatalytic Oxygenation by Water-Soluble Metalloporphyrins as a Pathway to Functionalized Polycycles." International Journal of Photoenergy 2018 (December 30, 2018): 1–8. http://dx.doi.org/10.1155/2018/1017957.

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Photocatalytic processes are present in natural biochemical pathways as well as in the organic synthetic ones. This minireview will cover the field of photocatalysis that uses both the free-base and specially metallated porphyrins as catalysts. While free-base porphyrins are valuable sensitizers to output singlet oxygen, metalloporphyrins are even more adjustable as photocatalysts because of their coordination capacity, generating a wider range of oxidation reactions. They can be applied in autooxidation reactions, hydroxylations, or direct oxygen transfer producing epoxides. This review will mainly focus on how manganese and some iron porphyrins can be utilized for the functionalization of compounds that have a polycyclic skeleton in their structure. These kinds of compounds are notoriously taxing to obtain and difficult to further functionalize by conventional organic synthetic methods. We have focused on photocatalytic oxygenation reactions in mild conditions with the use of water-soluble porphyrins, as this has been proven to be a good tool for these transformations. In the photocatalytic reactions of some polycyclic heteroaromatic compounds, new polycyclic epoxides, enediones, ketones, alcohols, and/or hydroperoxides are yielded, depending on the catalyst applied. The application of anionic and cationic Mn(III) porphyrins under different reaction parameters results in different reaction pathways generating a vast number of photocatalytic products. Recently, Co and Ni complexes have been also photophysically investigated and confirmed as potential photocatalysts for the functionalization of organic substrates.

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13

TAKAGUCHI, YUTAKA, TAKAAKI TSUBOI, YUUKI SAKO, and SADAO TSUBOI. "SYNTHESIS OF FULLERODENDRON AND ITS PHOTOCATALITIC ACTIVITY." International Journal of Nanoscience 05, no. 04n05 (August 2006): 593–97. http://dx.doi.org/10.1142/s0219581x0600484x.

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A newly designed fullerodendron was synthesized in good yield (84%) by the use of a Diels-Alder reaction of C 60 with an anthryl dendron. Interestingly, the fullerodendron acts as a new catalyst that uses oxygen and light to generate singlet oxygen (1 O 2). The dendron facilitates various types of singlet oxygenation reactions including ene reaction, Diels-Alder reaction, and oxidation of phenol and sulfide.

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14

Мальцева and L. Maltseva. "Hyperoxia effect on humoral and cell components of immunobiological resistance of healthy rats in experiment." Journal of New Medical Technologies. eJournal 8, no. 1 (November 5, 2014): 1–6. http://dx.doi.org/10.12737/4112.

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The paper contains information about hyperbaric oxygenation impact on humoral and cell components of immune-biological resistance of healthy rats. The following factors are analyzed: potency of oxygen-dependent enzyme systems (myeloperoxidase, oxidase), oxygen-independent systems (leukocyte lysozyme, cationic proteins), killing reactions of peripheral blood neutrophils, their phagocytic and oxidase reserve, complement activity and content of circulating immune complexes in the blood serum of healthy animals, which have been exposed to 60-minute sessions of hyperbaric oxygenation, over time from the 1st to the 30th day post hyperoxia period during experiment. A single session of hyperbaric oxygenation is carried out within 60 minutes (3 absolute atmospheres mode). Mechanisms of adaptation and pathological reactions formation by immune-biological surveillance system of healthy body in early and late post hyperoxia periods during experiment are considered. The paper shows that adaptive responses, which are designed to protect the body against aggressive action of oxygen under the influence of hyperbaric oxygenation, are formed in the bodies of healthy animals. The reactions of oxygen-dependent of phagocytes systems in conditions of hyperoxia manifested in the early stages of the research, persisting to the end of the observation and the reactions of oxygen independent - only at early stages. The humoral responses of healthy organism under hyperbaric oxygen are characterized by the change in complement activity and concentration of circulating immune complexes in blood serum. The received experimental data may be used as a theoretical explanation of indications for use of hyperbaric oxygen therapy and different hyperbaric oxygenation regimes.

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15

Mlakić, Milena, Anita Šalić, Matea Bačić, Bruno Zelić, Ivana Šagud, Ottó Horváth, and Irena Škorić. "Photocatalytic Oxygenation of Heterostilbenes—Batch versus Microflow Reactor." Catalysts 11, no. 3 (March 20, 2021): 395. http://dx.doi.org/10.3390/catal11030395.

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On the basis of earlier results with furan and thiophene derivatives of benzobicyclo[3.2.1]octadiene, photocatalytic oxygenation of novel furo- and thieno heterostilbenes with water-soluble manganese(III) porphyrins offered suitable possibilities to study their reactivities and reaction pathways depending on the heteroatom and the catalyst charge. The experiments were carried out in two reactors types (batch and microflow) to investigate the geometric effects. NMR spectroscopy, GC, and UPLC/MS analyses were applied for identification and quantification of the products. As our results indicated, the 2-thienyl and the common p-tolyl groups in the starting compounds remained intact due to their stronger aromaticity. Hence, the thieno derivative underwent oxygenation only at the open-chain part of the molecule, and the rates of its reactions were much lower than those of the furyl analogue. The less stable furan ring was easily oxygenated, its products with highest ratios were 2-furanon derivatives. Epoxide formation occurred at the open-chain parts of both substrates preferably by the anionic catalyst. Nevertheless, the conversion rates of the substrates were higher with the cationic porphyrin, according to electrophilic attacks by photogenerated Mn(V)=O species. Additionally, the reactions were significantly faster in microflow reactors due to the more favorable circumstances of mass transfer, diffusion, and light penetration.

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16

Vuk, Dragana, Ottó Horváth, and Irena Škorić. "New Functionalized Polycycles Obtained by Photocatalytic Oxygenation Using Mn(III) Porphyrins in Basic Media." Catalysts 9, no. 4 (March 27, 2019): 304. http://dx.doi.org/10.3390/catal9040304.

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According to our earlier observations, the products of photocatalytic oxygenations of furan and thiophene derivatives of benzobicyclo[3.2.1]octadiene with anionic and cationic manganese(III) porphyrin at pH = 7 strongly depended on the type and position of the heteroatom in the aromatic ring, as well as the charge of the photocatalyst. Hence, a significant pH increase (to 10) in these systems offered a reasonable tool to affect the diversity and yields of the oxygenation products. They were quantitatively separated by TLC and identified with NMR analyses. The results clearly indicated that the increase of HO− concentration, in most cases, considerably changed the product yield, e.g., enhanced it to 70% for the hydroxy-furyl derivative. Accordingly, the selectivity of the oxygenation of the furan compound could be improved in this way. In the case of one thienyl compound, however, even an additional product appeared, while the yields of the products of the other thiophene derivative (with cationic catalyst) decreased to zero, suggesting the application of lower pH for preparative purposes. The pH effects indicate that oxygenation reactions in these systems involve more photochemically generated oxidative agents, e.g., •OH and (P)Mn(V)=O), the role of which is affected by the pH increase in various ways.

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17

Paul, Melanie, Alexander Hoffmann, and Sonja Herres-Pawlis. "Room temperature stable multitalent: highly reactive and versatile copper guanidine complexes in oxygenation reactions." JBIC Journal of Biological Inorganic Chemistry 26, no. 2-3 (February 17, 2021): 249–63. http://dx.doi.org/10.1007/s00775-021-01849-9.

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AbstractInspired by the efficiency of natural enzymes in organic transformation reactions, the development of synthetic catalysts for oxygenation and oxidation reactions under mild conditions still remains challenging. Tyrosinases serve as archetype when it comes to hydroxylation reactions involving molecular oxygen. We herein present new copper(I) guanidine halide complexes, capable of the activation of molecular oxygen at room temperature. The formation of the reactive bis(µ-oxido) dicopper(III) species and the influence of the anion are investigated by UV/Vis spectroscopy, mass spectrometry, and density functional theory. We highlight the catalytic hydroxylation activity towards diverse polycyclic aromatic alcohols under mild reaction conditions. The selective formation of reactive quinones provides a promising tool to design phenazine derivatives for medical applications. Graphic abstract

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18

Liang, Yujie, Shi-Hui Shi, Rui Jin, Xu Qiu, Jialiang Wei, Hui Tan, Xue Jiang, Xiaomeng Shi, Song Song, and Ning Jiao. "Electrochemically induced nickel catalysis for oxygenation reactions with water." Nature Catalysis 4, no. 2 (January 11, 2021): 116–23. http://dx.doi.org/10.1038/s41929-020-00559-w.

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19

Kalyani, Dipannita, and Melanie S. Sanford. "Regioselectivity in Palladium-Catalyzed C−H Activation/Oxygenation Reactions." Organic Letters 7, no. 19 (September 2005): 4149–52. http://dx.doi.org/10.1021/ol051486x.

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20

Limberg, Christian. "The Role of Radicals in Metal-Assisted Oxygenation Reactions." Angewandte Chemie International Edition 42, no. 48 (December 15, 2003): 5932–54. http://dx.doi.org/10.1002/anie.200300578.

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21

MEUNIER, B., and S. CAMPESTRINI. "ChemInform Abstract: Oxygenation Reactions Catalyzed by Supported Sulfonated Metalloporphyrins." ChemInform 24, no. 46 (August 20, 2010): no. http://dx.doi.org/10.1002/chin.199346305.

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22

Benders, Stefan, Florian Strassl, Bastian Fenger, Bernhard Blümich, Sonja Herres-Pawlis, and Markus Küppers. "Imaging of copper oxygenation reactions in a bubble flow." Magnetic Resonance in Chemistry 56, no. 9 (May 17, 2018): 826–30. http://dx.doi.org/10.1002/mrc.4742.

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23

Konrad, David, Bilal Kicin, and Dirk Trauner. "Concise Asymmetric Synthesis of Kweichowenol A." Synlett 30, no. 04 (December 17, 2018): 383–86. http://dx.doi.org/10.1055/s-0037-1610390.

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An asymmetric 11-step synthesis of the polyoxygenated cyclohexene natural product kweichowenol A from the traditional Chinese medicinal herb Uvaria kweichowesis is reported. The oxygenation pattern was installed on a linear precursor by exploiting the acyclic stereocontrol of the Kiyooka aldol reaction, as well as Cram chelate-controlled Grignard reactions. Ring-closing metathesis and a selective benzoylation then gave the natural product.

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24

Yang, Chun-Hua, Wen-Wen Fan, Gong-Qing Liu, Lili Duan, Lin Li, and Yue-Ming Li. "On the understanding of BF3·Et2O-promoted intra- and intermolecular amination and oxygenation of unfunctionalized olefins." RSC Advances 5, no. 75 (2015): 61081–93. http://dx.doi.org/10.1039/c5ra10513g.

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BF₃·Et₂O was found to be effective for the amination and oxygenation of unfunctionalized olefins. In the presence of 3 equiv. of BF₃·Et₂O, intra- and intermolecular amination and oxygenation reactions could be realized in up to 99% isolated yields.

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25

Lindhorst, A. C., S. Haslinger, and Fritz E. Kühn. "Molecular iron complexes as catalysts for selective C–H bond oxygenation reactions." Chemical Communications 51, no. 97 (2015): 17193–212. http://dx.doi.org/10.1039/c5cc07146a.

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26

Schendera, Eva, Alexander Villinger, and Malte Brasholz. "Photoinduced iodine-mediated tandem dehydrogenative Povarov cyclisation/C–H oxygenation reactions." Organic & Biomolecular Chemistry 18, no. 35 (2020): 6912–15. http://dx.doi.org/10.1039/d0ob01494j.

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27

Fukuzumi, Shunichi, Yong-Min Lee, and Wonwoo Nam. "Photocatalytic redox reactions with metalloporphyrins." Journal of Porphyrins and Phthalocyanines 24, no. 01n03 (January 2020): 21–32. http://dx.doi.org/10.1142/s1088424619300131.

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Metalloporphyrinoids are utilized as efficient sensitizers and catalysts in photosynthesis and the reverse reaction that is respiration. Because metalloporphyrinoids show strong absorption in the visible region and redox active, metalloporphyrinoids are also suited as photoredox catalysts for photo-driven redox reactions using solar energy. In particular, metalloporphyrins are utilized as pivotal components to mimic the structure and function of the photosynthetic reaction center. Metalloporphyrins are used as photoredox catalysts for hydrogen evolution from electron and proton sources combining hydrogen evolution catalysts. Metalloporphyrins also act as thermal redox catalysts for photocatalytic reduction of CO2 with photoredox catalysts. Metalloporphyrins are also used as dual catalysts for a photoredox catalyst for oxygenation of substrates with H2O and a redox catalyst for O2 reduction when dioxygen is used as a two-electron oxidant and H2O as an oxygen source, both of which are the greenest reactants. Free base porphyrins can also be employed as promising photoredox catalysts for C–C bond formation reactions.

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28

Yang, Lili, Fang Wang, Jiali Gao, and Yong Wang. "What factors tune the chemical equilibrium between metal-iodosylarene oxidants and high-valent metal-oxo ones?" Physical Chemistry Chemical Physics 21, no. 3 (2019): 1271–76. http://dx.doi.org/10.1039/c8cp06117c.

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29

Szakács, Zoltán, Mihály Kállay, and Miklós Kubinyi. "Theoretical study on the photooxygenation and photorearrangement reactions of 3-hydroxyflavone." RSC Advances 7, no. 51 (2017): 32185–92. http://dx.doi.org/10.1039/c7ra04590e.

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The mechanisms of three photodegradation reactions of 3-hydroxyflavone – its photosensitized oxygenation, photooxygenation with ³O₂ and photorearrangement into an indanedione derivative – have been investigated by computing the free energy profiles.

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30

Nehru, Kasi, Soo Jeong Kim, In Young Kim, Mi Sook Seo, Youngmee Kim, Sung-Jin Kim, Jinheung Kim, and Wonwoo Nam. "A highly efficient non-heme manganese complex in oxygenation reactions." Chemical Communications, no. 44 (2007): 4623. http://dx.doi.org/10.1039/b708976g.

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31

Bonaventura, Celia, Robert Henkens, Abdu I. Alayash, Sambuddha Banerjee, and Alvin L. Crumbliss. "Molecular Controls of the Oxygenation and Redox Reactions of Hemoglobin." Antioxidants & Redox Signaling 18, no. 17 (June 10, 2013): 2298–313. http://dx.doi.org/10.1089/ars.2012.4947.

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32

Hetterscheid, Dennis G. H., and Bas de Bruin. "Open-shell rhodium and iridium species in (catalytic) oxygenation reactions." Journal of Molecular Catalysis A: Chemical 251, no. 1-2 (May 2006): 291–96. http://dx.doi.org/10.1016/j.molcata.2006.02.009.

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33

Gollnick, Klaus, and Stephan Held. "Hydroxyanthraquinones as sensitizers of electron-transfer-induced photo-oxygenation reactions." Journal of Photochemistry and Photobiology A: Chemistry 70, no. 2 (February 1993): 135–45. http://dx.doi.org/10.1016/1010-6030(93)85033-5.

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34

Yoon, Jihae, Samuel A Wilson, Yu Kyeong Jang, Mi Sook Seo, Kasi Nehru, Britt Hedman, Keith O Hodgson, Eckhard Bill, Edward I Solomon, and Wonwoo Nam. "Reactive Intermediates in Oxygenation Reactions with Mononuclear Nonheme Iron Catalysts." Angewandte Chemie International Edition 48, no. 7 (January 9, 2009): 1257–60. http://dx.doi.org/10.1002/anie.200802672.

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35

Yoon, Jihae, Samuel A Wilson, Yu Kyeong Jang, Mi Sook Seo, Kasi Nehru, Britt Hedman, Keith O Hodgson, Eckhard Bill, Edward I Solomon, and Wonwoo Nam. "Reactive Intermediates in Oxygenation Reactions with Mononuclear Nonheme Iron Catalysts." Angewandte Chemie 121, no. 7 (January 9, 2009): 1283–86. http://dx.doi.org/10.1002/ange.200802672.

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36

Jiang, Yi-Fan, Cheng-Zong Yuan, Xiao Zhou, Hong-Li Guo, Ya-Nan Liu, Nan Jiang, and An-Wu Xu. "Highly efficient redox-driven reversible color switching of dye molecules via hydrogenation/oxygenation." Chemical Communications 53, no. 2 (2017): 360–63. http://dx.doi.org/10.1039/c6cc08500h.

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37

Liu, Ya-Nan, Xiao Zhou, Xin Wang, Kuang Liang, Zheng-Kun Yang, Cong-Cong Shen, M. Imran, Shafaq Sahar, and An-Wu Xu. "Hydrogenation/oxidation induced efficient reversible color switching between methylene blue and leuco-methylene blue." RSC Advances 7, no. 48 (2017): 30080–85. http://dx.doi.org/10.1039/c7ra04498d.

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38

Li, Ze-lin, Kang-kang Sun, and Chun Cai. "Nickel-catalyzed regioselective C–H oxygenation: new routes for versatile C–O bond formation." Organic Chemistry Frontiers 6, no. 5 (2019): 637–42. http://dx.doi.org/10.1039/c8qo01274a.

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Nickel-catalyzed regioselective C–H oxygenation reactions of chelating arenes using iodobenzene diacetate, alcohols, and benzoic acids respectively as attacking reagents have been developed for the first time.

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39

Ferraro, Daniel J., Adam Okerlund, Eric Brown, and S. Ramaswamy. "One enzyme, many reactions: structural basis for the various reactions catalyzed by naphthalene 1,2-dioxygenase." IUCrJ 4, no. 5 (August 8, 2017): 648–56. http://dx.doi.org/10.1107/s2052252517008223.

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Rieske nonheme iron oxygenases (ROs) are a well studied class of enzymes. Naphthalene 1,2-dioxygenase (NDO) is used as a model to study ROs. Previous work has shown how side-on binding of oxygen to the mononuclear iron provides this enzyme with the ability to catalyze stereospecific and regiospecificcis-dihydroxylation reactions. It has been well documented that ROs catalyze a variety of other reactions, including mono-oxygenation, desaturation, O- and N-dealkylation, sulfoxidationetc. NDO itself catalyzes a variety of these reactions. Structures of NDO in complex with a number of different substrates show that the orientation of the substrate in the active site controls not only the regiospecificity and stereospecificity, but also the type of reaction catalyzed. It is proposed that the mononuclear iron-activated dioxygen attacks the atoms of the substrate that are most proximal to it. The promiscuity of delivering two products (apparently by two different reactions) from the same substrate can be explained by the possible binding of the substrate in slightly different orientations aided by the observed flexibility of residues in the binding pocket.

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40

Fukuzumi, Shunichi. "Electron transfer and catalysis with high-valent metal-oxo complexes." Dalton Transactions 44, no. 15 (2015): 6696–705. http://dx.doi.org/10.1039/c5dt00204d.

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41

Saleem-Batcha, Raspudin, Frederick Stull, Jacob N. Sanders, Bradley S. Moore, Bruce A. Palfey, K. N. Houk, and Robin Teufel. "Enzymatic control of dioxygen binding and functionalization of the flavin cofactor." Proceedings of the National Academy of Sciences 115, no. 19 (April 23, 2018): 4909–14. http://dx.doi.org/10.1073/pnas.1801189115.

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The reactions of enzymes and cofactors with gaseous molecules such as dioxygen (O2) are challenging to study and remain among the most contentious subjects in biochemistry. To date, it is largely enigmatic how enzymes control and fine-tune their reactions with O2, as exemplified by the ubiquitous flavin-dependent enzymes that commonly facilitate redox chemistry such as the oxygenation of organic substrates. Here we employ O2-pressurized X-ray crystallography and quantum mechanical calculations to reveal how the precise positioning of O2 within a flavoenzyme’s active site enables the regiospecific formation of a covalent flavin–oxygen adduct and oxygenating species (i.e., the flavin-N5-oxide) by mimicking a critical transition state. This study unambiguously demonstrates how enzymes may control the O2 functionalization of an organic cofactor as prerequisite for oxidative catalysis. Our work thus illustrates how O2 reactivity can be harnessed in an enzymatic environment and provides crucial knowledge for future rational design of O2-reactive enzymes.

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42

Zhou, Xin-Yan, Bo Fu, Wen-Dong Jin, Xiong Wang, Ke-Ke Wang, Mei Wang, Yuan-Bin She, and Hai-Min Shen. "Efficient and Selective Oxygenation of Cycloalkanes and Alkyl Aromatics with Oxygen through Synergistic Catalysis of Bimetallic Active Centers in Two-Dimensional Metal-Organic Frameworks Based on Metalloporphyrins." Biomimetics 8, no. 3 (July 21, 2023): 325. http://dx.doi.org/10.3390/biomimetics8030325.

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Confined catalytic realms and synergistic catalysis sites were constructed using bimetallic active centers in two-dimensional metal-organic frameworks (MOFs) to achieve highly selective oxygenation of cycloalkanes and alkyl aromatics with oxygen towards partly oxygenated products. Every necessary characterization was carried out for all the two-dimensional MOFs. The selective oxygenation of cycloalkanes and alkyl aromatics with oxygen was accomplished with exceptional catalytic performance using two-dimensional MOF Co-TCPPNi as a catalyst. Employing Co-TCPPNi as a catalyst, both the conversion and selectivity were improved for all the hydrocarbons investigated. Less disordered autoxidation at mild conditions, inhibited free-radical diffusion by confined catalytic realms, and synergistic C–H bond oxygenation catalyzed by second metal center Ni employing oxygenation intermediate R–OOH as oxidant were the factors for the satisfying result of Co-TCPPNi as a catalyst. When homogeneous metalloporphyrin T(4-COOCH3)PPCo was replaced by Co-TCPPNi, the conversion in cyclohexane oxygenation was enhanced from 4.4% to 5.6%, and the selectivity of partly oxygenated products increased from 85.4% to 92.9%. The synergistic catalytic mechanisms were studied using EPR research, and a catalysis model was obtained for the oxygenation of C–H bonds with O2. This research offered a novel and essential reference for both the efficient and selective oxygenation of C–H bonds and other key chemical reactions involving free radicals.

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Yang, Hsuan, Chia-Pei Chung, Ying-Chih Lin, and Yi-Hong Liu. "Facile oxygenation reactions of ruthenium acetylide complex containing substituted olefinic group." Dalton Transactions 40, no. 14 (2011): 3703. http://dx.doi.org/10.1039/c0dt01551b.

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44

Bremner, David H., and Neil S. Ringan. "Chemistry of cephems: C-4 substitution and sulphoxide de-oxygenation reactions." Journal of the Chemical Society, Perkin Transactions 1, no. 5 (1991): 1265. http://dx.doi.org/10.1039/p19910001265.

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45

Matsui, Toshitaka, Masaki Unno, and Masao Ikeda-Saito. "Heme Oxygenase Reveals Its Strategy for Catalyzing Three Successive Oxygenation Reactions." Accounts of Chemical Research 43, no. 2 (February 16, 2010): 240–47. http://dx.doi.org/10.1021/ar9001685.

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46

Fukuzumi, Shunichi, Takashi Kishi, Hiroaki Kotani, Yong-Min Lee, and Wonwoo Nam. "Highly efficient photocatalytic oxygenation reactions using water as an oxygen source." Nature Chemistry 3, no. 1 (November 28, 2010): 38–41. http://dx.doi.org/10.1038/nchem.905.

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47

Yuan, Zhiwen, and Jeanne M. VanBriesen. "Yield prediction and stoichiometry of multi-step biodegradation reactions involving oxygenation." Biotechnology and Bioengineering 80, no. 1 (August 15, 2002): 100–113. http://dx.doi.org/10.1002/bit.10355.

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48

Akaba, Ryoichi, Masaki Kamata, Akiko Koike, Ken-Ichi Mogi, Yasunao Kuriyama, and Hirochika Sakuragi. "Thiapyrylium salt-sensitized electron transfer reactions oftrans-stilbene. Dimerization and oxygenation." Journal of Physical Organic Chemistry 10, no. 11 (November 1997): 861–69. http://dx.doi.org/10.1002/(sici)1099-1395(199711)10:11<861::aid-pca947>3.0.co;2-l.

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KHAN, M. M. T. "ChemInform Abstract: Oxidation and Oxygenation Reactions Catalyzed by Ruthenium(III) Complexes." ChemInform 23, no. 50 (September 1, 2010): no. http://dx.doi.org/10.1002/chin.199250302.

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50

Balestra, Costantino, and Jacek Kot. "Oxygen: A Stimulus, Not “Only” a Drug." Medicina 57, no. 11 (October 25, 2021): 1161. http://dx.doi.org/10.3390/medicina57111161.

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Depending on the oxygen partial pressure in a tissue, the therapeutic effect of oxygenation can vary from simple substance substitution up to hyperbaric oxygenation when breathing hyperbaric oxygen at 2.5–3.0 ATA. Surprisingly, new data showed that it is not only the oxygen supply that matters as even a minimal increase in the partial pressure of oxygen is efficient in triggering cellular reactions by eliciting the production of hypoxia-inducible factors and heat-shock proteins. Moreover, it was shown that extreme environments could also interact with the genome; in fact, epigenetics appears to play a major role in extreme environments and exercise, especially when changes in oxygen partial pressure are involved. Hyperbaric oxygen therapy is, essentially, “intermittent oxygen” exposure. We must investigate hyperbaric oxygen with a new paradigm of treating oxygen as a potent stimulus of the molecular network of reactions.

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