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Journal articles on the topic '2-dioxetano'

Author: Grafiati

Published: 4 June 2021

Last updated: 3 February 2022

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1

Ijuin, Hisako K., Masaki Yamada, Mamoru Ohashi, Nobuko Watanabe, and Masakatsu Matsumoto. "Electron-Transfer-Induced Decomposition of 1,2-Dioxetanes in Negative-Mode Matrix-Assisted Laser Desorption/Ionization Time-of-Flight Mass Spectrometry." European Journal of Mass Spectrometry 14, no. 1 (2008): 17–25. http://dx.doi.org/10.1255/ejms.903.

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1,2-Dioxetanes bearing an aromatic electron donor undergo intramolecular charge-transfer-induced chemiluminescence (CTICL). Although there has been some controversy regarding the mechanisms involved, there is little experimental evidence to strongly support any of the proposed mechanisms. In the course of our investigations, to clarify these mechanisms, we tried to effectively ionize dioxetanes bearing a phenolic group and found that poly(3-octylthiophene-2,5-diyl) was a promising matrix for negative-mode matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-ToF-M

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2

Cao, J., R. Lopez, J. M. Thacker, et al. "Chemiluminescent probes for imaging H2S in living animals." Chemical Science 6, no. 3 (2015): 1979–85. http://dx.doi.org/10.1039/c4sc03516j.

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Responsive 1,2-dioxetane chemiluminescent probes have been developed that display instantaneous, sensitive, and selective responses to H<sub>2</sub>S and are capable of imaging H<sub>2</sub>S in living mice.

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3

Watanabe, Nobuko, Miho Ichikawa, Ayumi Ono, Hiroyuki Murakami, and Masakatsu Matsumoto. "New Triggering System for Dioxetane-based Chemiluminescence: Base-induced Decomposition of Bicyclic Dioxetanes Bearing a 3-Aminophenyl or 2-Phenylindol-6-yl Moiety." Chemistry Letters 34, no. 5 (2005): 718–19. http://dx.doi.org/10.1246/cl.2005.718.

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4

Matsumoto, Masakatsu, Nobuko Watanabe, Tamaki Shiono, Hiroyuki Suganuma, and Jyunya Matsubara. "Chemiluminescence of spiro[1,2-dioxetane-3,1′-dihydroisobenzofuran]s, spiro[1,2-dioxetane-3,1′-isochroman]s and a spiro[1,2-dioxetane-3,1′-(2-benzoxepane)]." Tetrahedron Letters 38, no. 33 (1997): 5825–28. http://dx.doi.org/10.1016/s0040-4039(97)01332-4.

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5

Pola, Josef, and Josef Vítek. "Continuous wave CO2 laser driven oxidation of 2-butene and 2-octafluorobutene." Collection of Czechoslovak Chemical Communications 54, no. 11 (1989): 3083–87. http://dx.doi.org/10.1135/cccc19893083.

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CW CO2 laser induced reactions of 2-butene and 2-octafluorobutene with molecular ground state 3O2 oxygen in the presence of sulfur hexafluoride afford products that can be rationalized by means of the earlier proposed mechanism involving transient dioxetane and its cleavage into carbonyl compounds.

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6

Seven, Ozlem, Fazli Sozmen, and Ilke Simsek Turan. "Self immolative dioxetane based chemiluminescent probe for H 2 O 2 detection." Sensors and Actuators B: Chemical 239 (February 2017): 1318–24. http://dx.doi.org/10.1016/j.snb.2016.09.120.

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7

Bronstein, I., J. C. Voyta, G. H. Thorpe, L. J. Kricka, and G. Armstrong. "Chemiluminescent assay of alkaline phosphatase applied in an ultrasensitive enzyme immunoassay of thyrotropin." Clinical Chemistry 35, no. 7 (1989): 1441–46. http://dx.doi.org/10.1093/clinchem/35.7.1441.

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Abstract We compared a chemiluminescent assay and a colorimetric endpoint assay for measuring an alkaline phosphatase (EC 3.1.3.1) label in an enzyme immunoassay of thyrotropin (TSH). The substrate in the chemiluminescent assay is a derivative of adamantyl 1,2-dioxetane phosphate. On dephosphorylation, catalyzed by alkaline phosphatase, the 1,2-dioxetane decomposes further and emits a glow of light (lambda max 470 nm). We modified the Hybritech Tandem-E TSH High Sensitivity assay for chemiluminescent detection of bound alkaline phosphatase label by using this substrate (with 20-, 40-, and 60-m

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8

Schaap, A. Paul, Tsae-Shyan Chen, Richard S. Handley, Renuka DeSilva, and Brij P. Giri. "Chemical and enzymatic triggering of 1,2-dioxetanes. 2: fluoride-induced chemiluminescence from tert-butyldimethylsilyloxy-substituted dioxetanes." Tetrahedron Letters 28, no. 11 (1987): 1155–58. http://dx.doi.org/10.1016/s0040-4039(00)95313-9.

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9

Thorpe, G. H., I. Bronstein, L. J. Kricka, B. Edwards, and J. C. Voyta. "Chemiluminescent enzyme immunoassay of alpha-fetoprotein based on an adamantyl dioxetane phenyl phosphate substrate." Clinical Chemistry 35, no. 12 (1989): 2319–21. http://dx.doi.org/10.1093/clinchem/35.12.2319.

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Abstract We have evaluated a new chemiluminescent substrate for the alkaline phosphatase (EC 3.1.3.1) label used in a Hybritech Tandem-E immunoassay of alpha-fetoprotein (AFP). The new substrate, adamantyl 1,2-dioxetane phenyl phosphate (AMPPD), emits light at 477 nm when acted upon by the enzyme. Detection limits for AFP with this method were 33 ng/L (mean of 20 replicates of the zero standard + 2 SD) and 470 ng/L (twice background). Between-batch CVs ranged from 4.31% to 9.60% for AFP in the range 29.1-132.0 micrograms/L. Comparison of results for 49 specimens assayed with use of the chemilu

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10

Matsumoto, Masakatsu, Tatsuji Hiroshima, Shuichi Chiba, Ryo Isobe, Nobuko Watanabe, and Hisako Kobayashi. "Synthesis of 3-ethoxy-4,4-diisopropyl-1,2-dioxetanes bearing a benzo(b)furan-2-yl or a benzo(b)thiophen-2-yl group: CIEEL-active dioxetanes emitting red light." Luminescence 14, no. 6 (1999): 345–48. http://dx.doi.org/10.1002/(sici)1522-7243(199911/12)14:6<345::aid-bio559>3.0.co;2-t.

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11

Adam, Waldemar, Chantu R. Saha-Möller, and Simon B. Schambony. "A Highly Diastereoselective Dioxetane Formation by the Hydroxy-Directed [2+2] Cycloaddition of Singlet Oxygen to a Chiral Allylic Alcohol." Journal of the American Chemical Society 121, no. 9 (1999): 1834–38. http://dx.doi.org/10.1021/ja9835077.

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12

Matsumoto, Masakatsu, Nobuko Watanabe, Hisako Kobayashi, Mitsunori Azami, and Hiroshi Ikawa. "Synthesis and chemiluminescence of 3,3-diisopropyl-4-methoxy-4-(2-naphthyl)-1,2-dioxetanes." Tetrahedron Letters 38, no. 3 (1997): 411–14. http://dx.doi.org/10.1016/s0040-4039(96)02312-x.

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13

Jurasek, Lubo, Lívia Kritofová, Yujun Sun, and Dimitris S. Argyropoulos. "Alkaline oxidative degradation of diphenylmethane structures Activation energy and computational analysis of the reaction mechanism." Canadian Journal of Chemistry 79, no. 9 (2001): 1394–401. http://dx.doi.org/10.1139/v01-118.

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A diphenylmethane model compound (2,2'-methylenebis[6-methoxy-4-methylphenol]) and residual kraft lignin were treated with alkaline hydrogen peroxide. Kinetic data for the disappearance of the model and the diphenylmethane structures in the residual lignin was collected. The activation energies for the degradation were found to be similar (54 ± 11 kJ mol1 for the model and 58 ± 5 kJ mol1 for the residual lignin). A comparison of the activation energies with the data of a previous study on a biphenyl model compound (3,3'-dimethoxy-5,5'-dimethyl-[1,1'-biphenyl]-2,2'-diol) showed a substantiall

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14

Kopecky, Karl R., Yu Xie, and José Molina. "Dioxirane formation in ozonolysis of E- and Z-1,2-dimethoxy-1,2-diphenylethene." Canadian Journal of Chemistry 71, no. 2 (1993): 272–74. http://dx.doi.org/10.1139/v93-039.

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Addition of ozone to E- or Z-1,2-dimethoxy-1,2-diphenylethene, E- or Z-1, in inert solvents results in formation of ~1 mole of methyl benzoate, ~0.5 and ~0.1 mole of the corresponding oxiranes 2 and dioxetanes 3, respectively, and 0.03 mole of 3,6-dimethoxy-3,6-diphenyl-1,2,4,5-tetroxane 4 at −20 °C. Product distributions vary with starting material, initial concentration, extent of reaction, and temperature. At −70 °C ~0.3 mole of trans-2 and 0.2 mole of cis-and trans-4 are formed from E-1. Addition of E- or Z-1 to solutions of excess ozone results in formation of up to 0.7 mole of (methoxy)p

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15

Kawamura, Yasuhiko, Takaaki Ishiduka, and Masao Tsukayama. "One-Way Geometrical Isomerization of 1,1-Diarylethenes Induced by Photosensitized Electron Transfer." International Journal of Modern Physics B 17, no. 08n09 (2003): 1492–97. http://dx.doi.org/10.1142/s0217979203019216.

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One-way geometrical isomerization around a C=C bond of 1,1-diary1-2-t-butylethene is achieved upon photoirradiation of cyanoaromatics as a light-absorbing sensitizer. In the thermochemical view, there is no difference between both E and Z isomers of the ethene. Key intermediate is a putative distonic radical cation which is a unique one having a spatially separate radical and ionic centers on the molecular framework. Generation of such an intermediate is due to the presence of a π-donating substituent on an aromatic ring and a bulky t-butyl group. Molecular oxygen interacts as superoxide with

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16

Matsumoto, Masakatsu, Masatoshi Tanimura, Taichi Akimoto, Nobuko Watanabe, and Hisako K. Ijuin. "Solvent-promoted chemiluminescent decomposition of a bicyclic dioxetane bearing a 4-(benzothiazol-2-yl)-3-hydroxyphenyl moiety." Tetrahedron Letters 49, no. 26 (2008): 4170–73. http://dx.doi.org/10.1016/j.tetlet.2008.04.110.

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17

Adam, Waldemar, Franklin Vargas, Bernd Epe, Dietmar Schiffmann, and Dieter Wild. "Single-Electron-Transfer in the Reduction of 1, 2-Dioxetanes by Biologically Active Substrates." Free Radical Research Communications 5, no. 4-5 (1989): 253–58. http://dx.doi.org/10.3109/10715768909074708.

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18

Bronstein, I., C. S. Martin, J. J. Fortin, C. E. Olesen, and J. C. Voyta. "Chemiluminescence: sensitive detection technology for reporter gene assays." Clinical Chemistry 42, no. 9 (1996): 1542–46. http://dx.doi.org/10.1093/clinchem/42.9.1542.

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Abstract A series of enzyme-activated chemiluminescence-based assays of reporter gene expression, useful in many biomedical applications, has been developed. The chemiluminescence detection systems for beta-galactosidase, beta-glucuronidase (GUS), and secreted placental alkaline phosphatase (SEAP) reporter enzymes are all based on use of 1,2-dioxetane substrates. This detection technology also permits the combined luminescence detection of two different reporter enzymes in the same tube, e.g., a dual assay for beta-galactosidase and luciferase. The sensitivity of these chemiluminescence assays

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19

Kawashima, Hidehisa, Nobuko Watanabe, Hisako K. Ijuin, and Masakatsu Matsumoto. "Magnesium methoxide-induced chemiluminescent decomposition of bicyclic dioxetanes bearing a 2′-alkoxy-2-hydroxy-1,1′-binaphthyl-7-yl moiety." Luminescence 28, no. 5 (2012): 696–704. http://dx.doi.org/10.1002/bio.2419.

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20

Wakasugi, Takeshi, Ken Fujimori, and Masakatsu Matsumoto. "Kinetics of Base Catalyzed Chemiluminescence Reaction of Spiro[adamantane -1,3′-(4′-(m-hydroxyphenyl)-4′-methoxy-1′,2′-dioxetane)]." Chemistry Letters 31, no. 7 (2002): 762–63. http://dx.doi.org/10.1246/cl.2002.762.

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21

Hoshiya, Naoyuki, Natsuki Fukuda, Hidetoshi Maeda, Nobuko Watanabe, and Masakatsu Matsumoto. "Synthesis and fluoride-induced chemiluminescent decomposition of bicyclic dioxetanes substituted with a 2-hydroxynaphthyl group." Tetrahedron 62, no. 24 (2006): 5808–20. http://dx.doi.org/10.1016/j.tet.2006.03.082.

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22

MATSUMOTO, M., N. WATANABE, H. KOBAYASHI, M. AZAMI, and H. IKAWA. "ChemInform Abstract: Synthesis and Chemiluminescence of 3,3-Diisopropyl-4-methoxy-4-(2- naphthyl)-1,2-dioxetanes." ChemInform 28, no. 20 (2010): no. http://dx.doi.org/10.1002/chin.199720048.

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23

Ciscato, Luiz Francisco M. L., Fernando H. Bartoloni, Aline S. Colavite, Dieter Weiss, Rainer Beckert, and Stefan Schramm. "Evidence supporting a 1,2-dioxetanone as an intermediate in the benzofuran-2(3H)-one chemiluminescence." Photochem. Photobiol. Sci. 13, no. 1 (2014): 32–37. http://dx.doi.org/10.1039/c3pp50345c.

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24

Watanabe, Nobuko, Ayu Wakatsuki, Hisako K. Ijuin, Yoshio Kabe, and Masakatsu Matsumoto. "Organic superbase-induced chemiluminescent decomposition of a hydroxyaryl-substituted dioxetane: Unique effect of a bifunctional guanidine base on the chemiluminescence profile of a bicyclic dioxetane bearing a 4-(benzoxazol-2-yl)-3,5-dihydroxyphenyl moiety." Tetrahedron Letters 59, no. 11 (2018): 971–77. http://dx.doi.org/10.1016/j.tetlet.2018.01.045.

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25

Lippold, Tim, Jörg M. Neudörfl, and Axel Griesbeck. "New Acridone- and (Thio)Xanthone-Derived 1,1-Donor–Acceptor-Substituted Alkenes: pH-Dependent Fluorescence and Unusual Photooxygenation Properties." Molecules 26, no. 11 (2021): 3305. http://dx.doi.org/10.3390/molecules26113305.

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A synthetic route to new heterocyclic 1,1-donor–acceptor-substituted alkenes starting with N-methyl-acridone, xanthone, and thioxanthone was investigated, leading to the acridone- and xanthone-derived products methyl 2-methoxy-2-(10-methylacridin-9 (10H)-ylidene)acetate (7) and methyl 2-methoxy-2-(9H-xanthen-9-ylidene)acetate (10) in low yields with the de-methoxylated product methyl 2-(10-methylacridin-9 (10H)-ylidene)acetate (8) and the reduced compound methyl 2-methoxy-2-(9H-xanthen-9-yl)acetate (11) as the major products from N-methyl acridone and xanthone. From thioxanthone, only the rear

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26

Chatzoudis, Apostolos, Vasileios Giannopoulos, Frank Hollmann, and Ioulia Smonou. "Surface-Doped Graphitic Carbon Nitride Catalyzed Photooxidation of Olefins and Dienes: Chemical Evidence for Electron Transfer and Singlet Oxygen Mechanisms." Catalysts 9, no. 8 (2019): 639. http://dx.doi.org/10.3390/catal9080639.

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A new photocatalytic reactivity of carbon-nanodot-doped graphitic carbon nitride (CD-C3N4) with alkenes and dienes, has been disclosed. We have shown that CD-C3N4 photosensitizes the oxidation of unsaturated substrates in a variety of solvents according to two competing mechanisms: the energy transfer via singlet oxygen (1O2) and/or the electron transfer via superoxide (O·−2). The singlet oxygen, derived by the CD-C3N4 photosensitized process, reacts with alkenes to form allylic hydroperoxides (ene products) whereas with dienes, endoperoxides. When the electron transfer mechanism operates, cle

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27

Graziano, M. Liliana, M. Rosaria Iesce, Guido Cimminiello, Rachele Scarpati, and Michelangelo Parrilli. "Dioxazole and dioxetane intermediates in the thermal rearrangement of endo-peroxides obtained by dye-sensitized photo-oxygenation of 2-alkoxyoxazoles." Journal of the Chemical Society, Perkin Transactions 1, no. 4 (1990): 1011. http://dx.doi.org/10.1039/p19900001011.

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28

Adam, Waldemar, and Markus Sauter. "Generation of 1,2-dioxetane decomposition products in the oxidation of 3-phenyl-2-methylbenzofuran epoxide by dimethyldioxirane and the oxodiperoxomoly." Tetrahedron 50, no. 28 (1994): 8393–98. http://dx.doi.org/10.1016/s0040-4020(01)85562-9.

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29

Adam, Waldemar, Elmar Kades та Xiaoheng Wang. "Photooxygenation of 3- and 2-silyloxybenzofurans: Rearrangement of dioxetanes via α-silylperoxy ketones to ketoester cleavage products". Tetrahedron Letters 31, № 16 (1990): 2259–62. http://dx.doi.org/10.1016/0040-4039(90)80200-6.

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30

Adam, Waldemar, and Simone Andler. "Thermolysis of 3,3-Bis(phenylmethyl)-1,2-dioxetane: Radical-Induced Formation of the Unusual Decomposition Product 3-Phenyl-1-(phenylmethoxy)-2-propanone." Journal of the American Chemical Society 116, no. 13 (1994): 5674–78. http://dx.doi.org/10.1021/ja00092a019.

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31

Adam, Waldemar, Sara G. Bosio, and Nicholas J. Turro. "Highly Diastereoselective Dioxetane Formation in the Photooxygenation of Enecarbamates with an Oxazolidinone Chiral Auxiliary: Steric Control in the [2 + 2] Cycloaddition of Singlet Oxygen through Conformational Alignment." Journal of the American Chemical Society 124, no. 30 (2002): 8814–15. http://dx.doi.org/10.1021/ja026815k.

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32

Watanabe, Nobuko, Hisako Kobayashi, Mitsunori Azami, and Masakatsu Matsumoto. "Synthesis of 3,3-diisopropyl-4-methoxy-4-(siloxy-2-naphthyl)-1,2-dioxetanes and their F−-induced chemiluminescent decomposition." Tetrahedron 55, no. 22 (1999): 6831–40. http://dx.doi.org/10.1016/s0040-4020(99)00336-1.

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33

Watanabe, Nobuko, Kumiko Nagamatsu, Toshiyuki Mizuno, and Masakatsu Matsumoto. "Bicyclic dioxetanes bearing an inden-2-yl or a benzo(b)thiazol-2-yl moiety as a CIEEL-active chemiluminescent substrate emitting red light." Luminescence 20, no. 2 (2005): 63–72. http://dx.doi.org/10.1002/bio.799.

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34

Martinez, Glaucia Regina, Hulyana Brum, Guilherme Lanzi Sassaki, et al. "Oxidation of 1-N2-etheno-2′-deoxyguanosine by singlet molecular oxygen results in 2′-deoxyguanosine: a pathway to remove exocyclic DNA damage?" Biological Chemistry 399, no. 8 (2018): 859–67. http://dx.doi.org/10.1515/hsz-2017-0337.

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Abstract Exocyclic DNA adducts are considered as potential tools for the study of oxidative stress-related diseases, but an important aspect is their chemical reactivity towards oxidant species. We report here the oxidation of 1-N2-etheno-2′-deoxyguanosine (1,N2-εdGuo) by singlet molecular oxygen (1O2) generated by a non-ionic water-soluble endoperoxide [N,N′-di(2,3-dihydroxypropyl)-1,4-naphthalenedipropanamide endoperoxide (DHPNO2)] and its corresponding oxygen isotopically labeled [18O]-[N,N′-di(2,3-dihydroxypropyl)-1,4- naphthalenedipropanamide endoperoxide (DHPN18O2)], and by photosensitiz

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35

Kopecky, Karl R., José Molina, and Rodrigo Rico. "Ozonolysis of tetramethoxyethene." Canadian Journal of Chemistry 66, no. 9 (1988): 2234–43. http://dx.doi.org/10.1139/v88-355.

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Ozonolysis of tetramethoxyethene 1 produces 20–40% of dimethyl carbonate 3, 35–60% of methyl trimethoxyacetate 7, and 20–35% of the dioxetane 8 of 1. Yields vary with initial concentration of 1, temperature, and solvent. Singlet oxygen is produced, which reacts with 1 to form 8 and can be trapped with 2,5-dimethylfuran. No evidence for the formation of the molozonide of 1 was obtained. Up to 2.5 moles of 1 are consumed per mole of ozone. Ozonolysis of a mixture of 1 and 2,3-dimethyl-2-butene 12 gave the epoxide of 12 and three times the expected amount of the allylic hydroperoxide of 12. A com

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36

Yu, Mohan, and Yajun Liu. "A QM/MM Study on the Initiation Reaction of Firefly Bioluminescence—Enzymatic Oxidation of Luciferin." Molecules 26, no. 14 (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 luc

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37

Adam, Waldemar, Sara G. Bosio, and Nicholas J. Turro. "ChemInform Abstract: Highly Diastereoselective Dioxetane Formation in the Photooxygenation of Enecarbamates with an Oxazolidinone Chiral Auxiliary: Steric Control in the [2 + 2] Cycloaddition of Singlet Oxygen Through Conformational Alignment." ChemInform 33, no. 46 (2010): no. http://dx.doi.org/10.1002/chin.200246134.

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38

Bogan, Denis J., and Dong Heon Lee. "Gas-phase chemiluminescence study of chemically activated tetramethyl-1,2-dioxetane formed from the reaction of oxygen (1.DELTA.g) with 2,3-dimethyl-2-butene." Journal of Physical Chemistry 96, no. 23 (1992): 9304–10. http://dx.doi.org/10.1021/j100202a046.

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39

Adam, Waldemar, Chantu R. Saha-Möller, and André Schönberger. "Type I and Type II Photosensitized Oxidative Modification of 2‘-Deoxyguanosine (dGuo) by Triplet-Excited Ketones Generated Thermally from the 1,2-Dioxetane HTMD." Journal of the American Chemical Society 119, no. 4 (1997): 719–23. http://dx.doi.org/10.1021/ja9629827.

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40

ADAM, W., and M. SAUTER. "ChemInform Abstract: Generation of 1,2-Dioxetane Decomposition Products in the Oxidation of 3-Phenyl-2-methylbenzofuran Epoxide by Dimethyldioxirane and the Oxodiperoxomolybdenum Complex." ChemInform 25, no. 49 (2010): no. http://dx.doi.org/10.1002/chin.199449099.

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41

ADAM, W., E. KADES та X. WANG. "ChemInform Abstract: Photooxygenation of 3- and 2-Silyloxybenzofurans: Rearrangement of Dioxetanes via α-Silylperoxy Ketones into Keto Ester Cleavage Products." ChemInform 22, № 5 (2010): no. http://dx.doi.org/10.1002/chin.199105117.

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42

Matsumoto, Masakatsu, Hisako Kobayashi, Jyunya Matsubara, et al. "Effect of allylic oxygen on the reaction pathways of singlet oxygenation: Selective formation of 1,2-dioxetanes from 1-alkoxymethyl-2-aryl-1-tert-butyl-2-methoxyethylenes." Tetrahedron Letters 37, no. 3 (1996): 397–400. http://dx.doi.org/10.1016/0040-4039(95)02185-x.

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43

Hoshiya, Naoyuki, Nobuko Watanabe, Hisako K. Ijuin, and Masakatsu Matsumoto. "Synthesis of bicyclic dioxetanes bearing a 2-hydroxy-1,1′-binaphthyl-5-yl moiety active toward intramolecular charge-transfer-induced chemiluminescent decomposition." Tetrahedron 62, no. 52 (2006): 12424–37. http://dx.doi.org/10.1016/j.tet.2006.09.108.

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44

Adam, Waldemar, Markus A. Arnold, Matthias Grüne, Werner M. Nau, Uwe Pischel, and Chantu R. Saha-Möller. "Spiroiminodihydantoin Is a Major Product in the Photooxidation of 2‘-Deoxyguanosine by the Triplet States and Oxyl Radicals Generated from Hydroxyacetophenone Photolysis and Dioxetane Thermolysis." Organic Letters 4, no. 4 (2002): 537–40. http://dx.doi.org/10.1021/ol017138m.

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45

Yoshimoto, Francis K., Eric Gonzalez, Richard J. Auchus та F. Peter Guengerich. "Mechanism of 17α,20-Lyase and New Hydroxylation Reactions of Human Cytochrome P450 17A1". Journal of Biological Chemistry 291, № 33 (2016): 17143–64. http://dx.doi.org/10.1074/jbc.m116.732966.

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Cytochrome P450 (P450) reactions can involve C–C bond cleavage, and several of these are critical in steroid and sterol biosynthesis. The mechanisms of P450s 11A1, 17A1, 19A1, and 51A1 have been controversial, in the context of the role of ferric peroxide (FeO2−) versus perferryl (FeO3+, compound I) chemistry. We reinvestigated the 17α-hydroxyprogesterone and 17α-hydroxypregnenolone 17α,20-lyase reactions of human P450 17A1 and found incorporation of one 18O atom (from 18O2) into acetic acid, consonant with proposals for a ferric peroxide mechanism (Akhtar, M., Lee-Robichaud, P., Akhtar, M. E.

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Natashin, Pavel V., Wei Ding, Elena V. Eremeeva, et al. "Structures of the Ca2+-regulated photoprotein obelin Y138F mutant before and after bioluminescence support the catalytic function of a water molecule in the reaction." Acta Crystallographica Section D Biological Crystallography 70, no. 3 (2014): 720–32. http://dx.doi.org/10.1107/s1399004713032434.

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Ca2+-regulated photoproteins, which are responsible for light emission in a variety of marine coelenterates, are a highly valuable tool for measuring Ca2+inside living cells. All of the photoproteins are a single-chain polypeptide to which a 2-hydroperoxycoelenterazine molecule is tightly but noncovalently bound. Bioluminescence results from the oxidative decarboxylation of 2-hydroperoxycoelenterazine, generating protein-bound coelenteramide in an excited state. Here, the crystal structures of the Y138F obelin mutant before and after bioluminescence are reported at 1.72 and 1.30 Å resolution,

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Tanimura, Masatoshi, Nobuko Watanabe, Hisako K. Ijuin, and Masakatsu Matsumoto. "Thermodynamic Aspects of Thermal Decomposition and Charge-Transfer-Induced Chemiluminescent Decomposition for Bicyclic Dioxetanes Bearing a 4-(Benzothiazol-2-yl)-3-hydroxyphenyl Moiety." Journal of Organic Chemistry 75, no. 11 (2010): 3678–84. http://dx.doi.org/10.1021/jo100449m.

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Tanimura, Masatoshi, Nobuko Watanabe, Hisako K. Ijuin, and Masakatsu Matsumoto. "Intramolecular Charge-Transfer-Induced Decomposition Promoted by an Aprotic Polar Solvent for Bicyclic Dioxetanes Bearing a 4-(Benzothiazol-2-yl)-3-hydroxyphenyl Moiety." Journal of Organic Chemistry 76, no. 3 (2011): 902–8. http://dx.doi.org/10.1021/jo1021822.

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Matsumoto, Masakatsu, Taichi Akimoto, Yuki Matsumoto, and Nobuko Watanabe. "Bicyclic dioxetanes bearing a 4-(benzoazol-2-yl)-3-hydroxyphenyl moiety: chemiluminescence profile for base-induced decomposition in aprotic medium and in aqueous medium." Tetrahedron Letters 46, no. 36 (2005): 6075–78. http://dx.doi.org/10.1016/j.tetlet.2005.07.008.

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Adam, Waldemar, Heinrich M. Harrer, and Alexander Treiber. "Synthesis of 1,4-Dioxa-2.lambda.5-phosphorinanes by Insertion of Triphenylalkylidenephosphoranes into the Peroxide Bond of 1,2-Dioxetanes: Thermolysis, Hydrolysis, and Wittig Olefination." Journal of the American Chemical Society 116, no. 17 (1994): 7581–87. http://dx.doi.org/10.1021/ja00096a015.

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