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Journal articles on the topic 'Ketoaldehyde'

Author: Grafiati

Published: 4 June 2021

Last updated: 4 February 2022

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1

Wolff, S. P., and R. T. Dean. "Glucose autoxidation and protein modification. The potential role of ‘autoxidative glycosylation’ in diabetes." Biochemical Journal 245, no. 1 (1987): 243–50. http://dx.doi.org/10.1042/bj2450243.

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Monosaccharide autoxidation (a transition metal-catalysed process that generates H2O2 and ketoaldehydes) appears to contribute to protein modification by glucose in vitro. The metal-chelating agent diethylenetriaminepenta-acetic acid (DETAPAC), which inhibits glucose autoxidation, also reduces the covalent attachment of glucose to bovine serum albumin. A maximal 45% inhibition of covalent attachment was observed, but this varied with glucose and DETAPAC concentrations in a complex fashion, suggesting at least two modes of attachment. The extent of inhibition of the metal-catalysed pathway corr

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2

Legge, Michael. "Oocyte and zygote ketoaldehyde utilisation." Biochimica et Biophysica Acta (BBA) - Molecular Cell Research 1355, no. 2 (1997): 99–101. http://dx.doi.org/10.1016/s0167-4889(96)00165-6.

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3

Moreno-Osorio, Luis, Manuel Cortés, Verónica Armstrong, María Bailén, and Azucena González-Coloma. "Antifeedant Activity of Some Polygodial Derivatives." Zeitschrift für Naturforschung C 63, no. 3-4 (2008): 215–20. http://dx.doi.org/10.1515/znc-2008-3-410.

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Polygodial (1) and its derivatives acetal 2 (propylene) and 3 (ethylene) were prepared and their antifeedant activity and toxic effects evaluated on several insect species with different feeding ecologies (Spodoptera littoralis, Leptinotarsa decemlineata, Myzus persicae and Rhopalosiphum padi) along with that of polygonone (4). We also tested their selective cytotoxic effects on insect-derived (Spodoptera frugiperda ovarian Sf9 cells) and mammalian Chinese hamster ovary (CHO) cells. The antifeedant activity of these compounds was consistent with the proposed mode of action for antifeedant drim

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4

Chen, Xin, Fajun Nan, Zhaoming Xiong, Sichang Shao, Tongshuang Li та Yulin li. "Synthesis and Allylic Oxidation of 2,3-Dehydro-9β-benzoyloxy-β-agarofuran". Collection of Czechoslovak Chemical Communications 60, № 3 (1995): 521–26. http://dx.doi.org/10.1135/cccc19950521.

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2,3-Dehydro-9β-benzoyloxy-β-agarofuran (VI), possible precursor of (+/-)-triptogelin G-2 (I), has been synthesized through a twelve-step procedure, allylic oxidation of which with various oxidative reagents has also been investigated, and three unusual oxidized products, ketoaldehyde X, peroxide XI, and ketone XII, were isolated.

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5

Kondratov, Ivan S., Igor I. Gerus, Marina V. Furmanova, Sergey I. Vdovenko та Valery P. Kukhar. "Reactions of ethyl triphenylphosphoranylideneacetate with fluorinated β-ketoaldehyde derivatives". Tetrahedron 63, № 30 (2007): 7246–55. http://dx.doi.org/10.1016/j.tet.2007.04.102.

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6

Nakajima, T., S. S. Davies, E. Matafonova та ін. "Selective γ-ketoaldehyde scavengers protect NaV1.5 from oxidant-induced inactivation". Journal of Molecular and Cellular Cardiology 48, № 2 (2010): 352–59. http://dx.doi.org/10.1016/j.yjmcc.2009.11.016.

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7

Xu, Guozhang, and Lawrence M. Sayre. "Structural Elucidation of a 2:2 4-Ketoaldehyde−Amine Adduct as a Model for Lysine-Directed Cross-Linking of Proteins by 4-Ketoaldehydes†." Chemical Research in Toxicology 12, no. 9 (1999): 862–68. http://dx.doi.org/10.1021/tx9900573.

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8

Hough, T. L., I. R. Hough та R. W. Pannell. "Synthesis and reactions of α-ketoaldehyde adducts of some heterocyclic ureas". Journal of Heterocyclic Chemistry 23, № 4 (1986): 1125–30. http://dx.doi.org/10.1002/jhet.5570230433.

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9

Liu, Jinbing, Fengyan Wu, Huacan Song, Zhihou Wang та Liangzhong Zhao. "Synthesis and antibacterial activities of para-alkoxy phenyl-β-ketoaldehyde derivatives". Medicinal Chemistry Research 22, № 9 (2013): 4228–38. http://dx.doi.org/10.1007/s00044-012-0429-8.

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10

Deslongchamps, Pierre, André Bélanger, Daniel J. F. Berney, et al. "The total synthesis of (+)-ryanodol. Part II. Model studies for rings B and C of (+)-anhydroryanodol. Preparation of a key pentacyclic intermediate." Canadian Journal of Chemistry 68, no. 1 (1990): 127–52. http://dx.doi.org/10.1139/v90-022.

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This paper reports several model studies that were necessary for the rational conception of a simple four-step synthesis (6 + (S)-74 → 81a–b → 83 [Formula: see text] 87 → 89) (Scheme 11) of the carbonate derivative 89 of the optically active pentacyclic dihydroxy ketoaldehyde 87, an important key intermediate for the synthesis of (+)-ryanodol (5). The optically active vinyl ketone (S)-74 that was used as starting material was prepared in four steps from d-carvone ((S)-94) (Scheme 13). The preparation of the other starting material, the o-spirolactone dienone 6, was reported in Part I. Keywords

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11

Umarov, Bako Bafoevich, Murod Amonovich Tursunov, and Mansur Yarashovich Ergashov. "2,4-STUD 2,4-STUDY OF THE STRUC Y OF THE STRUCTURE OF THE P TURE OF THE PAIR EXCHANGE DERIVATIVES E TIVES ETHYL ESTER DIO YL ESTER DIOXOPENTANOATE ACID BY THE METHOD OF PMR AND SAR." Scientific Reports of Bukhara State University 4, no. 2 (2020): 3–8. http://dx.doi.org/10.52297/2181-1466/2020/4/2/7.

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Analysis of the scientific literature shows that data on nitrogenous derivatives of ketoaldehyde and ketoesters, their synthesis, tautomerization and Complexing ability are incomplete, in some cases their coordination compounds remain abstract, which requires special attention. As a result of the study of the electronic and spatial structures of the complex molecules, it became possible to determine the causes of the "composition-structure-properties" relationship of chemical compounds in a much more complex structure. The structure and tautomerization of para-exchange acylgases of ethyl ether

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12

Ahlbrecht, Hubertus, and Axel Von Daacke. "1,4-Ketoaldehyde durch Michael-Addition deprotonierter Aldimine an 2-(N-Methylanilino)-acrylonitril." Synthesis 1987, no. 01 (1987): 24–28. http://dx.doi.org/10.1055/s-1987-27829.

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13

Jäger, Ernst-G., Dietrich Seidel та Wolfgang Schade. "Azine aliphatischer β-Ketoaldehyde als Liganden in einem neuen Typ planarer Zweikernkomplexe". Zeitschrift für Chemie 22, № 8 (2010): 302–3. http://dx.doi.org/10.1002/zfch.19820220807.

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14

Hunt, J. V., R. T. Dean, and S. P. Wolff. "Hydroxyl radical production and autoxidative glycosylation. Glucose autoxidation as the cause of protein damage in the experimental glycation model of diabetes mellitus and ageing." Biochemical Journal 256, no. 1 (1988): 205–12. http://dx.doi.org/10.1042/bj2560205.

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Protein exposed to glucose is cleaved, undergoes conformational change and develops fluorescent adducts (‘glycofluorophores’). These changes are presumed to result from the covalent attachment of glucose to amino groups. We have demonstrated, however, that the fragmentation and conformational changes observed are dependent upon hydroxyl radicals produced by glucose autoxidation, or some closely related process, and that antioxidants dissociate structural damage caused by the exposure of glucose to protein from the incorporation of monosaccharide into protein. We have also provided further evid

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15

Davies, Sean S., Chris Bodine, Elena Matafonova та ін. "Treatment with a γ-Ketoaldehyde Scavenger Prevents Working Memory Deficits in hApoE4 Mice". Journal of Alzheimer's Disease 27, № 1 (2011): 49–59. http://dx.doi.org/10.3233/jad-2011-102118.

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16

Guo, Lilu, Zhongyi Chen, Brian E. Cox та ін. "Phosphatidylethanolamines Modified by γ-Ketoaldehyde (γKA) Induce Endoplasmic Reticulum Stress and Endothelial Activation". Journal of Biological Chemistry 286, № 20 (2011): 18170–80. http://dx.doi.org/10.1074/jbc.m110.213470.

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17

Roychowdhury, Sanjoy, Megan R. McMullen, Michele T. Pritchard, Wei Li, Robert G. Salomon та Laura E. Nagy. "Formation of γ-ketoaldehyde–protein adducts during ethanol-induced liver injury in mice". Free Radical Biology and Medicine 47, № 11 (2009): 1526–38. http://dx.doi.org/10.1016/j.freeradbiomed.2009.07.015.

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18

Yamada, Takeshi, Yuki Mizutani, Yoshihide Umebayashi, et al. "Tandyukisin, a novel ketoaldehyde decalin derivative, produced by a marine sponge-derived Trichoderma harzianum." Tetrahedron Letters 55, no. 3 (2014): 662–64. http://dx.doi.org/10.1016/j.tetlet.2013.11.107.

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19

Beye, Garrison E., Athanasios Karagiannis, Alieh Kazemeini та Dale E. Ward. "A versatile method for the synthesis of γ-pyrones". Canadian Journal of Chemistry 90, № 11 (2012): 954–64. http://dx.doi.org/10.1139/v2012-067.

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A versatile three-step procedure to annulate a γ-pyrone onto a methylene ketone was developed involving (i) aldol reaction with a dithiolane-protected β-ketoaldehyde, (ii) oxidation of the aldol adduct to a β-diketone, and (iii) treatment of the resulting dithiolane-protected 1,3,5-trione with 2-iodoxybenzoic acid (IBX) and trifluoromethanesulfonic acid (triflic acid; TfOH) in acetonitrile at ambient temperature to give the corresponding γ-pyrone. Cyclization proceeded with IBX alone, but significantly improved yields were obtained with added acid, particularly triflic acid. A dithiolane was m

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20

Faggin, Patrizia, Anna Maria Bassi, Renata Finollo, and Giovanni Brambilla. "Induction of sister-chromatid exchanges in Chinese hamster ovary cells by the biotic ketoaldehyde methylglyoxal." Mutation Research Letters 144, no. 3 (1985): 189–91. http://dx.doi.org/10.1016/0165-7992(85)90138-1.

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21

Yamada, Takeshi, Yuki Mizutani, Yoshihide Umebayashi, et al. "ChemInform Abstract: Tandyukisin, a Novel Ketoaldehyde Decalin Derivative, Produced by a Marine Sponge-Derived Trichoderma harzianum." ChemInform 45, no. 25 (2014): no. http://dx.doi.org/10.1002/chin.201425219.

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22

Takao, Ken-ichi, Seigo Nagata, Susumu Kobayashi, Hisanaka Ito та Takeo Taguchi. "Model Study for the Total Synthesis of Antifungal Australifungin: Construction of α-Diketone and β-Ketoaldehyde Moieties". Chemistry Letters 27, № 5 (1998): 447–48. http://dx.doi.org/10.1246/cl.1998.447.

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23

Uenishi, Jun'ichi, Souichiro Masuda та Shoji Wakabayashi. "Intramolecular Sm2+ and Sm3+ promoted reaction of γ-oxy-δ-ketoaldehyde; stereocontrolled formation of pinacol and lactone". Tetrahedron Letters 32, № 38 (1991): 5097–100. http://dx.doi.org/10.1016/s0040-4039(00)93437-3.

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24

Salem, Nahed M. H., Amal R. Rashad, Laila El Sayed, W. Haase та Magdi F. Iskander. "Synthesis, characterization, molecular and supramolecular structures of nickel(II) complexes derived from α-diketone and α-ketoaldehyde bisaroylhydrazones". Polyhedron 28, № 11 (2009): 2137–48. http://dx.doi.org/10.1016/j.poly.2009.04.007.

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25

Zagol-Ikapitte, Irene, Elena Matafonova, Venkataraman Amarnath та ін. "Determination of the Pharmacokinetics and Oral Bioavailability of Salicylamine, a Potent γ-Ketoaldehyde Scavenger, by LC/MS/MS". Pharmaceutics 2, № 1 (2010): 18–29. http://dx.doi.org/10.3390/pharmaceutics2010018.

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26

Oimomi, M., F. Hata, N. Igaki, T. Nakamichi, S. Baba та H. Kato. "Purification of α-ketoaldehyde dehydrogenase from the human liver and its possible significance in the control of glycation". Experientia 45, № 5 (1989): 463–66. http://dx.doi.org/10.1007/bf01952031.

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27

TAKAO, K., S. NAGATA, S. KOBAYASHI, H. ITO та T. TAGUCHI. "ChemInform Abstract: Model Study for the Total Synthesis of Antifungal Australifungin: Construction of α-Diketone and β-Ketoaldehyde Moieties." ChemInform 29, № 39 (2010): no. http://dx.doi.org/10.1002/chin.199839283.

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28

Suttisansanee, Uthaiwan, and John F. Honek. "Preliminary Characterization of a Ni2+-Activated and Mycothiol-Dependent Glyoxalase I Enzyme from Streptomyces coelicolor." Inorganics 7, no. 8 (2019): 99. http://dx.doi.org/10.3390/inorganics7080099.

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The glyoxalase system consists of two enzymes, glyoxalase I (Glo1) and glyoxalase II (Glo2), and converts a hemithioacetal substrate formed between a cytotoxic alpha-ketoaldehyde, such as methylglyoxal (MG), and an intracellular thiol, such as glutathione, to a non-toxic alpha-hydroxy acid, such as d-lactate, and the regenerated thiol. Two classes of Glo1 have been identified. The first is a Zn2+-activated class and is exemplified by the Homo sapiens Glo1. The second class is a Ni2+-activated enzyme and is exemplified by the Escherichia coli Glo1. Glutathione is the intracellular thiol employe

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29

Yang, Jian, Fuming Mei, Shitao Fu та Yanlong Gu. "Facile synthesis of 1,4-diketones via three-component reactions of α-ketoaldehyde, 1,3-dicarbonyl compound, and a nucleophile in water". Green Chemistry 20, № 6 (2018): 1367–74. http://dx.doi.org/10.1039/c7gc03644b.

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Three-component reactions of alkylglyoxals, 1,3-dicarbonyl compounds, and a nucleophile were performed under aqueous and catalyst-free conditions, which produced 1,4-diketone scaffolds in a straightforward way.

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30

Nguyen, Thuy T., Joshua P. Fessel, Samuel W. Caito, James D. West, Michael Aschner, and L. Jackson Roberts, II. "Reactive y-Ketoaldehyde Scavengers Extend Lifespan and Healthspan in C. Elegans through Protein-Level Interactions with Sir2.1 and Ets-7." Free Radical Biology and Medicine 87 (October 2015): S131. http://dx.doi.org/10.1016/j.freeradbiomed.2015.10.342.

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31

Sakai, Atsushi, Toyohiko Aoyama та Takayuki Shioiri. "An efficient synthesis of 2-cyclopentenones from γ-ketoaldehyde acetals using lithium trimethylsilyldiazomethane. Its application to the synthesis of trichodenone C". Tetrahedron Letters 41, № 35 (2000): 6859–63. http://dx.doi.org/10.1016/s0040-4039(00)01162-x.

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32

Bi, Wenzhao, Geeng-Fu Jang, Lei Zhang, et al. "The Adductomics of Isolevuglandins: Oxidation of IsoLG Pyrrole Intermediates Generates Pyrrole–Pyrrole Crosslinks and Lactams." High-Throughput 8, no. 2 (2019): 12. http://dx.doi.org/10.3390/ht8020012.

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Isoprostane endoperoxides generated by free radical-induced oxidation of arachidonates, and prostaglandin endoperoxides generated through enzymatic cyclooxygenation of arachidonate, rearrange nonenzymatically to isoprostanes and a family of stereo and structurally isomeric γ-ketoaldehyde seco-isoprostanes, collectively known as isolevuglandins (isoLGs). IsoLGs are stealthy toxins, and free isoLGs are not detected in vivo. Rather, covalent adducts are found to incorporate lysyl ε-amino residues of proteins or ethanolamino residues of phospholipids. In vitro studies have revealed that adduction

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33

Davies, Sean S., Venkataraman Amarnath, Cynthia J. Brame, Olivier Boutaud та L. Jackson Roberts. "Measurement of chronic oxidative and inflammatory stress by quantification of isoketal/levuglandin γ-ketoaldehyde protein adducts using liquid chromatography tandem mass spectrometry". Nature Protocols 2, № 9 (2007): 2079–91. http://dx.doi.org/10.1038/nprot.2007.298.

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34

Xia, Qi, Xiang Li, Xi Fu та ін. "Copper-Catalyzed Three-Component Reactions of α-Ketoaldehyde, 1,3-Dicarbonyl Compound, and Organic Boronic Acid in Water: A Route to 1,4-Diketones". Journal of Organic Chemistry 86, № 14 (2021): 9914–23. http://dx.doi.org/10.1021/acs.joc.1c01100.

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35

Sakai, Atsushi, Toyohiko Aoyama та Takayuki Shioiri. "ChemInform Abstract: An Efficient Synthesis of 2-Cyclopentenones from γ-Ketoaldehyde Acetals Using Lithium Trimethylsilyldiazomethane. Its Application to the Synthesis of Trichodenone C (XXI)." ChemInform 31, № 50 (2000): no. http://dx.doi.org/10.1002/chin.200050076.

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36

Siebert, Hans-Christian, Emad Tajkhorshid, and Janusz Dabrowski. "Barrier to Rotation around the Csp2-Csp2Bond of the Ketoaldehyde Enol Ether MeC(O)CHCH−OEt As Determined by13C NMR and ab Initio Calculations." Journal of Physical Chemistry A 105, no. 37 (2001): 8488–94. http://dx.doi.org/10.1021/jp004476g.

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37

Prakash, Om, Rajesh Kumar, Deepak Sharma, Kamaljeet Pannu та Raj Kamal. "The Chemistry of α,β-Ditosyloxyketones: Novel Routes for the Synthesis of Desoxybenzoins and α-Aryl-β-ketoaldehyde Dimethylacetals from α,β-Chalcone Ditosylates". Synlett 2007, № 14 (2007): 2189–92. http://dx.doi.org/10.1055/s-2007-984915.

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38

Roscales, S., та A. G. Csákÿ. "Transition-metal free reactions of boronic acids: cascade addition – ring-opening of furans towards functionalized γ-ketoaldehydes". Chemical Communications 52, № 14 (2016): 3018–21. http://dx.doi.org/10.1039/c5cc08809g.

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39

Ni, Meiyan, Jianguo Zhang, Xiaoyu Liang, Yaojia Jiang, and Teck-Peng Loh. "Directed C–C bond cleavage of a cyclopropane intermediate generated fromN-tosylhydrazones and stable enaminones: expedient synthesis of functionalized 1,4-ketoaldehydes." Chemical Communications 53, no. 91 (2017): 12286–89. http://dx.doi.org/10.1039/c7cc07178g.

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40

Venkateswarlu, Vunnam, K. A. Aravinda Kumar, Sorav Gupta, Deepika Singh, Ram A. Vishwakarma та Sanghapal D. Sawant. "DMSO/I2 mediated C–C bond cleavage of α-ketoaldehydes followed by C–O bond formation: a metal-free approach for one-pot esterification". Organic & Biomolecular Chemistry 13, № 29 (2015): 7973–78. http://dx.doi.org/10.1039/c5ob01015b.

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41

Guguloth, Veeranna, Ramesh Balaboina, Narasimha Swamy Thirukovela, and Ravinder Vadde. "One-pot synthesis of 3-aminofurans using a simple and efficient recyclable CuI/[bmim]PF6 system." Organic & Biomolecular Chemistry 19, no. 34 (2021): 7438–45. http://dx.doi.org/10.1039/d1ob01132d.

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42

Kumar, Indresh, Nisar A. Mir, Panduga Ramaraju, Deepika Singh, Vivek K. Gupta, and Rajnikant Rajnikant. "Direct catalytic synthesis of densely substituted 3-formylpyrroles from imines and 1,4-ketoaldehydes." RSC Adv. 4, no. 65 (2014): 34548–51. http://dx.doi.org/10.1039/c4ra06581f.

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An organocatalytic formal [3 + 2] cycloaddition have been developed between 1,4-ketoaldehydes and imines to synthesize densely substituted 3-formylpyrroles in high yields (up to 70%) under mild conditions at room temperature.

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43

Feliciano, Arturo San, Esther Caballero, Juan A. P. Pereira та Pilar Puebla. "Pyrrole derivatives from α-ketoaldehydes". Tetrahedron 45, № 20 (1989): 6553–62. http://dx.doi.org/10.1016/s0040-4020(01)89532-6.

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44

Zagol-Ikapite, Irene, Iberia Romina Sosa, Audra M. Judd, Olivier Boutaud, and John A. Oates. "Quantification Of Malondialdehyde Adducts In Platelet Activation As An Indicator Of Proinflammatory and Prothombotic State." Blood 122, no. 21 (2013): 4735. http://dx.doi.org/10.1182/blood.v122.21.4735.4735.

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Background The formation of malondialdehyde (MDA) has been previously described as a product of the thromboxane synthase. However, the reported approaches for its quantification have not been reliable, stymieing its use in research. As a reactive di-carbonyl, MDA reacts with primary amines, notably lysines on proteins, to form covalent adducts of several types. Three of the products of the reaction of MDA with lysine are an N-propenal adduct, a dihydropyridine ring adduct (N-lysyl-4-methyl-2, 6-dihydropyridine-3, 5-dicarbaldehyde), and a lysyl-MDA crosslink. Measurement of platelet protein mod

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45

Honek, John F. "Glyoxalase biochemistry." Biomolecular Concepts 6, no. 5-6 (2015): 401–14. http://dx.doi.org/10.1515/bmc-2015-0025.

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AbstractThe glyoxalase enzyme system utilizes intracellular thiols such as glutathione to convert α-ketoaldehydes, such as methylglyoxal, into D-hydroxyacids. This overview discusses several main aspects of the glyoxalase system and its likely function in the cell. The control of methylglyoxal levels in the cell is an important biochemical imperative and high levels have been associated with major medical symptoms that relate to this metabolite’s capability to covalently modify proteins, lipids and nucleic acid.

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46

Chen, Weijie, та Daniel Seidel. "Redox-Annulation of Cyclic Amines and β-Ketoaldehydes". Organic Letters 18, № 5 (2016): 1024–27. http://dx.doi.org/10.1021/acs.orglett.6b00151.

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47

Nguyen, Tran B., Alexander Laskin, Julia Laskin, and Sergey A. Nizkorodov. "Brown carbon formation from ketoaldehydes of biogenic monoterpenes." Faraday Discussions 165 (2013): 473. http://dx.doi.org/10.1039/c3fd00036b.

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48

Kochergin, P. M., L. S. Blinova, and G. A. Karpov. "Synthesis of ketones, ketoaldehydes, and ketoacids from nitroesters." Pharmaceutical Chemistry Journal 28, no. 4 (1994): 271–73. http://dx.doi.org/10.1007/bf02219801.

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49

Quiclet-Sire, Béatrice, and Samir Zard. "Convergent Routes to Pyrroles Exploiting the Unusual Radical Chemistry of Xanthates – An Overview." Synlett 28, no. 20 (2017): 2685–96. http://dx.doi.org/10.1055/s-0036-1590809.

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Convergent routes to a variety of pyrroles involving radical additions of xanthates are described. Emphasis is placed on reactions leading to the formation of 1,4-diketones or 1,4-ketoaldehydes or their synthetic equivalents, which can then be condensed with ammonia or primary amines in a variation of the classical Paal–Knorr synthesis of pyrroles. The modification of pyrroles by direct radical addition is also discussed.1 Introduction2 Earlier Routes to Pyrroles3 The Xanthate Radical Addition–Transfer Process4 Application to Pyrrole Synthesis5 Further Variations6 Direct Modification of Existi

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50

Davies, Sean S., Nathalie Bernoud-Hubac, Sandra Olsen, Thomas J. Montine та L. Jackson Roberts. "P4-229 Highly reactive γ-ketoaldehydes in Alzheimer's disease". Neurobiology of Aging 25 (липень 2004): S540. http://dx.doi.org/10.1016/s0197-4580(04)81787-1.

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