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Journal articles on the topic 'Sulfenic acid'

Author: Grafiati

Published: 4 June 2021

Last updated: 12 February 2022

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1

Yoshimura, Toshiaki, Eiichi Tsukurimichi, Satoru Yamazaki, Shinichi Soga, Choichiro Shimasaki, and Kiyoshi Hasegawa. "Synthesis of a stable sulfenic acid, trans-decalin-9-sulfenic acid." Journal of the Chemical Society, Chemical Communications, no. 18 (1992): 1337. http://dx.doi.org/10.1039/c39920001337.

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2

Gupta, Vinayak, and Kate S. Carroll. "Rational design of reversible and irreversible cysteine sulfenic acid-targeted linear C-nucleophiles." Chemical Communications 52, no. 16 (2016): 3414–17. http://dx.doi.org/10.1039/c6cc00228e.

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We report the design of linear C-nucleophiles that react with sulfenic acid in a covalent, reversible manner. We further establish that linear C-nucleophile moieties present in the rheumatoid arthritis drug, tofacitinib and natural product, curcumin also form covalent adducts with sulfenic acid.

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3

Tripolt, Robert, Ferdinand Belaj, and Edgar Nachbaur. "Eine unerwartet stabile Sulfensäure: 4,6-Dimethoxy-1,3,5-triazin-2-sulfensäure; Synthese, Eigenschaften, Molekül- und Kristallstruktur / Unexpectedly Stable Sulfenic Acid: 4,6-Dimethoxy-1,3,5-triazine-2-sulfenic Acid; Synthesis, Properties, Molecular and Crystal Structure." Zeitschrift für Naturforschung B 48, no. 9 (1993): 1212–22. http://dx.doi.org/10.1515/znb-1993-0909.

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4,6-Dimethoxy-1,3,5-triazine-2-sulfenic acid (1) was prepared by the reaction of 4,6-dimethoxy-1,3,5-triazine-2(1H)-thion (3) with 2-benzenesulfonyl-3-(p-nitrophenyl)-oxaziridine (2) in THF solution and isolated as a stable crystalline solid. The new compound was characterized by analytical and spectroscopic data (IR, 1H and 13C NMR, UV, MS) supported by MNDO-PM 3 calculations. UV spectrometry was used for exact determination of the ionization constant of 1(pKa = 5.86 ± 0.02 at 20°C). According to 13C NMR data and X-ray analysis the sulfenic acid 1 adopts the sulfenyl structure (R—SOH) in the

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4

Sano, Tsukasa, Ryosuke Masuda, Shohei Sase, and Kei Goto. "Isolable small-molecule cysteine sulfenic acid." Chemical Communications 57, no. 20 (2021): 2479–82. http://dx.doi.org/10.1039/d0cc08422k.

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A small-molecule cysteine sulfenic acid (Cys–SOH) with ‘shelf stability’ protected by a molecular cradle was synthesized by direct oxidation of a thiol with H<sub>2</sub>O<sub>2</sub>. Its crystal structure and biologically relevant reactivity were elucidated.

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5

Tureček, František, Libor Brabec, Tomáš Vondrák, Vladimír Hanuš, Josef Hájíček, and Zdeněk Havlas. "Sulfenic acids in the gas phase. Preparation, ionization energies and heats of formation of methane-, ethene-, and benzenesulfenic acid." Collection of Czechoslovak Chemical Communications 53, no. 9 (1988): 2140–58. http://dx.doi.org/10.1135/cccc19882140.

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Methane-, ethene-, and ethynesulfenic acids were generated in the gas phase by flash-vacuum pyrolysis of the corresponding tert-butyl sulfoxides at 400 °C and 10-4 Pa. Benzenesulfenic acid was prepared from phenyl 3-buten-1-yl sulfoxide at 350 °C and 10-4 Pa. The sulfenic acids were characterized by mass spectrometry Threshold ionization energies (IE) were measured as IE(CH3SOH) = 9·07 ± 0·03 eV, IE(CH2=CHSOH) = 8·70 ± 0·03 eV, IE(HCCSOH) = 8·86 ± 0·04 eV, and IE(C6H5SOH) = 8·45 + 0·03 eV. Radical cations [CH3SOH].+, [CH2=CHSOH].+, and [HCCSOH].+ were generated by electron-impact-induced loss

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6

Chipiso, Kudzanai, and Reuben H. Simoyi. "Kinetics and Mechanism of Oxidation of d-Penicillamine in Acidified Bromate and Aqueous Bromine." Australian Journal of Chemistry 69, no. 11 (2016): 1305. http://dx.doi.org/10.1071/ch16050.

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The oxidation of the biologically active compound d-penicillamine (Depen) by acidic bromate has been studied. The stoichiometry of the reaction is strictly 1 : 1, in which Depen is oxidized only as far as the sulfonic acid with no cleavage of the C–S bond to yield sulfate. Electrospray ionization spectroscopy shows that Depen is oxidized through addition of oxygen atoms on the sulfur centre to successively yield sulfenic and sulfinic acids before the product sulfonic acid. In conditions of excess Depen over the oxidant, sulfenic acid was not observed. Instead, nearly quantitative formation of

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7

Schwan, Adrian L., and Stefan C. Söderman. "Discoveries in Sulfenic Acid Anion Chemistry." Phosphorus, Sulfur, and Silicon and the Related Elements 188, no. 4 (2013): 275–86. http://dx.doi.org/10.1080/10426507.2012.729116.

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8

Carballal, S., B. Alvarez, L. Turell, H. Botti, B. A. Freeman, and R. Radi. "Sulfenic acid in human serum albumin." Amino Acids 32, no. 4 (2006): 543–51. http://dx.doi.org/10.1007/s00726-006-0430-y.

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9

Freeman, Fillmore. "Mechanism of the cysteine sulfenic acid O-sulfenylation of 1,3-cyclohexanedione." Chem. Commun. 50, no. 31 (2014): 4102–4. http://dx.doi.org/10.1039/c4cc00925h.

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10

Barattucci, Anna, Tania M. G. Salerno, Franz H. Kohnke, Teresa Papalia, Fausto Puntoriero, and Paola Bonaccorsi. "Curcumin-based sulfenic acid as a light switch for the binding of biothiols." New Journal of Chemistry 44, no. 45 (2020): 19508–14. http://dx.doi.org/10.1039/d0nj04834h.

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11

Liu, C. Tony, and Stephen J. Benkovic. "Capturing a Sulfenic Acid with Arylboronic Acids and Benzoxaborole." Journal of the American Chemical Society 135, no. 39 (2013): 14544–47. http://dx.doi.org/10.1021/ja407628a.

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12

Adhikari, Sarju, Ramon Crehuet, Josep M. Anglada, Joseph S. Francisco, and Yu Xia. "Two-step reaction mechanism reveals new antioxidant capability of cysteine disulfides against hydroxyl radical attack." Proceedings of the National Academy of Sciences 117, no. 31 (2020): 18216–23. http://dx.doi.org/10.1073/pnas.2006639117.

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Cysteine disulfides, which constitute an important component in biological redox buffer systems, are highly reactive toward the hydroxyl radical (•OH). The mechanistic details of this reaction, however, remain unclear, largely due to the difficulty in characterizing unstable reaction products. Herein, we have developed a combined approach involving mass spectrometry (MS) and theoretical calculations to investigate reactions of•OH with cysteine disulfides (Cys–S–S–R) in the gas phase. Four types of first-generation products were identified: protonated ions of the cysteine thiyl radical (+Cys–S•

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13

Makarov, Sergei V., Attila K. Horváth, and Anna S. Makarova. "Reactivity of Small Oxoacids of Sulfur." Molecules 24, no. 15 (2019): 2768. http://dx.doi.org/10.3390/molecules24152768.

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Oxidation of sulfide to sulfate is known to consist of several steps. Key intermediates in this process are the so-called small oxoacids of sulfur (SOS)—sulfenic HSOH (hydrogen thioperoxide, oxadisulfane, or sulfur hydride hydroxide) and sulfoxylic S(OH)2 acids. Sulfur monoxide can be considered as a dehydrated form of sulfoxylic acid. Although all of these species play an important role in atmospheric chemistry and in organic synthesis, and are also invoked in biochemical processes, they are quite unstable compounds so much so that their physical and chemical properties are still subject to i

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14

Barrett, Tessa J., David I. Pattison, Stephen E. Leonard, Kate S. Carroll, Michael J. Davies, and Clare L. Hawkins. "Inactivation of thiol-dependent enzymes by hypothiocyanous acid: role of sulfenyl thiocyanate and sulfenic acid intermediates." Free Radical Biology and Medicine 52, no. 6 (2012): 1075–85. http://dx.doi.org/10.1016/j.freeradbiomed.2011.12.024.

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15

Zyk, N. V., A. Yu Gavrilova, O. A. Mukhina, O. B. Bondarenko, and N. S. Zefirov. "Sulfenic acid esters as promising sulfenylating agents." Russian Journal of Organic Chemistry 42, no. 12 (2006): 1856–57. http://dx.doi.org/10.1134/s1070428006120177.

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16

Gupta, Vinayak, and Kate S. Carroll. "Sulfenic acid chemistry, detection and cellular lifetime." Biochimica et Biophysica Acta (BBA) - General Subjects 1840, no. 2 (2014): 847–75. http://dx.doi.org/10.1016/j.bbagen.2013.05.040.

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17

Sharar, M., Humberto Rodríguez-Solla, M. W. Linscheid, and Maria Montes-Bayón. "Detection of sulfenic acid in intact proteins by mass spectrometric techniques: application to serum samples." RSC Adv. 7, no. 70 (2017): 44162–68. http://dx.doi.org/10.1039/c7ra06241a.

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18

Kumar, Murugaeson R., and Patrick J. Farmer. "Characterization of Polysulfides, Polysulfanes, and Other Unique Species in the Reaction between GSNO and H2S." Molecules 24, no. 17 (2019): 3090. http://dx.doi.org/10.3390/molecules24173090.

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Glutathione-based products, GSnX, of the reaction of hydrogen sulfide, H2S, S-nitroso glutathione, and GSNO, at varied stoichiometries have been analyzed by liquid chromatography high-resolution mass spectrometry (LC-HRMS) and chemical trapping experiments. A wide variety of glutathione-based species with catenated sulfur chains have been identified including sulfanes (GSSnG), sulfides (GSSnH), and sulfenic acids (GSnOH); sulfinic (GSnO2H) and sulfonic (GSnO3H) acids are also seen in reactions exposed to air. The presence of each species of GSnX within the original reaction mixtures was confir

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19

TRIPOLT, R., F. BELAJ, and E. NACHBAUR. "ChemInform Abstract: Unexpectedly Stable Sulfenic Acid: 4,6-Dimethoxy-1,3,5-triazine-2- sulfenic Acid; Synthesis, Properties, Molecular and Crystal Structure." ChemInform 25, no. 1 (2010): no. http://dx.doi.org/10.1002/chin.199401231.

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20

Volbeda, Anne, Lydie Martin, Pierre-Pol Liebgott, Antonio L. De Lacey, and Juan C. Fontecilla-Camps. "[NiFe]-hydrogenases revisited: nickel–carboxamido bond formation in a variant with accrued O2-tolerance and a tentative re-interpretation of Ni-SI states." Metallomics 7, no. 4 (2015): 710–18. http://dx.doi.org/10.1039/c4mt00309h.

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21

Lourenço dos Santos, Sofia, Isabelle Petropoulos, and Bertrand Friguet. "The Oxidized Protein Repair Enzymes Methionine Sulfoxide Reductases and Their Roles in Protecting against Oxidative Stress, in Ageing and in Regulating Protein Function." Antioxidants 7, no. 12 (2018): 191. http://dx.doi.org/10.3390/antiox7120191.

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Cysteine and methionine residues are the amino acids most sensitive to oxidation by reactive oxygen species. However, in contrast to other amino acids, certain cysteine and methionine oxidation products can be reduced within proteins by dedicated enzymatic repair systems. Oxidation of cysteine first results in either the formation of a disulfide bridge or a sulfenic acid. Sulfenic acid can be converted to disulfide or sulfenamide or further oxidized to sulfinic acid. Disulfide can be easily reversed by different enzymatic systems such as the thioredoxin/thioredoxin reductase and the glutaredox

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22

Gupta, Vinayak, and Kate S. Carroll. "Profiling the reactivity of cyclic C-nucleophiles towards electrophilic sulfur in cysteine sulfenic acid." Chemical Science 7, no. 1 (2016): 400–415. http://dx.doi.org/10.1039/c5sc02569a.

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Oxidation of a protein cysteine thiol to sulfenic acid, termed S-sulfenylation, is a reversible post-translational modification that plays a crucial role in regulating protein function and is correlated with disease states.

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23

Turell, Lucía, Horacio Botti, Sebastián Carballal, et al. "Reactivity of Sulfenic Acid in Human Serum Albumin†." Biochemistry 47, no. 1 (2008): 358–67. http://dx.doi.org/10.1021/bi701520y.

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24

O'donnell, Jennifer S., and Adrian L. Schwan. "Generation, structure and reactions of sulfenic acid anions." Journal of Sulfur Chemistry 25, no. 2-3 (2004): 183–211. http://dx.doi.org/10.1080/1741599042000220761.

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25

Poole, Thomas H., Julie A. Reisz, Weiling Zhao, Leslie B. Poole, Cristina M. Furdui, and S. Bruce King. "Strained Cycloalkynes as New Protein Sulfenic Acid Traps." Journal of the American Chemical Society 136, no. 17 (2014): 6167–70. http://dx.doi.org/10.1021/ja500364r.

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26

Ishii, Akihiko, Ken Komiya, and Juzo Nakayama. "Synthesis and Characterization of Thiophenetriptycene-8-sulfenic Acid." Phosphorus, Sulfur, and Silicon and the Related Elements 120, no. 1 (1997): 323–24. http://dx.doi.org/10.1080/10426509708043962.

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27

Ishii, Akihiko, Ken Komiya, and Juzo Nakayama. "Synthesis and Characterization of Thiophenetriptyeene-8-sulfenic Acid." Phosphorus, Sulfur, and Silicon and the Related Elements 120, no. 1 (1997): 323–24. http://dx.doi.org/10.1080/10426509708545530.

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28

Ding, Jianan, Qiulian Mao, Meng Zhao, et al. "Protein sulfenic acid-mediated anchoring of gold nanoparticles for enhanced CT imaging and radiotherapy of tumors in vivo." Nanoscale 12, no. 45 (2020): 22963–69. http://dx.doi.org/10.1039/d0nr06440h.

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Herein, smart protein sulfenic acid-reactive gold nanoparticles were reported as effective radiosensitizers for CT imaging and radiotherapy of tumors. They enable on-site immobilization within tumors resulting in enhanced accumulation and retention.

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29

Goto, Kei, Keiichi Shimada, Shunsuke Furukawa, Shinji Miyasaka, Yusuke Takahashi, and Takayuki Kawashima. "Formation of a Stable Sulfenic Acid by Hydrolysis of a Thionitrate and a Sulfenyl Bromide." Chemistry Letters 35, no. 8 (2006): 862–63. http://dx.doi.org/10.1246/cl.2006.862.

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30

Souto, José A., Willian Lewis, and Robert A. Stockman. "Isolation of stable non cyclic 1,2-disulfoxides. Revisiting the thermolysis of S-aryl sulfinimines." Chem. Commun. 50, no. 84 (2014): 12630–32. http://dx.doi.org/10.1039/c4cc05751a.

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The thermolysis of S-aryl sulfinimines is shown to generate 1,2-disulfoxides and disulfides via initial Cope elimination, dimerisation of the produced sulfenic acid to a thiosulfinate, and subsequent disproportionation of the thiosulfinate.

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31

Pan, Jia, and Kate S. Carroll. "Light-Mediated Sulfenic Acid Generation from Photocaged Cysteine Sulfoxide." Organic Letters 17, no. 24 (2015): 6014–17. http://dx.doi.org/10.1021/acs.orglett.5b02981.

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32

Turell, Lucía, Horacio Botti, Sebastián Carballal, Rafael Radi, and Beatriz Alvarez. "Sulfenic acid—A key intermediate in albumin thiol oxidation." Journal of Chromatography B 877, no. 28 (2009): 3384–92. http://dx.doi.org/10.1016/j.jchromb.2009.03.035.

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33

Pople, Jasmine M. M., and Justin M. Chalker. "A critical evaluation of probes for cysteine sulfenic acid." Current Opinion in Chemical Biology 60 (February 2021): 55–65. http://dx.doi.org/10.1016/j.cbpa.2020.07.011.

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34

Freeman, Fillmore, Ifeoluwa Taiwo Adesina, Julie Le La, Joseph Yonghun Lee, and Amelia Ann Poplawski. "Conformers of Cysteine and Cysteine Sulfenic Acid and Mechanisms of the Reaction of Cysteine Sulfenic Acid with 5,5-Dimethyl-1,3-cyclohexanedione (Dimedone)." Journal of Physical Chemistry B 117, no. 50 (2013): 16000–16012. http://dx.doi.org/10.1021/jp409022m.

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35

Yuan, Hong, and Zhihua Sun. "Acid-Catalyzed Synthesis of Aryl[4,5]isothiazoles through a Sulfenic Acid Pathway." Synlett 30, no. 16 (2019): 1904–8. http://dx.doi.org/10.1055/s-0039-1690201.

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A new method to efficiently prepare 3-substituted aryl[4,5]isothiazoles by simply heating the starting materials with a catalytic amount of p-toluenesulfonic acid in toluene is reported. This simple procedure is well suitable for a variety of substrates that can tolerate substitution changes in the fusing aromatic ring, as well as at the 3-position. Substituted aryl rings of varying electronic properties and alkyl substitution eventually afford aryl[4,5]isothiazoles in high yields.

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36

Yoshimura, Toshiaki, Kazuhiro Hamada, Satoru Yamazaki, Choichiro Shimasaki, Shin Ono, and Eiichi Tsukurimichi. "Model Reaction of Self-Condensation of Sulfenic Acids. Kinetic Investigation for the Reaction of Methyl Benzenesulfenate withtrans-Decalin-9-sulfenic Acid and 2-Methyl-2-propanesulfenic Acid." Bulletin of the Chemical Society of Japan 68, no. 1 (1995): 211–18. http://dx.doi.org/10.1246/bcsj.68.211.

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37

Johansson, Magnus, and Mathias Lundberg. "Glutathionylation of beta-actin via a cysteinyl sulfenic acid intermediary." BMC Biochemistry 8, no. 1 (2007): 26. http://dx.doi.org/10.1186/1471-2091-8-26.

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38

Chatelle, Claire, Stéphanie Kraemer, Guoping Ren, et al. "Converting a Sulfenic Acid Reductase into a Disulfide Bond Isomerase." Antioxidants & Redox Signaling 23, no. 12 (2015): 945–57. http://dx.doi.org/10.1089/ars.2014.6235.

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39

Roos, Goedele, and Joris Messens. "Protein sulfenic acid formation: From cellular damage to redox regulation." Free Radical Biology and Medicine 51, no. 2 (2011): 314–26. http://dx.doi.org/10.1016/j.freeradbiomed.2011.04.031.

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40

Qian, Jiang, Chananat Klomsiri, Stephen B. King, Leslie B. Poole, Allen W. Tsang, and Cristina M. Furdui. "Simple Synthesis of Chemical Probes for Labeling Sulfenic Acid Proteins." Free Radical Biology and Medicine 51 (November 2011): S20. http://dx.doi.org/10.1016/j.freeradbiomed.2011.10.045.

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41

YOSHIMURA, T., E. TSUKURIMICHI, S. YAMAZAKI, S. SOGA, C. SHIMASAKI, and K. HASEGAWA. "ChemInform Abstract: Synthesis of a Stable Sulfur Acid, trans-Decalin-9-sulfenic Acid." ChemInform 23, no. 51 (1992): no. http://dx.doi.org/10.1002/chin.199251165.

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42

Saurin, A. T., H. Neubert, J. P. Brennan, and P. Eaton. "Widespread sulfenic acid formation in tissues in response to hydrogen peroxide." Proceedings of the National Academy of Sciences 101, no. 52 (2004): 17982–87. http://dx.doi.org/10.1073/pnas.0404762101.

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43

Alcock, Lisa J., Bruno L. Oliveira, Michael J. Deery, et al. "Norbornene Probes for the Detection of Cysteine Sulfenic Acid in Cells." ACS Chemical Biology 14, no. 4 (2019): 594–98. http://dx.doi.org/10.1021/acschembio.8b01104.

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44

Poole, Leslie B., Bu-Bing Zeng, Sarah A. Knaggs, Mamudu Yakubu, and S. Bruce King. "Synthesis of Chemical Probes to Map Sulfenic Acid Modifications on Proteins." Bioconjugate Chemistry 16, no. 6 (2005): 1624–28. http://dx.doi.org/10.1021/bc050257s.

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45

Heinecke, Julie, and Peter C. Ford. "Formation of Cysteine Sulfenic Acid by Oxygen Atom Transfer from Nitrite." Journal of the American Chemical Society 132, no. 27 (2010): 9240–43. http://dx.doi.org/10.1021/ja102221e.

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46

ZIELINSKI, M., and M. KANSKA. "ChemInform Abstract: Syntheses and Uses of Isotopically Labeled Sulfenic Acid Derivatives." ChemInform 22, no. 22 (2010): no. http://dx.doi.org/10.1002/chin.199122316.

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47

OKUYAMA, T. "ChemInform Abstract: Mechanistic Aspects of Nucleophilic Substitutions of Sulfenic Acid Derivatives." ChemInform 22, no. 25 (2010): no. http://dx.doi.org/10.1002/chin.199125290.

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48

Clennan, Edward L. "The Reactions of Sulfides and Sulfenic Acid Derivatives with Singlet Oxygen." Sulfur reports 19, no. 1 (1996): 171–214. http://dx.doi.org/10.1080/01961779608047906.

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49

Chauhan, Rajat, Mark S. Mashuta, and Craig A. Grapperhaus. "Reinvestigation of the first structurally characterized metal-coordinated sulfenic acid complex." Inorganic Chemistry Communications 37 (November 2013): 186–88. http://dx.doi.org/10.1016/j.inoche.2013.09.045.

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50

Zyk, N. V., E. K. Beloglazkina, O. A. Lapshina, and T. A. Belova. "S-ArylN,N-dialkylamidothiosulfates, a novel class of sulfenic acid derivatives." Russian Chemical Bulletin 49, no. 8 (2000): 1478–80. http://dx.doi.org/10.1007/bf02495103.

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