- Terpene ligands as the basis of catalytic systems for the asymmetric oxidation of phenylphenacyl sulfide
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Terpene ligands (1S,2S,5S)-3-[{2-[(2-hydroxybenzylidene)amino]ethyl}imino]- 2,6,6-trimethylbicyclo[3.1.1.]heptane-2-ol and 3-({2-[(2-hydroxy-2,6,6- trimethylbicyclo[3.1.1.]hept-3-ilidene)amino]ethyl}imino)-2,6, 6-trimethylbicyclo[3.1.1.]heptane-2-ol have
- Kuchin,Ashikhmina,Rubtsova,Dvornikova
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Read Online
- Chemical Property of 1-Dialkylamino-2-phenylthioethylene
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The olefins which are vicinally substituted by amino and phenylthio groups showed the reactivity as an enamine in the reactions with heterocumulenes and in cycloadditions with a 1,3-dipole and a 2-propenimine, giving a pyrazole derivative and a pyridine derivative, respectively.
- Agawa, Toshio,Ishikawa, Minori,Komatsu, Mitsuo,Ohshiro, Yoshiki
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Read Online
- RuCl2(PPh3)3: A new catalyst for diazocarbonyl insertions into heteroatom-hydrogen bonds
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The first ever use of RuCl2(PPh3)3 as a catalyst for diazoketone insertions into heteroatom-hydrogen bonds is described.
- Sengupta, Saumitra,Das, Debasis,Sen Sarma, Debarati
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Read Online
- Phenylthiomethyl Ketone-Based Fragments Show Selective and Irreversible Inhibition of Enteroviral 3C Proteases
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Lead structure discovery mainly focuses on the identification of noncovalently binding ligands. Covalent linkage, however, is an essential binding mechanism for a multitude of successfully marketed drugs, although discovered by serendipity in most cases. We present a concept for the design of fragments covalently binding to proteases. Covalent linkage enables fragment binding unrelated to affinity to shallow protein binding sites and at the same time allows differentiated targeted hit verification and binding location verification through mass spectrometry. We describe a systematic and rational computational approach for the identification of covalently binding fragments from compound collections inhibiting enteroviral 3C protease, a target with high therapeutic potential. By implementing reactive groups potentially forming covalent bonds as a chemical feature in our 3D pharmacophore methodology, covalent binders were discovered by high-throughput virtual screening. We present careful experimental validation of the virtual hits using enzymatic assays and mass spectrometry unraveling a novel, previously unknown irreversible inhibition of the 3C protease by phenylthiomethyl ketone-based fragments. Subsequent synthetic optimization through fragment growing and reactivity analysis against catalytic and noncatalytic cysteines revealed specific irreversible 3C protease inhibition.
- Schulz, Robert,Atef, Amira,Becker, Daniel,Gottschalk, Franziska,Tauber, Carolin,Wagner, Stefan,Arkona, Christoph,Abdel-Hafez, Atef A.,Farag, Hassan H.,Rademann, J?rg,Wolber, Gerhard
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Read Online
- Competition Between Cα-S and Cα-Cβ Bond Cleavage in β-Hydroxysulfoxides Cation Radicals Generated by Photoinduced Electron Transfer?
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A kinetic and product study of the 3-cyano-N-methyl-quinolinium photoinduced monoelectronic oxidation of a series of β-hydroxysulfoxides has been carried out to investigate the competition between Cα-S and Cα-Cβ bond cleavage within the corresponding cation radicals. Laser flash photolysis experiments unequivocally established the formation of sulfoxide cation radicals showing their absorption band (λmax ≈ 520?nm) and that of 3-CN-NMQ? (λmax ≈ 390?nm). Steady-state photolysis experiments suggest that, in contrast to what previously observed for alkyl phenyl sulfoxide cation radicals that exclusively undergo Cα-S bond cleavage, the presence of a β-hydroxy group makes, in some cases, the Cα-Cβ scission competitive. The factors governing this competition seem to depend on the relative stability of the fragments formed from the two bond scissions. Substitution of the β-OH group with -OMe did not dramatically change the reactivity pattern of the cation radicals thus suggesting that the observed favorable effect of the hydroxy group on the Cα-Cβ bond cleavage mainly resides on its capability to stabilize the carbocation formed upon this scission.
- Lapi, Andrea,D'Alfonso, Claudio,Del Giacco, Tiziana,Lanzalunga, Osvaldo
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p. 1310 - 1321
(2021/06/07)
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- A cascade deprotonation/intramolecular aldol reaction of α-carbonyl sulfonium ylides with 2-mercaptoindole-3-carbaldehydes and 2-mercaptobenzaldehydes to access thieno[2,3-b]indoles and benzothiophenes
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The first catalyst-free cascade deprotonation/intramolecular aldol reaction of α-carbonyl sulfonium ylides with 2-mercaptoindole-3-carbaldehydes and 2-mercaptobenzaldehydes was developed. A series of thieno[2,3-b]indoles and benzothiophenes were smoothly obtained in high to excellent yields. The salient features of the protocol include catalyst-free conditions, an environment-friendly solvent, broad substrate scope, and large-scale synthesis.
- Yang, Lei,Zhou, Shun,Zhao, Jian-Qiang,You, Yong,Wang, Zhen-Hua,Zhou, Ming-Qiang,Yuan, Wei-Cheng
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supporting information
p. 3678 - 3686
(2021/05/05)
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- Steric-Free Bioorthogonal Labeling of Acetylation Substrates Based on a Fluorine-Thiol Displacement Reaction
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We have developed a novel bioorthogonal reaction that can selectively displace fluorine substitutions alpha to amide bonds. This fluorine-thiol displacement reaction (FTDR) allows for fluorinated cofactors or precursors to be utilized as chemical reporters, hijacking acetyltransferase-mediated acetylation both in vitro and in live cells, which cannot be achieved with azide- or alkyne-based chemical reporters. The fluoroacetamide labels can be further converted to biotin or fluorophore tags using FTDR, enabling the general detection and imaging of acetyl substrates. This strategy may lead to a steric-free labeling platform for substrate proteins, expanding our chemical toolbox for functional annotation of post-translational modifications in a systematic manner.
- Lyu, Zhigang,Zhao, Yue,Buuh, Zakey Yusuf,Gorman, Nicole,Goldman, Aaron R.,Islam, Md Shafiqul,Tang, Hsin-Yao,Wang, Rongsheng E.
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supporting information
p. 1341 - 1347
(2021/02/01)
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- LINKING AMINO ACID SEQUENCES, MANUFACTURING METHOD THEREOF, AND USE THEREOF
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This invention provides compositions comprising linked amino acid sequences, pharmaceutical compositions comprising linked amino acid sequences, and methods of making thereof. This invention also provides methods of delivering said compositions to subjects and methods of treating various disorders and diseases using the said compositions.
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Page/Page column 13; 109; 112; 126-127
(2021/08/20)
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- Synthesis of benzofurans from the cyclodehydration of α-phenoxy ketones mediated by Eaton’s reagent
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Cyclodehydration of α-phenoxy ketones promoted by Eaton’s reagent (phosphorus pentoxide–methanesulfonic acid) is used to prepare 3-substituted or 2,3-disubstituted benzofurans with moderate to excellent yields under mild conditions. The method provides a facile access to benzofurans from readily available starting materials such as phenols and α-bromo ketones. The reaction is highly efficient, which is attributed to the good reactivity and fluidity of Eaton’s reagent. The reaction can be applied to prepare naphthofurans, furanocoumarins, benzothiophenes, and benzopyrans.
- Ma, Lin,Ma, Zhanwei,Zhang, Min,Zhou, Min
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p. 426 - 436
(2020/03/23)
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- Air-Induced Disulfenylation of Alkenes: Facile Synthesis of Vicinal Dithioethers
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A novel disulfenylation of alkenes with thiophenols and their corresponding disulfides by using air as the oxidant has been achieved. This transformation provides a facile and practical protocol for the synthesis of vicinal dithioethers under mild conditions.
- Chen, Danyao,Chen, Qian,Huang, Yuanting,Ou, Yingcong,Yan, Y.,Yu, Guodian
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supporting information
p. 83 - 86
(2019/12/30)
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- Air-stable binuclear Titanium(IV) salophen perfluorobutanesulfonate with zinc power catalytic system and its application to C–S and C–Se bond formation
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An air-stable μ-oxo-bridged binuclear Lewis acid of titanium(IV) salophen perfluorobutanesulfonate [{Ti(salophen)H2O}2O][OSO2C4F9]2 (1) was successfully synthesized by the reaction of TiIV(salophen)Cl2 with AgOSO2C4F9 and characterized by techniques such as IR, NMR and HRMS. This complex was stable open to air over a year, and exhibited good thermal stability and high solubility in polar organic solvents. The complex also had relatively strong acidity with a strength of 0.8 Ho ≤ 3.3, and showed high catalytic efficiency towards various C–S and C–Se bond formations in the presence of zinc power. This catalytic system affords a mild and efficient approach to synthesis of thio- and selenoesters, α-arylthio- and seleno-carbonyl compounds, and thio- and selenoethers.
- Wang, Lingxiao,Qiao, Jie,Wei, Jiancong,Liang, Zhiwu,Xu, Xinhua,Li, Ningbo
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- Iridium-Catalyzed Carbenoid Insertion of Sulfoxonium Ylides for Synthesis of Quinoxalines and β-Keto Thioethers in Water
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Sulfoxonium ylides as safe carbene precursors are described for iridium-catalyzed carbene insertions and annulation, providing a facile and green approach to access a variety of quinoxaline derivatives in water. This water-mediated method also allows the preparation of β-keto thioethers under mild condition.
- Xu, Yingying,Huang, Xin,Lv, Guanghui,Lai, Ruizhi,Lv, Songyang,Li, Jianglian,Hai, Li,Wu, Yong
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p. 4635 - 4638
(2020/07/04)
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- Rhodium-Catalyzed Rearrangement of S/Se-Ylides for the Synthesis of Substituted Vinylogous Carbonates
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An efficient rhodium-catalyzed unprecedented oxa-[2,3]-sigmatropic rearrangement of sulfur ylide derived from α-thioesters/ketones and diazo carbonyl compounds has been accomplished for the synthesis of various sulfur-tethered vinylogous carbonates in good to excellent yields. Important features of the developed reaction include wide functional group tolerance, excellent chemo- and regioselectivity, and efficient rearrangement involving the carbonyl motif. The present reaction also equally works well with α-selenoesters for the synthesis of seleno-containing vinylogous carbonates.
- Reddy, Angula Chandra Shekar,Anbarasan, Pazhamalai
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supporting information
p. 9965 - 9969
(2019/12/24)
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- Overcoming solid handling issues in continuous flow substitution reactions through ionic liquid formation
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Substitutions such as acylations, arylations, and alkylations are some of the most commonly run reactions for building complex molecules. However, the requirement of a stoichiometric base to scavange acid by-products creates significant challenges when operating in continuous flow due to solid handling issues associated with precipitating base·HX salts. We present a general and simple strategy to overcome these solid handling issues through the use of acid scavenging organic bases that generate low- to moderate-melting ionic liquids upon protonation. The application of these bases towards the most commonly run substitutions are demonstrated, enabling reactions to be run in flow without requiring additional equipment, specific solvents, or dilute reaction conditions to prevent clogging.
- Kashani, Saeed,Sullivan, Ryan J.,Andersen, Mads,Newman, Stephen G.
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supporting information
p. 1748 - 1753
(2018/04/30)
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- METHODS FOR LIGNIN DEPOLYMERIZATION USING THIOLS
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The disclosure relates to a method for depolymerizing lignin. The method includes reacting a lignin compound with a thiol compound to depolymerize the lignin compound and to form a depolymerized lignin product having a reduced molecular weight relative to the lignin compound prior to reacting. The method can further include forming an oxidized thiol reaction product between two thiol groups from one or more thiol compounds, and then reducing the oxidized thiol reaction product to re-form or regenerate the thiol compound for further lignin depolymerization.
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Paragraph 0084
(2018/11/22)
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- Preparation of Thioanisole Biscarbanion and C-H Lithiation/Annulation Reactions for the Access of Five-Membered Heterocycles
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The synthesis, isolation, and X-ray structure of a thioanisole-based trilithium complex are reported. On the basis of the double-lithiation strategy, two novel synthetic methodologies have been developed under mild reaction conditions (room temperature): (1) reactions of lithiated thioanisoles with nitriles give benzoisothiazoles via a [3 + 2]-type of approach with two new bond formations and (2) formation of benzothiophenes from thioanisoles and amides through a [4 + 1] pattern forming 4 new chemical bonds.
- Zhu, Ranran,Liu, Zheyuan,Chen, Jie,Xiong, Xiaoyu,Wang, Yuntao,Huang, Lin,Bai, Jinshan,Dang, Yanfeng,Huang, Jianhui
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p. 3161 - 3165
(2018/06/11)
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- One-pot synthesis of α-phenylsulfinyl ketones by reaction of phenyl benzenethiosulfinate with enolate anions, and synthesis of sulfoxides and sulfides by its reaction with Grignard reagents
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Phenyl benzenethiosulfinate reacts with enolate anions derived from ketones to give α-phenylsulfinyl ketones directly, together with minor amounts of α-phenylsulfanyl ketones. These are easily separated by forming the water-soluble sodium salts of the sulfinyl compounds. Grignard reagents also react with phenyl benzenethiosulfinate, to give mixtures of sulfoxides and sulfides.
- Fakhry, Jerome,Grayson, David H.
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p. 556 - 563
(2017/12/28)
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- Preparation method and application of novel ionic binuclear Schiff base titanium complex
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The invention provides a preparation method of a novel ionic binuclear Schiff base titanium complex and a synthetic method of applying the novel ionic binuclear Schiff base titanium complex to catalyze zinc powder and reduce disulfide or selenide to prepare sulfo(seleno) ester and dissymmetric sulfoether(selenide). The complex is a cationic binuclear Schiff base titanium complex, wherein titaniumatoms are bridged by oxygen atoms and are coordinated with a Schiff base ligand and a hydrone, and an ionic bond is formed by a cation part and an anion part of whole Schiff base titanium. The ionic binuclear Schiff base titanium complex is used as a catalyst, the zinc powder is used as a reducer, the disulfide(selenide) can be reduced and fractured, and the disulfide(selenide) can further and respectively react with anhydride, an alpha-bromo carbonyl compound and bromoalkane to prepare the sulfo(seleno) ester and the dissymmetric sulfoether(selenide). According to the preparation method provided by the invention, the defects that traditional lewis acid halide is deliquescent, an absolute solvent is used, conditions are strict and the like are overcome; an effective path for reducing the disulfide or selenide to prepare the sulfo(seleno) ester and the dissymmetric sulfoether(selenide) is provided, and the preparation method has the advantages of high yield, simpleness in operation andthe like.
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Paragraph 0081; 0082
(2018/04/03)
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- Copper Triflate Mediated α-Monohalogenation of α-Diazo β-Ketosulfones with Ammonium Halides
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Copper triflate mediated α-monohalogenation of α-diazo β-ketosulfones with ammonium halides provides the corresponding α-halo β-ketosulfones. Different metal triflates are investigated for this facile and efficient transformation. A plausible mechanism is proposed.
- Chan, Chieh-Kai,Wang, Heui-Sin,Hsu, Ru-Ting,Chang, Meng-Yang
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p. 2045 - 2056
(2017/04/26)
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- Stevens rearrangement of thioethers with arynes: A facile access to multi-substituted β-keto thioethers
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An effective method for the synthesis of multi-substituted β-keto thioethers via Stevens rearrangement of simple β-keto thioethers with arynes has been developed. In these reactions, successive C-S/C-H/C-C bonds were formed in one pot under mild and transition-metal free conditions to afford multi-substituted β-keto thioethers in moderate to good yields.
- Xu, Xiao-Bo,Lin, Zi-Hua,Liu, Yuyin,Guo, Jian,He, Yun
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supporting information
p. 2716 - 2720
(2017/04/03)
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- A route to benzylic arylsulfoxides from β-ketosulfoxides
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The K2CO3-mediated benzylation of β-ketosulfoxides 4 with 2.0?equiv of benzylic halides 5 affords benzylic arylsulfoxides 6 in moderate yields along with trace amounts of chalcones 7. The products 6 are assumed to form in situ intermediates of sulfenate anions from β-ketosulfoxides which are commonly involved in carbon–sulfur bond formation. A plausible mechanism has been proposed.
- Chang, Meng-Yang,Cheng, Yu-Chieh,Chan, Chieh-Kai
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p. 4068 - 4075
(2016/07/06)
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- Catalytic Asymmetric [4 + 1] Annulation of Sulfur Ylides with Copper-Allenylidene Intermediates
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The first copper-catalyzed asymmetric decarboxylative [4 + 1] cycloaddition of propargylic carbamates and sulfur ylides was successfully developed. This strategy led to a series of chiral indolines with synthetically flexible alkyne groups in good yields and with high enantio- and diastereoselectivities (up to 99% yield, 98% ee, and >95:5 dr). A possible mechanism and stereoinduction mode with copper-allenylidenes were proposed as the possible dipolar intermediate.
- Wang, Qiang,Li, Tian-Ren,Lu, Liang-Qiu,Li, Miao-Miao,Zhang, Kai,Xiao, Wen-Jing
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supporting information
p. 8360 - 8363
(2016/07/27)
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- Visible light mediated reductions of ethers, amines and sulfides
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Visible light-mediated photoredox catalysis enables the chemoselective reduction of activated carbon–heteroatom bonds as a function of reduction potential. The expansion of the scope of C–X bond reductions towards less activated motifs, such as ethers, amines and sulfides, is important to both organic synthesis and macromolecular degradation method development. In the present report, exploration of photoredox catalysis in alcoholic solvents mediated a decrease in the super-stoichiometric use of iPr2NEt and HCO2H in the reduction of α-keto ethers, amines and sulfides. Additionally, in the absence of fragmentation, [Formula presented] bond formation was afforded, suggesting an intermediate ketyl radicals are present in these transformations.
- Monos, Timothy M.,Magallanes, Gabriel,Sebren, Leanne J.,Stephenson, Corey R.J.
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p. 240 - 248
(2016/07/21)
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- Catalyst-Free Insertion of Sulfoxonium Ylides into Aryl Thiols. A Direct Preparation of β-Keto Thioethers
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Insertion of sulfoxonium ylides into the S-H bond of aryl thiols without the need for a catalyst is demonstrated, furnishing β-keto thioethers in excellent yield in most cases. The method overcomes traditional syntheses that employ metal catalysts in combination with diazo compounds or toxic and hard-prepared haloketones. The experimental setup consists of mixing the reagents in acetonitrile at room temperature. Additional experimental as well as kinetic isotopic effect studies give some insight into the mechanism of this reaction.
- Dias, Rafael M. P.,Burtoloso, Antonio C. B.
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p. 3034 - 3037
(2016/07/06)
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- Catalyst-Free Difunctionalization of Activated Alkenes in Water: Efficient Synthesis of β-Keto Sulfides and Sulfones
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Difunctionalization of activated alkenes, a powerful strategy in chemical synthesis, has been accomplished for direct synthesis of a series of β-keto sulfides and β-keto sulfones. The transformation, mediated by O2, proceeds smoothly in water and without any catalyst. Prominent advantages of this method include mild reaction conditions, purification simplicity, and gram-scale synthesis, underlining the practical utility of this methodology.
- Wang, Huamin,Wang, Guangyu,Lu, Qingquan,Chiang, Chien-Wei,Peng, Pan,Zhou, Jiufu,Lei, Aiwen
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p. 14489 - 14493
(2016/10/03)
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- Air oxidative radical hydroxysulfurization of styrenes leading to β-hydroxysulfides
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Air oxidative radical hydroxysulfurization of styrenes initiated by 0.5 mol % of tert-butyl hydroperoxide with arylthiols is described, and a new type of difunctionalization of alkenes was achieved.
- Zhou, Shao-Fang,Pan, Xiangqiang,Zhou, Zhi-Hao,Shoberu, Adedamola,Zou, Jian-Ping
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supporting information
p. 3682 - 3687
(2015/04/14)
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- Disulfide-based metal-free α-sulfanylation of ketones
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An eco-friendly methodology for the direct α-sulfanylation of ketones, has been developed. The procedure, based on the use of functionalized diaryldisulfides and catalyzed by d,l-proline, represents a mild and efficient approach for the preparation of α-arylthio-ketones.
- Vaquer, Andrea F.,Frongia, Angelo,Secci, Francesco,Tuveri, Enrica
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p. 96695 - 96704
(2015/11/24)
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- Fe-Mediated S-S Bond Cleavage and Its Application in the Synthesis of α-Arylthio Carbonyl Compounds
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In the presence of iron dust, diaryl disulfides react with α-bromo carbonyl compounds to obtain α-arylthio carbonyl compounds in good yield at 90 °C under an N2 atmosphere, using commercial dimethylformamide (DMF) as solvent. The possible reaction mechanism is that the disulfide is reduced by iron dust to give ArSFeSAr and then reacted with α-bromo carbonyl compounds to give product α-arylthio carbonyl compounds and FeBr2.
- He, Yun-Hua,Li, Ning-Bo,Chen, Jin-Yang,Qiu, Ren-Hua,Wang, Xie,Xu, Xin-Hua
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p. 1817 - 1822
(2015/08/06)
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- Palladium-catalyzed methylation of alkynyl C(sp)-H bonds with dimethyl sulfonium ylides
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A novel palladium-catalyzed methylation protocol for the synthesis of methyl-functionalized internal alkynes has been established. This methylation method is achieved through a C(sp)-C(sp3) bond formation process and represents a new synthetic application of sulfonium ylides.
- Liu, Yan-Yun,Yang, Xu-Heng,Huang, Xiao-Cheng,Wei, Wen-Ting,Song, Ren-Jie,Li, Jin-Heng
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p. 10421 - 10426
(2013/11/06)
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- Copper-Catalyzed Synthesis of α-Thioaryl Carbonyl Compounds Through S-S and C-C Bond Cleavage
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A method to access α-thioaryl ketones and α-thioaryl esters employing copper acetate (hydrate) as catalyst and readily accessible diaryl disulfides and β-diketones (or β-keto esters) has been developed. Both alkyl- and aryl-substituted carbonyl compounds can be prepared. Copyright
- Zou, Liang-Hua,Priebbenow, Daniel L.,Wang, Long,Mottweiler, Jakob,Bolm, Carsten
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supporting information
p. 2558 - 2563
(2013/10/21)
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- Gold-catalyzed carbene transfer to alkynes: Access to 2,4-disubstituted furans
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Furans of gold: The first example of a gold-catalyzed intermolecular addition of carbon ylides to terminal alkynes is reported (see scheme; DCE=dichloroethane, Tf=trifluoromethanesulfonyl). Subsequent intramolecular trapping of the generated gold carbene completes a formal [3+2] cycloaddition, which represents a novel synthesis of 2,4-disubstituted furans. Copyright
- Kramer, Soren,Skrydstrup, Troels
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supporting information; experimental part
p. 4681 - 4684
(2012/06/30)
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- Ago-allosteric modulators of human glucagon-like peptide 2 receptor
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Glucagon-like peptide 2 (GLP-2) is an intestinotropic peptide that binds to GLP-2 receptor (GLP-2R), a class-B G protein-coupled receptor (GPCR). Few synthetic agonists have been reported so far for class-B GPCRs. Here, we report the first scaffold compounds of ago-allosteric modulators for human GLP-2R, derived from methyl 2-{[(2Z)-2-(2,5-dichlorothiophen-3-yl)-2-(hydroxyimino) ethyl]sulfanyl}benzoate (compound 1).
- Yamazaki, Kazuto,Terauchi, Hiroki,Iida, Daisuke,Fukumoto, Hironori,Suzuki, Shuichi,Kagaya, Takaki,Aoki, Mika,Koyama, Koichiro,Seiki, Takashi,Takase, Kazuma,Watanabe, Misako,Arai, Tohru,Tsukahara, Kappei,Nagakawa, Junichi
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p. 6126 - 6135
(2012/10/30)
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- Synthesis of a wide range of thioethers by indium triiodide catalyzed direct coupling between alkyl acetates and thiosilanes
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An indium triiodide-catalyzed substitution of the acetoxy group in alkyl acetates with thiosilanes provides access to a variety of thioethers. The method is efficient for a wide scope of acetates such as primary alkyl, secondary alkyl, tertiary alkyl, allylic, benzylic, and propargylic acetates.
- Nishimoto, Yoshihiro,Okita, Aya,Yasuda, Makoto,Baba, Akio
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p. 1846 - 1849
(2012/06/18)
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- Modification and biological evaluation of novel 4-hydroxy-pyrone derivatives as non-peptidic HIV-1 protease inhibitors
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In this study, we have modified 4-hydroxy-pyran-2-ones, especially introduced heteroatoms (S or O) into the substituents, and detected their interactions with the binding pockets of HIV-1 protease (PR). The results indicated that the ethoxyl groups at C-2
- He, Meizi,Yang, Ning,Sun, Chunlai,Yao, Xiaojian,Yang, Ming
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experimental part
p. 200 - 209
(2012/03/10)
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- Photofunctional Eu3+/Tb3+ hybrids through sulfoxide linkages: Coordination bonds construction, characterization and luminescence
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New kinds of organic-inorganic hybrid materials consisting of rare earth (Eu3+, Tb3+) complexes covalently bonded to a silica-based network have been obtained by a sol-gel approach. Three novel versatile molecular building blocks con
- Guo, Lei,Yan, Bing,Liu, Jin-Liang
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experimental part
p. 4933 - 4940
(2011/06/27)
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- Cu-catalyzed one-pot synthesis of unsymmetrical diaryl thioethers by coupling of aryl halides using a thiol precursor
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An efficient Cu-catalyzed one-pot approach for the synthesis of unsymmetrical diaryl thioethers using potassium ethyl xanthogenate as a thiol surrogate is developed. This new protocol avoids usage of intricate thiols and makes use of its easily available xanthate as a precursor, and thiol will be generated in situ to prepare the diaryl thioethers through a Cu-catalyzed double arylation. This strategy was further successfully utilized for the synthesis of symmetrical diaryl thioethers, aryl alkyl thioethers, and benzothiazoles. (Figure Presented)
- Prasad,Sekar, Govindasamy
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supporting information; experimental part
p. 1008 - 1011
(2011/05/08)
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- Diphenyl diselenide-assisted α-phenylthiolation of carbonyl compounds with diphenyl disulfide
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For the cesium carbonate-catalyzed α-phenylthiolation of carbonyl compounds with diphenyl disulfide, the yields of the α-phenylthio carbonyl compounds were dramatically improved by the addition of a catalytic amount of diphenyl diselenide.
- Anbou, Hiroaki,Umeda, Rui,Nishiyama, Yutaka
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experimental part
p. 1248 - 1250
(2012/01/31)
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- 5-MEMBERED HETEROCYCLIC COMPOUND
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Provided is a compound having a superior acid secretion suppressive action, which shows an antiulcer activity and the like. A compound represented by the formula (I) or a salt thereof: wherein ring A is a saturated or unsaturated 5-membered heterocycle co
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Page/Page column 78-79
(2010/07/03)
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- Regioselective synthesis of 5-(arylsulfanyl)- and 5-(benzylsulfanyl)-6- phenylsalicylates by one-pot cyclizations of 1,3-bis(silyloxy)buta-1,3-dienes with 2-(arylsulfanyl)- and 5-(benzylsulfanyl)-3-ethoxy-1-phenylprop-2-en-1-ones
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5-(Arylsulfanyl)-6-phenylsalicylates were prepared by one-pot cyclizations of 1,3-bis(trimethylsilyloxy) buta-1,3-dienes with 2-(arylsulfanyl)-3-ethoxy-1- phenylprop-2-en-1-ones.
- Fatunsin, Olumide,Shkoor, Mohanad,Riahi, Abdolmajid,Hussain, Munawar,Villinger, Alexander,Fischer, Christine,Langer, Peter
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experimental part
p. 1610 - 1621
(2011/01/04)
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- An efficient fluorination of β-ketosulfones promoted by a room-temperature ionic liquid at ambient conditions under ultrasound irradiation using Selectfluor F-TEDA-BF4
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The fluorination reaction involving a β-ketosulfones by Selectfluor was efficiently promoted by the ionic liquid, [Hbim]BF4 (IL) as a reaction medium with methanol as co-solvent at room temperature under ultrasonic irradiation to afford the corresponding mono and difluoro-β-ketosulfones in excellent yields. The advantages of this method include among others the use of a recyclable, non-volatile ionic liquid, which promotes this protocol under room temperature without the requirement of any added catalyst under ultrasonic irradiation.
- Heravi, Mohammad Reza Poor
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body text
p. 1399 - 1402
(2011/10/08)
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- Rhodium-catalyzed organothio exchange reaction of α-organothioketones with disulfides
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RhH(PPh3)4 and 1,2-bis(diphenylphosphino)ethane (dppe) catalyzed the organothio exchange reaction of α-organothioketones and organic disulfides. The reaction was affected by the structure of the substrate: α-phenylthio and α-alkylthio aryl ketones reacted effectively with diaryl and dialkyl disulfides; α-phenylthio dialkyl ketones reacted with diaryl disulfides but not with dialkyl disulfides; diaryl disulfides with electron-donating p-substituents were more reactive than those with electron-withdrawing p-substituents.
- Arisawa, Mieko,Toriyama, Fumihiko,Yamaguchi, Masahiko
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experimental part
p. 1349 - 1352
(2010/12/24)
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- Cesium carbonate-Catalyzed α-phenylchalcogenation of carbonyl compounds with diphenyl dichalcogenide
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It was found that cesium carbonate has a unique catalytic ability on the reaction of carbonyl compounds with diphenyl diselenide to give the corresponding α-phenylseleno carbonyl compounds in moderate to good yields. Similarly, the α-phenylthiolation of c
- Nishiyama, Yutaka,Koguma, Yuya,Tanaka, Toshimasa,Umeda, Rui
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experimental part
p. 3367 - 3375
(2009/12/24)
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- Rhodium-catalyzed methylthio transfer reaction between ketone α-positions: Reversible single-bond metathesis of C-S and C-H bonds
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(Chemical Equation Presented) In the presence of a catalytic amount of RhH(PPh3)4 and 1,2-bis(diphenylposphino)ethane (dppe), α-phenylthio ketones were methylthiolated with ρ-cyano-α- methylthioacetophenone giving α-phenylthio-α-meth
- Arisawa, Mieko,Suwa, Katsunori,Yamaguchi, Masahiko
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supporting information; experimental part
p. 625 - 627
(2009/08/14)
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- On the reactivity of indium(III) benzenechalcogenolates (chalcogen = sulfur and selenium) towards organyl halides for the synthesis of organyl phenyl chalcogenides
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The reactivity of indium(III) benzenechalcogenolates (chalcogen = sulfur, selenium) towards organyl halides (organyl = alkyl, allyl, benzyl, acyl) was examined. A practical one-pot method to prepare organyl phenyl chalcogenides indium metal and diphenyl dichalcogenide was found. The coupling is fairly broad in scope and generally works better organyl halides capable to produce stable carbocations.
- Peppe, Clovis,Borges De Castro, Lierson
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experimental part
p. 678 - 683
(2009/10/30)
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- ACID SECRETION INHIBITOR
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The present invention provides a compound having a superior acid secretion inhibitory action, an antiulcer activity and the like. A proton pump inhibitor containing a compound represented by the formula (I) wherein ring A is a saturated or unsaturated 5- or 6-membered ring group optionally having, as a ring-constituting atom besides carbon atom, 1 to 4 hetero atoms selected from a nitrogen atom, an oxygen atom and a sulfur atom, ring-constituting atoms X1 and X2 are each a carbon atom or a nitrogen atom, a ring-constituting atom X3 is a carbon atom, a nitrogen atom, an oxygen atom or a sulfur atom, R1 is an optionally substituted aryl group or an optionally substituted heteroaryl group, R2 is an optionally substituted alkyl group, an optionally substituted aryl group or an optionally substituted heteroaryl group, R3 is an aminomethyl group optionally substituted by 1 or 2 lower alkyl groups, which is a substituent on a ring-constituting atom other than X1, X2 and X3, and ring A optionally further has substituent(s) selected from a lower alkyl group, a halogen atom, a cyano group and an oxo group, or a salt thereof or a prodrug thereof.
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Page/Page column 56
(2009/01/24)
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- α-Fluorination of β-ketosulfones by Selectfluor F-TEDA-BF4
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Attempted fluorination of β-ketosulfides using Selectfluor resulted only in the isolation of the corresponding diaryl disulfides, presumed to arise by decomposition of an unstable fluorinated intermediate. However, fluorination of β-ketosulfones using Selectfluor under anhydrous conditions does allow the isolation of both mono-and difluorinated products in moderate to good yields.
- Loghmani-Khouzani, Hossein,Poorheravi, Mohammad R.,Sadeghi, Majid M.M.,Caggiano, Lorenzo,Jackson, Richard F.W.
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p. 7419 - 7425
(2008/12/20)
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- Ionic liquid promoted regio- and stereo-selective thiolysis of epoxides-A simple and green approach to β-hydroxy- and β-keto sulfides
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A variety of epoxides underwent facile cleavage by thiols under the catalysis of 1-methyl-3-butylimidazolium bromide, [bmIm]Br, to produce the corresponding β-hydroxy sulfides with high regio- and stereo-selectivity. On the other hand, a specially designed basic ionic liquid, [bmIm]OH, efficiently catalyzes the thiolysis of ,β-epoxy ketones providing β-keto sulfides through simultaneous retro-aldol cleavages. The reactions are clean, high yielding, and do not require any organic solvent. The catalyst is also recycled. CSIRO 2007.
- Ranu, Brindaban C.,Mandal, Tanmay,Banerjee, Subhash,Dey, Suvendu S.
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p. 278 - 283
(2008/02/11)
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- Ionic liquid as catalyst and reaction medium: A simple, convenient and green procedure for the synthesis of thioethers, thioesters and dithianes using an inexpensive ionic liquid, [pmIm]Br
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An easily accessible and inexpensive room temperature ionic liquid, 1-pentyl-3-methylimidazolium bromide, [pmIm]Br efficiently catalyzes the reaction of alkyl halides or acyl halides with thiols without any solvent at room temperature leading to the synthesis of thioethers and thioesters in high yields. This reaction has also been extended for the preparation of dithianes and transthioetherification. The ionic liquid is recovered and recycled for subsequent runs.
- Ranu, Brindaban C.,Jana, Ranjan
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p. 1811 - 1818
(2007/10/03)
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- NaOH-Catalyzed Thiolysis of α,β-Epoxyketones in Water. A Key Step in the Synthesis of Target Molecules Starting from α,β -Unsaturated Ketones
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NaOH (0.02-0.3 molar equiv) is an efficient catalyst for the thiolysis reactions of α,β-epoxy ketones with alkyl and aryl thiols in water. Thiolysis of 3,4-epoxyheptan-2-one (1) with thiols 2a-d has been accomplished in mild conditions (30 °C and pH 6 or
- Fringuelli, Francesco,Pizzo, Ferdinando,Vaccaro, Luigi
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p. 2315 - 2321
(2007/10/03)
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- Indium(I) iodide-promoted cleavage of diaryl diselenides and disulfides and subsequent condensation with alkyl or acyl halides. One-pot efficient synthesis of diorganyl selenides, sulfides, selenoesters, and thioesters
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Diphenyl diselenides and disulfides undergo facile cleavages by indium(I) iodide and the corresponding generated selenate and thiolate anions condense in situ with alkyl or acyl halides present in the reaction mixture. Thus, a simple, efficient, and general procedure has been developed for the synthesis of unsymmetrical diorganyl selenides, sulfides (thioethers), selenoesters, and thioesters by this one-pot reaction at room temperature.
- Ranu, Brindaban C.,Mandal, Tanmay
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p. 5793 - 5795
(2007/10/03)
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- Metal substitution in thermolysin: Catalytic properties of tungstate thermolysin in sulfoxidation with H2O2
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The catalytic Zn2+ ion was extracted from thermolysin, which had been covalently bound to Eupergit C. The apo-enzyme incorporated the oxometallate anions MoO42-, SeO42-, and WO42- with partial restoration of the proteolytic activity. Tungstate thermolysin was moderately active in the sulfoxidation of thioanisole by hydrogen peroxide, whereas its activity towards phenylmercaptoacetophenone, which was designed to bind well in the active site of thermolysin, was much higher.
- Bakker, Martin,Van Rantwijk, Fred,Sheldon, Roger A.
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p. 622 - 625
(2007/10/03)
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- Spectral studies and configurational assignments of some 2-propenone derivatives
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3-(4-Substitutedphenyl)-1-phenyl-2-phenylthio-2-propen-1-ones (1-5) (1, R = H; 2, R = 4-OCH3; 3, R = 4-Cl; 4, R = 4-Br; 5, R = 4-NO2) have been synthesized by the condensation of 4-substituted benzaldehyde and phenacyl sulfide in pre
- Batterjee
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