1113-13-9Relevant articles and documents
Simple alkanethiol groups for temporary blocking of sulfhydryl groups of enzymes
Smith,Maggio,Kenyon
, p. 766 - 771 (1975)
New reagents for the temporary blocking of active or accessible sulfhydryl groups of enzymes have been developed. These reagents, which are either alkyl alkane thiolsulfonates or alkoxycarbonyl alkyl disulfides, rapidly and quantitatively place various RS- groups on the sulfhydryls to generate mixed disulfides. In all cases native enzymes can be regenerated with either dithiothreitol or β mercaptoethanol. In general the temporary blocking groups also afford total protection against normally inhibitory thiol blocking agents. When RS- groups were attached to rabbit muscle creatine kinase (EC 2.7.3.2), a trend toward lower residual activities with increasing bulk was observed. Treatment of the native creatine kinase with 14CH3HgCl led to incorporation of greater than 1 equiv of CH3Hg- group per subunit. This CH3Hg blocked enzyme was fully active, and the blocking group afforded no protection against iodoacetamide. These results suggest that CH3Hg- and the RS- groups are modifying two different sulfhydryl groups on the enzyme. When papain (EC 3.4.4.10) was treated with excess methyl methane thiol sulfonate, complete and rapid inhibition was observed, and 1 equiv of CH3S- was incorporated/mol of active enzyme. Complete protection against normally inhibitory 5,5' dithiobis (2 nitrobenzoic acid) was afforded by the temporary blocking group. When rabbit muscle glyceraldehyde 3 phosphate dehydrogenase (EC 1.2.1.12) was titrated with methyl methane thiol sulfonate, two sulfhydryl groups per subunit were found to be modified, one much more rapidly than the other. If one extrapolates the initial slope of the titration curve, the inactivation of the enzyme would be complete after modification of a single cysteinyl residue per subunit.
Rapid and highly chemoselective biomimetic oxidation of organosulfur compounds with tetrabutylammonium peroxymonosulfate in the presence of manganese meso-tetraphenylporphyrin and imidazole
Iranpoor, Nasser,Mohajer, Daryoush,Rezaeifard, Abdol-Reza
, p. 3811 - 3815 (2004)
A novel and efficient method is described for the immediate oxidation of different organosulfur compounds using tetrabutylammonium peroxymonosulfate in the presence of manganese meso-tetraphenylporphyrin and imidazole. The method is highly chemoselective and the yields are excellent.
Preparation method of sulfuryl thioester
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Paragraph 0030-0033; 0042-0044, (2021/11/10)
The invention provides a preparation method of sulfuryl thioester, which uses mercaptan as a starting material. The hydrogen peroxide is an oxidizing agent, an alkali metal halide or an alkaline earth metal halide is used as an additive to prepare the sulfuryl thioester. The product obtained by the method is high in purity and low in production cost, avoids introducing a metal oxidant, can be used for industrial production, and has a good application prospect.
External Oxidant-Free Oxidative Tandem Cyclization: NaI-Catalyzed Thiolation for the Synthesis of 3-Thiosubstituted Pyrroles
Yuan, Bingxiang,Jiang, Yong,Qi, Zhenjie,Guan, Xin,Wang, Ting,Yan, Rulong
supporting information, p. 5112 - 5117 (2019/11/11)
A simple method for the synthesis of 3-thiosubstituted pyrroles from homopropargylic amines and thiosulfonates via a tandem sulfenylation/cyclization has been developed. The thiosulfonates are used both as substrates and oxidants in this transformation. This procedure exhibits good functional group tolerance and a series of 3-thiosubstituted pyrrole derivatives was obtained in moderate to good yields. (Figure presented.).
Electrochemical oxidations of thioethers: Modulation of oxidation potential using a hydrogen bonding network
Liu, Shiwen,Chen, Bocheng,Yang, Yi,Yang, Yuhao,Chen, Qianjin,Zeng, Xiaojun,Xu, Bo
, (2019/11/28)
A highly efficient chemo-selective electrochemical oxidation of thioethers to sulfoxides and sulfones was developed. The hydrogen bonding network generated from hexafluoro-2-propanol (HFIP) and acetic acid (AcOH) plays an important role in the modulation of oxidation potential. The hydrogen bonding network complexes strongly with the sulfoxide, making it less prone to further oxidation. Therefore, thioethers can be selectively electrochemically oxidized to sulfoxides and over-oxidization could be minimized. Moreover, this modulation of oxidization via hydrogen bonding was supported by density functional theory (DFT) calculations and cyclic voltammetry experiments.
Dinitrogen Tetroxide Impregnated Activated Charcoal (N2O 4/Charcoal): Selective Oxidation of Sulfides to Sulfoxides and Bisulfides to Thiosulfonates
Iranpoor, Nasser,Firouzabadi, Habib,Pourali, Ali-Reza
, p. 347 - 349 (2007/10/03)
Dinitrogen tetroxide was easily impregnated on activated charcoal to give a stable heterogeneous reagent (N2O4/charcoal). The chemoselective oxidation of sulfides to sulfoxides in the presence of different sensitive functional groups was achieved using this reagent in CH 2Cl2 at room temperature. Dialkyl sulfides were also selectively converted to their corresponding sulfoxides in the presence of diaryl or alkyl-aryl sulfides. Oxidation of disulfides to thiosulfonates without any over oxidation was also performed at room temperature by this system.
Carbapenem derivatives
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, (2008/06/13)
Disclosed is a novel carbapenem derivative having a substituted imidazo[5,1-b]thiazole group at the 2-position on the carbapenem ring have high anti-microbial activities against β-lactamase producing bacteria, MRSA, resistant-Pseudomonas aeruginosa, PRSP, enterococci, and influenza, and high stabilities to DHP-1. According to the present invention, there is provided a compound represented by the formula (I), or a pharmacologically acceptable salt thereof or an ester at the 3-position on the carbapenem ring thereof:
An easy and practical synthesis of symmetrical thiosulfonic S-esters
Chemla, Fabrice
, p. 894 - 896 (2007/10/03)
Symmetrical alkyl and aryl thiosulfonic S-esters were prepared in good to excellent yields by the acetyl chloride-activated zinc reduction of sulfonyl chlorides.
Palladium-catalysed Hydrosulfination: Synthesis of Sulfonic Acids and S-Alkyl Alkanethiosulfonates from Alkenes, Sulfur Dioxide and Hydrogen
Keim, Wilhelm,Herwig, Juergen
, p. 1592 (2007/10/02)
S-Alkyl alkanethiosulfonates and sulfonic acids can easily be synthesized from sulfur dioxide, alkenes, hydrogen and a cationic palladium(II)-diphosphine complex like 2 1 , at temperatures above the ceiling temperature of the SO2-alkene copolymer.