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.
Freeman,Whenham
, p. 187 (1976)
Preparation method of sulfuryl thioester
-
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.
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.
