89523-59-1Relevant academic research and scientific papers
A highly selective sulfinate ester probe for thiol bioimaging
Malwal, Satish R.,Labade, Ajay,Andhalkar, Abhijeet S.,Sengupta, Kundan,Chakrapani, Harinath
, p. 11533 - 11535 (2014)
We describe here hitherto unexplored chemistry of the sulfinate ester functional group as being highly selective towards nucleophilic substitution by thiols at physiological pH. Using this cleavable trigger, an optical thiol probe that is suitable for thi
Oxidation of disulfides to thiolsulfinates with hydrogen peroxide and a cyclic seleninate ester catalyst peroxide and a cyclic seleninate ester catalyst
McNeil, Nicole M. R.,McDonnell, Ciara,Hambrook, Miranda,Back, Thomas G.
, p. 10748 - 10762 (2015/08/11)
Cyclic seleninate esters function as mimetics of the antioxidant selenoenzyme glutathione peroxidase. They catalyze the reduction of harmful peroxides with thiols, which are converted to disulfides in the process. The possibility that the seleninate esters could also catalyze the further oxidation of disulfides to thiolsulfinates and other overoxidation products under these conditions was investigated. This has ramifications in potential medicinal applications of seleninate esters because of the possibility of catalyzing the unwanted oxidation of disulfide-containing spectator peptides and proteins. A variety of aryl and alkyl disulfides underwent facile oxidation with hydrogen peroxide in the presence of catalytic benzo-1,2-oxaselenolane Se-oxide affording the corresponding thiolsulfinates as the principal products. Unsymmetrical disulfides typically afforded mixtures of regioisomers. Lipoic acid and N,N′-dibenzoylcystine dimethyl ester were oxidized readily under similar conditions. Although isolated yields of the product thiolsulfinates were generally modest, these experiments demonstrate that the method nevertheless has preparative value because of its mild conditions. The results also confirm the possibility that cyclic seleninate esters could catalyze the further undesired oxidation of disulfides in vivo.
Model Reaction of Self-Condensation of Sulfenic Acids. Kinetic Investigation for the Reaction of Methyl Benzenesulfenate with trans-Decalin-9-sulfenic Acid and 2-Methyl-2-propanesulfenic Acid
Yoshimura, Toshiaki,Hamada, Kazuhiro,Yamazaki, Satoru,Shimasaki, Choichiro,Ono, Shin,Tsukurimishi, Eiichi
, p. 211 - 218 (2007/10/02)
Reaction of 2-methyl-2-propanesulfenic acid (1) with methyl arenesulfenates (2) gave S-aryl 2-methyl-2-propanethiosulfinates quantitatively, and kinetic investigation was carried out.Second-order rate dependence (first-order in methyl benzenesulfenate (2a
A GENERAL, HIGH-YIELD PREPARATION OF THIOSULFINATE ESTERS USING ORGANOTIN PRECURSORS
Harpp, David N.,Aida, T.,Chan, T. H.
, p. 5173 - 5176 (2007/10/02)
A variety of thiosulfinate esters are produced in >90percent isolated yield by the reaction of organotin thiolates with sulfinyl chlorides.
