73243-12-6Relevant academic research and scientific papers
Nonenzymatic, self-elimination degradation mechanism of glutathione
Deshmukh, Manjeet,Kutscher, Hilliard,Stein, Stanley,Sinko, Patrick
body text, p. 527 - 539 (2010/04/23)
In the present in vitro studies, evidence is provided showing that glutathione (GSH) can undergo spontaneous, nonenzymatic auto-degradation. The initial cleavage of the Glu-Cys bond involves nucleophilic attack of the N-terminal amino group of GSH at the
Reactive sulfur species: Kinetics and mechanisms of the reaction of cysteine thiosulfinate ester with cysteine to give cysteine sulfenic acid
Nagy, Peter,Lemma, Kelemu,Ashby, Michael T.
, p. 8838 - 8846 (2008/03/12)
(Chemical Equation Presented) The kinetics and mechanisms of the reaction of cysteine with cysteine thiosulfinate ester in aqueous solution have been studied by stopped-flow spectrophotometry between pH 6 and 14. Two reaction pathways were observed for pH > 12: (1) an essentially pH-independent nucleophilic attack of cysteinate on cysteine thiosulfinate ester, and (2) a pH-dependent fast equilibrium protonation of cysteine sulfenate that is followed by rate-limiting comproportionation of cysteine sulfenic acid with cysteinate to give cystine. For 6 pH 12, the rate-determining reaction between cysteinate and cysteine thiosulfinate ester becomes pH-dependent due to the protonation of their amine groups. Hydrolysis of cysteine thiosulfinate ester does not play a role in the aforementioned mechanisms because the rate-determining nucleophilic attack by hydroxide is relatively slow.
Reactive sulfur species: Kinetics and mechanisms of the oxidation of cysteine by hypohalous acid to give cysteine sulfenic acid
Nagy, Peter,Ashby, Michael T.
, p. 14082 - 14091 (2008/04/04)
Cysteine sulfenic acid has been generated in alkaline aqueous solution by oxidation of cysteine with hypohalous acid (HOX, X = Cl or Br). The kinetics and mechanisms of the oxidation reaction and the subsequent reactions of cysteine sulfenic acid have been studied by stopped-flow spectrophotometry between pH 10 and 14. Two reaction pathways were observed: (1) below pH 12, the condensation of two sulfenic acids to give cysteine thiosulfinate ester followed by the nucleophilic attack of cysteinate on cysteine thiosulfinate ester and (2) above pH 10, a pH-dependent fast equilibrium protonation of cysteine sulfenate that is followed by rate-limiting comproportionation of cysteine sulfenic acid with cysteinate to give cystine. The observation of the first reaction suggests that the condensation of cysteine sulfenic acid to give cysteine thiosulfinate ester can be competitive with the reaction of cysteine sulfenic acid with cysteine.
Sulfenamides as prodrugs of NH-acidic compounds: A new prodrug option for the amide bond
Guarino, Victor R.,Karunaratne, Veranja,Stella, Valentino J.
, p. 4910 - 4913 (2008/02/12)
The objective of this report is to introduce the novel concept of utilizing sulfenamides as prodrugs for compounds containing an NH-acidic functionality, particularly weakly acidic amide-type functionalities (amides, ureas, carbamates, etc.). Included are the syntheses and physicochemical characterizations of some model sulfenamides to illustrate the promise of this new prodrug technology.
Chemical properties of N-chlorotaurine sodium, a key compound in the human defence system
Gottardi, Waldemar,Nagl, Markus
, p. 411 - 421 (2007/10/03)
N-Chlorotaurine (NCT) is known to play an important role in the human defence system. The already proved utility of the sodium salt as a disinfectant in human medicine suggested a thorough investigation of its chemical properties. Chlorine transfer to N-H groups (transhalogenation) and oxidation of thio and aromatic compounds represent its main reactions. Auto-chlorination causes disproportionation forming N,N-dichlorotaurine (NDCT) with Kd = [NDCT][taurine]/fa[NCT]2 aH+ = (4.5 ± 0.8) times; 106, while the reaction with ammonium releasing NH2Cl is characterised by KNHC2 = [NH2Cl][taurine]/[NCT][NH4+] fa2 = 0.02 ± 0.004. The verified unique stability and low-level reactivity of NCT are considered essential for its function in the mammalian defence system and its practical applicability, which manifests itself in an optimal compromise between microbicidal activity and toxicity.
