| 41858-96-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• CAS: 41858-96-2
• 化学式: C₃H₆NO₂S₂
• 分子量: 152.218
• InChiKey: FMTOKBQQJZPAGV-REOHCLBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  89.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  L-胱氨酸 以 水 为溶剂， 生成 Cysteine thiyl radical 、
  参考文献：
  名称：

  Perthiyl radicals, trisulfide radical ions, and sulfate formation: a combined photolysis and radiolysis study on redox processes with organic di- and trisulfides

  摘要：

  The formation of perthiyl and thiyl radicals has been studied in a combined photochemical and radiation chemical investigation of the di- and trisulfides of penicillamine and cysteine, together with glutathione disulfide, cystamine dihydrochloride, and dithiodiglycolic acid in aqueous solution. The highest RSS. yields are found from the trisulfides with little difference between PenSSSPen and CySSSCy in the case of photolysis, but with a (4-5):1 ratio in favor in PenSS. over CySS. upon radiation chemically induced processes. Thiyl radicals are the other major species formed. The RSS./RS. ratio changes significantly depending on the nature of the di- or trisulfide and the method of radical generation employed. Perthiyl radicals are found to be moderately good oxidants, weaker though than thiyl radicals, and readily react with molecular oxygen in an addition process. The following absolute rate constants have been measured: k(PenSS. + ascorbate) = (4.1 +/- 1.0) x 10(6) M-1 s-1 and k(PenSS. + O2) = (5.1 +/- 1.0) x 10(6) M-1 s-1. Probably the most interesting finding about perthiyl radicals is that inorganic SO42- is formed in their reaction with molecular oxygen. The mechanism of sulfate formation is suggested to proceed via the perthioperoxyl radical, RSSOO., structural rearrangement of this transient into the corresponding sulfonyl-type radical, RSSO2., addition of oxygen to the latter to yield a sulfonyl peroxyl, RSSO2OO., followed by a bimolecular radical-radical reaction of these peroxyl radicals (in analogy to the fate of peroxyl radicals in general) leading to RSSO3.. Cleavage of SO3 from RSSO3. and hydrolysis would then result in SO42-. Reduction of trisulfides yields (RSSSR).- radical anions which decay into either RSS. + RS- (preferred pathway in case of PenSSSPen reduction; k{PenSSSPen + e(aq)-} = 2.0 x 10(10) M-1 s-1, k{PenSSSPen + CO2.-} = 2.3 x 10(8) M-1 s-1), or RS. + RSS- (preferred pathway in case of CySSSCy reduction). Trisulfide radical anions could directly be identified in the case of the cysteine compound with (CySSSCy).- absorbing at 425 nm and exhibiting a half-life of ca 4-mu-s. Radical cations (PenSSSPen).+ are indicated in the oxidation of penicillamine trisulfide.

  DOI：

  10.1021/j100180a058

文献信息

• Protein thiyl radicals in disordered systems: A comparative EPR study at low temperature
  作者：Günter Lassmann、Matthias Kolberg、Günther Bleifuss、Astrid Gräslund、Britt-Marie Sjöberg、Wolfgang Lubitz

  DOI：10.1039/b302601a

  日期：——

  environment (hydrogen bonding to the sulfur) of the thiyl radicals, as well as unusual anisotropic relaxation of the radicals have been observed. The stability of the thiyl radicals in various matrices was studied, including their reactions with oxygen and thiols in the matrix, which give rise to secondary radicals. The EPR line shape of alkyl thiyl radicals in disordered systems is characterized by an axial

  报告了在蛋白质和低分子量硫醇的各种条件下，关于无序系统中烷基硫基自由基的 EPR 光谱特性的系统研究。在 77 K 下通过紫外光解产生硫自由基，并在此温度下在大肠杆菌核糖核苷酸还原酶 (RNR) 和牛血清白蛋白 (BSA) 的 R1 蛋白、冻干 BSA 和 BSA 薄膜中的冷冻水溶液中进行研究，并且为了比较，在半胱氨酸的冷冻水溶液和多晶半胱氨酸中。已经观察到 g-张量与硫基自由基的环境极性（氢键合到硫）的相关性，以及自由基的不寻常的各向异性弛豫。研究了硫基自由基在各种基质中的稳定性，包括它们与基质中的氧和硫醇的反应，这会产生二次自由基。无序体系中烷基硫基自由基的EPR线形具有轴对称的大g各向异性，g⊥分量强，g∥分量宽而弱。相当大的 g 应变，在蛋白质中，许多不同的硫自由基位点极大地拓宽了冷冻玻璃光谱中的 g|| 分量。然而，g∥ 在 X 波段光谱中也完全解析，在无序系统中也是如此。BSA