Cysteine thiyl radical | 35772-84-0

• 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
• 英文名称: Cysteine thiyl radical
• 英文别名: L-cystein-S-yl
• CAS: 35772-84-0
• 化学式: C₃H₆NO₂S
• 分子量: 120.152
• InChiKey: BQXFQDOHKMTBDK-REOHCLBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  7
• 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：
  64.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Cysteine thiyl radical 在 氧气 作用下， 以 various solvent(s) 为溶剂， 生成 Cysteine thiylperoxy radical
  参考文献：
  名称：

  New Reactions of Electronically Excited Radicals Grafted to SiO₂ Surface and in Solids

  摘要：

  Some new reactions of electronically excited radicals (vinyl, cyclohexadienyl, peroxy and thiylperoxy) were investigated both by the traditional method (in solid freezing matrices of different nature) and through the use of matrix isolation method on chemically activated silica surface (RSi).

  DOI：

  10.1080/10587259408027168
• 作为产物：
  描述：

  L-胱氨酸 在 大鼠1,25-二羟基维生素D(1,25(OH)2D)试剂盒 、 一氧化二氮 作用下， 以 水 为溶剂， 生成 Cysteine thiyl radical
  参考文献：
  名称：

  电子自旋共振研究电子辐照水溶液中产生的有机硫自由基。用硝基甲烷氨基阴离子和2-甲基-2-亚硝基丙烷自旋捕集

  摘要：

  DOI：

  10.1021/j150669a038

文献信息

• Electron spin resonance spin trapping of thiyl, radicals from the decomposition of thionitrites
  作者：P.David Josephy、Detlef Rehorek、Edward G. Janzen

  DOI：10.1016/s0040-4039(01)81144-8

  日期：1984.1

  Alkyl thiyl radicals produced by the homolytic decomposition of thionitrites are detected by ESR spin trapping using 5,5-dimethyl-1-Δ-pyrroline-N-oxide (DMPO).

  使用5，5-二甲基-1-Δ-吡咯啉-N-氧化物（DMPO）通过ESR自旋捕集检测由亚硫氰酸盐的均相分解产生的烷基噻吩基。
• 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
• Direct rate constant measurement of radical disulphide anion formation for cysteine and cysteamine in aqueous solution
  作者：Stephen P. Mezyk

  DOI：10.1016/0009-2614(95)00100-i

  日期：1995.3

  pulse radiolysis, laser photolysis and absorption spectroscopy have been used to directly determine rate constants for radical disulphide anion formation for cysteine and cysteamine in aqueous solution. The measured values for cysteine, over the pH range 7–12, allowed calculation of individual rate constants for the constituent reactions RS. + RSH → RSSR−. + H+ and RS. + RS− → RSSR−. as (3.39 ± 0.31)

  脉冲辐射分解，激光光解和吸收光谱技术已被直接用于确定水溶液中半胱氨酸和半胱胺的自由基二硫化物阴离子形成的速率常数。在7-12的pH范围内，半胱氨酸的测量值可以计算出组成反应RS的各个速率常数。+ RSH→RSSR −。+ H +和RS 。+ RS - →RSSR - 。如（3.39±0.31）×10 8和（1.21±0.04）×10 9 dm 3 mol -1 s -1， 分别。对于半胱胺类似值也通过该技术确定为（3.06±0.16）×10 8和（3.65±0.07）×10 9分米3摩尔-1小号-1。
• Kinetics of One-Electron Oxidation of Thiols and Hydrogen Abstraction by Thiyl Radicals from .alpha.-Amino C-H Bonds
  作者：Rong Zhao、Johan Lind、Gabor Merenyi、Trygve E. Eriksen

  DOI：10.1021/ja00105a048

  日期：1994.12

  One-electron oxidation of cysteine, homocysteine, and glutathione by azide radical in alkaline solution (pH 10.5), where both the amino and the SH groups are deprotonated, has been investigated by pulse radiolysis. Reducing alpha-aminoalkyl radicals ((.)CR), which are formed via intramolecular rearrangement of thiyl radicals, were detected using methylviologen as oxidant in the kinetic analysis. The general scheme of the reactions is sketched. Thiyl radicals either equilibrate with RSSR(.-) in reaction 5, RS(.) + RS(-) = RSSR(.-), or undergo intramolecular transformation via equilibrium 6, RS(.) = (.)CR. At pH 10.5, equilibrium 6 is completely shifted to the right, resulting in alpha-aminoalkyl radical formation. The rate constants in the reaction scheme for cysteine, homocysteine, and glutathione were measured. With the rate constants obtained, the decay kinetics of RSSR(.-) into (.)CR was simulated, and it agreed with that measured at 420 nm. At pH 10.5, the first-order rate constants for the transformation (k(6)) were determined to be 2.5 x 10(4), 1.8 x 10(5) and 2.2 x 10(5) s(-1) for cysteine, homocysteine, and glutathione, respectively. The rate constants for intermolecular hydrogen abstraction by thiyl radicals from alpha-amino C-H bonds of alanine and glycine were determined at the same pH to be 7.7 x 10(5) and 3.2 x 10(5) M(-1) s(-1), respectively. Thermodynamic estimation places the reduction potential E degrees(H2NC(CO2-)CH3)(.), H+/H2NCH(CO2-)CH3) at ca. 1.22 V, which implies a rather weak tertiary C-H bond in the anion of alpha-amino acids. Thus, an intramolecular hydrogen abstraction mechanism for the transformation of thiyl radical to alpha-amino carbon-centered radical is postulated. Molecular geometry plays an important part in deciding the transformation rates (k(6)) of different thiyl radicals.
• Lal, Manohar; Mahal, H. S., Canadian Journal of Chemistry, 1990, vol. 68, # 8, p. 1376 - 1382
  作者：Lal, Manohar、Mahal, H. S.

  DOI：——

  日期：——