taurine chloramine

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: taurine chloramine
• 英文别名: Chloramine taurine
• 化学式: C₂H₇NO₃S*ClH₂N
• 分子量: 176.624
• InChiKey: YUELBIWMRGWXJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.07
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  115
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  牛磺酸 在 次氯酸 作用下， 生成 taurine chloramine
  参考文献：
  名称：

  One-electron oxidation and reduction of glycosaminoglycan chloramides: A kinetic study

  摘要：

  Hypochlorous acid and its acid-base counterpart, hypochlorite ions, produced under inflammatory conditions, may produce chloramides of glycosaminoglycans, these being significant components of the extracellular matrix (ECM). This may occur through the binding of myeloperoxidase directly to the glycosaminoglycans. The N-Cl group in the chloramides is a potential selective target for both reducing and oxidizing radicals, leading possibly to more efficient and damaging fragmentation of these biopolymers relative to the parent glycosaminoglycans. In this study, the fast reaction techniques of pulse radiolysis and nanosecond laser flash photolysis have been used to generate both oxidizing and reducing radicals to react with the chloramides of hyaluronan (HAG) and heparin (HepCl). The strong reducing formate radicals and hydrated electrons were found to react rapidly with both HACl and HepCl with rate constants of 1-1.7 x 10(8) and 0.7-12 x 10(8) M-1 s(-1) for formate radicals and 2.2 x 10(9) and 7.2 x 10(8) M-1 s(-1) for hydrated electrons, respectively. The spectral characteristics of the products of these reactions were identical and were consistent with initial attack at the N-Cl groups, followed by elimination of chloride ions to produce nitrogen-centered radicals, which rearrange subsequently and rapidly to produce C-2 radicals on the glucosamine moiety, supporting an earlier EPR study by M.D. Rees et al. (J. Am. Chem. Soc. 125: 13719-13733; 2003). The oxidizing hydroxyl radicals also reacted rapidly with HACl and HepCl with rate constants of 2.2 x 10(8) and 1.6 x 10(8) M-1 s(-1), with no evidence from these data for any degree of selective attack on the N-Cl group relative to the N-H groups and other sites of attack. The carbonate anion radicals were much slower with HACl and HepCl than hydroxyl radicals (1.0 x 10(5) and 8.0 x 10(4) M-1 s(-1), respectively) but significantly faster than with the parent molecules (3.5 x 10(4) and 5.0 x 10(4) M-1 s(-1), respectively). These findings suggest that these potential in vivo radicals may react in a site-specific manner with the N-Cl group in the glycosaminoglycan chloramides of the ECM, possibly to produce more efficient fragmentation. This is the first study therefore to conclusively demonstrate that reducing radicals react rapidly with glycosaminoglycan chloramides in a site-specific attack at the N-Cl group, probably to produce a 100% efficient biopolymer fragmentation process. Although less reactive, carbonate radicals, which may be produced in vivo via reactions of peroxynitrite with serum levels of carbon dioxide, also appear to react in a highly site-specific manner at the N-Cl group. It is not yet known if such site-specific attacks by this important in vivo species lead to a more efficient fragmentation of the biopolymers than would be expected for attack by the stronger oxidizing species, the hydroxyl radical. It is clear, however, that the N-Cl group formed under inflammatory conditions in the extracellular matrix does present a more likely target for both reactive oxygen species and reducing species than the N-H groups in the parent glycosaminoglycans. (C) 2013 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.freeradbiomed.2013.05.012
• 作为试剂：
  描述：

  bacillithiol 在 taurine chloramine 、 N-乙基马来酰亚胺 作用下， 以 水 为溶剂， 反应 0.5h， 以96.8%的产率得到bacillithiol disulfide
  参考文献：
  名称：

  髓过氧化物酶衍生的氧化剂氧化杆菌硫醇。

  摘要：

  芽孢杆菌硫醇是革兰氏阳性菌中主要的低分子量硫醇，包括人类病原体金黄色葡萄球菌。bacillithiol被认为是抵抗免疫系统产生的氧化剂的重要防御机制，尤其是源自髓过氧化物酶的次氯酸（HOCl）。但是，尚不清楚BSH与HOCl反应的速度如何以及在反应中形成了什么产物。在本研究中，我们使用了基于MRM的灵敏的LC-MS方法来表征无细胞溶液和金黄色葡萄球菌中BSH与HOCl的反应。在无细胞系统中，BSH主要以低摩尔比的HOCl和较高氧化剂浓度的亚磺酸和磺酸形成二硫键二聚体（BSSB）。HOCl也促进了杆菌硫醇磺酰胺的形成。在金黄色葡萄球菌的氧化模式相似，除了一小部分的BSH还会与蛋白质硫醇形成混合的二硫化物。 利用与蛋氨酸的竞争，我们确定HOCl与BSH反应的二级速率常数为6×10 7  M -1 s -1，这表明反应是快速的，接近扩散控制的反应。其他反应性卤素物质，包括次硫氰酸（HOSCN），

  DOI：

  10.1016/j.freeradbiomed.2020.06.009

文献信息

• Assay for detecting inhibitors of the enzyme mueloperokidase
  申请人：——

  公开号：US20040142407A1

  公开（公告）日：2004-07-22

  An assay for detecting inhibitors of the enzyme myeloperoxidase said method comprising: reacting myeloperoxidase with hydrogen peroxide and a chloride source to generate hypochlorus acid in the presence of a potential inhibitor of said myeloperoxidase; reacting any formed hypochlorous acid with a suitable amine to form the corresponding chloramine; Optionally removing any unreacted hydrogen peroxide; reacting any formed chloramine with a suitable detector molecule in the presence of iodide to form oxidised detector molecule; determining the amount of formed oxidised detector molecule by measuring the absorbance or fluorescence at a suitable wavelength; Identifying as inhibitors of myeloperoxidase those compounds which cause the amount of formed oxidised detector molecule to be decreased. And for use in diagnostic tests for myeloperoxidase activity is disclosed.

  一种用于检测酶类嗜酸性粒细胞过氧化物酶抑制剂的测定方法，包括以下步骤：在可能存在酶抑制剂的情况下，将嗜酸性粒细胞过氧化物酶与过氧化氢和氯化物源反应以生成次氯酸；将生成的任何次氯酸与适当的胺反应以形成相应的氯胺；可选地去除任何未反应的过氧化氢；将生成的任何氯胺与适当的探测分子在碘化物存在下反应，以形成氧化的探测分子；通过在适当波长处测量吸收或荧光来确定生成的氧化探测分子的数量；将导致生成的氧化探测分子的数量减少的化合物确定为嗜酸性粒细胞过氧化物酶的抑制剂。并且还公开了用于嗜酸性粒细胞过氧化物酶活性诊断测试的用途。