S-nitroso-homocysteine

• 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: S-nitroso-homocysteine
• 英文别名: 2-Amino-4-nitrososulfanylbutanoic acid
• 化学式: C₄H₈N₂O₃S
• 分子量: 164.185
• InChiKey: QWPCKAAAWDCDCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.8
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  118
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  S-nitroso-homocysteine 在 乙二胺四乙酸 、 buffer reagents 、 维生素 C 作用下， 以 水 为溶剂， 生成 DL-高半胱氨酸 、 L-高胱氨酸
  参考文献：
  名称：

  Holmes, Anthony J.; Williams, D. Lyn H., Journal of the Chemical Society. Perkin Transactions 2 (2001), 2000, # 8, p. 1639 - 1644

  摘要：

  DOI：
• 作为产物：
  描述：

  DL-高半胱氨酸 在 盐酸 、 sodium perchlorate 、 sodium nitrite 作用下， 以100%的产率得到S-nitroso-homocysteine
  参考文献：
  名称：

  S-亚硝基硫醇形成对同型半胱氨酸毒性的调节：一种机制方法

  摘要：

  据报道，高半胱氨酸 (HCYSH) 代谢转化为高半胱氨酸硫内酯 (HTL) 是 HCYSH 发病的主要原因。假设通过 S-亚硝化抑制 HCYSH 的硫醇基团将阻止其代谢转化为 HTL。研究了 HCYSH 和亚硝酸反应生成S-亚硝基高半胱氨酸 (HCYSNO)的动力学、反应动力学和机制，在温和到高酸性的 pH 值下进行。此的Transnitrosation非蛋白形成由氨基酸小号还在磷酸盐缓冲液中在生理 pH 值 7.4 下研究了 - 亚硝基谷胱甘肽 (GSNO)。在这两种情况下，HCYSNO 都是定量形成的。发现铜离子具有双重作用，催化 HCYSNO 的形成速率及其分解速率。在过渡金属离子螯合剂的存在下，HCYSNO 在 pH 7.4 下非常稳定，半衰期为 198 小时。通过形成更强大的亚硝化剂、亚硝基阳离子 (NO + ) 和三氧化二氮 (N 2 O 3 ) ，亚硝酸发生亚硝化作用。在高酸性环境中，发现NO

  DOI：

  10.1021/jp103679v

文献信息

• Modulation of Homocysteine Toxicity by <i>S</i>-Nitrosothiol Formation: A Mechanistic Approach
  作者：Moshood K. Morakinyo、Robert M. Strongin、Reuben H. Simoyi

  DOI：10.1021/jp103679v

  日期：2010.8.5

  thiolactone (HTL) has been reported as the major cause of HCYSH pathogenesis. It was hypothesized that inhibition of the thiol group of HCYSH by S-nitrosation will prevent its metabolic conversion to HTL. The kinetics, reaction dynamics, and mechanism of reaction of HCYSH and nitrous acid to produce S-nitrosohomocysteine (HCYSNO) was studied in mildly to highly acidic pHs. Transnitrosation of this non-protein-forming

  据报道，高半胱氨酸 (HCYSH) 代谢转化为高半胱氨酸硫内酯 (HTL) 是 HCYSH 发病的主要原因。假设通过 S-亚硝化抑制 HCYSH 的硫醇基团将阻止其代谢转化为 HTL。研究了 HCYSH 和亚硝酸反应生成S-亚硝基高半胱氨酸 (HCYSNO)的动力学、反应动力学和机制，在温和到高酸性的 pH 值下进行。此的Transnitrosation非蛋白形成由氨基酸小号还在磷酸盐缓冲液中在生理 pH 值 7.4 下研究了 - 亚硝基谷胱甘肽 (GSNO)。在这两种情况下，HCYSNO 都是定量形成的。发现铜离子具有双重作用，催化 HCYSNO 的形成速率及其分解速率。在过渡金属离子螯合剂的存在下，HCYSNO 在 pH 7.4 下非常稳定，半衰期为 198 小时。通过形成更强大的亚硝化剂、亚硝基阳离子 (NO + ) 和三氧化二氮 (N 2 O 3 ) ，亚硝酸发生亚硝化作用。在高酸性环境中，发现NO
• Sulfur-to-nitrogen transnitrosation: transfer of nitric oxide from S-nitroso compounds to diethanolamine and the role of intermediate sulfur-to-sulfur transnitrosation
  作者：Ahmed H Al-Mustafa、Helmut Sies、Wilhelm Stahl

  DOI：10.1016/s0300-483x(01)00388-2

  日期：2001.6

  S-Nitrosothiols are formed in vivo and are involved in NO signaling. We investigated the sulfur-to-nitrogen transnitrosation activity of S-nitrosocysteine. S-nitrosoglutathione, S-nitrosohomocysteine, S-nitrusocysteinylglycine and S-nitroso-N-acerylcysteine in their reaction with the secondary amine diethanolamine in vitro. The resulting N-nitrosodiethanolamine, a strong carcinogen. was formed in yields of up to 11% from S-nitrosocysteine and S-nitrosocysteinylglycine, whereas the transnitrosation activity of the other S-nitroso compounds was weak. However. the addition of L-cysteine to a solution of S-nitrosohomocysteine and diethanolamine accelerated the decomposition of S-nitrosohomocysteine and resulted in a significant formation of N-nitrosodiethanolamine accompanied by the intermediate generation of S-nitrosocysteine. Thus, reactive nitrosothiols can be formed from less reactive analogs via sulfur-to-sulfur transnitrosation. We suggest that this affects regulation of NO trafficking in vivo. The reaction provides an alternative mechanism fur the generation of carcinogenic N-nitroso derivatives. (C) 2001 Elsevier Science Ireland Ltd. All rights reserved.
• Mechanism-Based Triarylphosphine-Ester Probes for Capture of Endogenous RSNOs
  作者：Uthpala Seneviratne、Luiz C. Godoy、John S. Wishnok、Gerald N. Wogan、Steven R. Tannenbaum

  DOI：10.1021/ja401565w

  日期：2013.5.22

  Nitrosothiols (RSNOs) have been proposed as important intermediates in nitric oxide (NO center dot) metabolism, storage, and transport as well as mediators in numerous NO. signaling pathways. RSNO levels are finely regulated, and dysregulation is associated with the etiology of several pathologies. Current methods for RSNO quantification depend on indirect assays that limit their overall specificity and reliability. Recent developments of phosphine-based chemical probes constitute a promising approach for the direct detection of RSNOs. We report here results from a detailed mechanistic and kinetic study for trapping RSNOs by three distinct phosphine probes, including structural identification of novel intermediates and stability studies under physiological conditions. We further show that a triarylphosphine-thiophenyl ester can be used in the absolute quantification of endogenous GSNO in several cancer cell lines, while retaining the elements of the SNO functional group, using an LC-MS-based assay. Finally, we demonstrate that a common product ion (m/z = 309.0), derived from phosphine RSNO adducts, can be used for the detection of other low-molecular weight nitrosothiols (LMW-RSNOs) in biological samples. Collectively, these findings establish a platform for the phosphine ligation-based, specific and direct detection of RSNOs in biological samples, a powerful tool for expanding the knowledge of the biology and chemistry of NO center dot-mediated phenomena.
• Holmes, Anthony J.; Williams, D. Lyn H., Journal of the Chemical Society. Perkin Transactions 2 (2001), 2000, # 8, p. 1639 - 1644
  作者：Holmes, Anthony J.、Williams, D. Lyn H.

  DOI：——

  日期：——