S-nitroso-cysteinylglycine | 162758-33-0

• 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: S-nitroso-cysteinylglycine
• 英文别名: S-nitroso-L-cysteinylglycine；2-[[(2R)-2-amino-3-nitrososulfanylpropanoyl]amino]acetic acid
• CAS: 162758-33-0
• 化学式: C₅H₉N₃O₄S
• 分子量: 207.21
• InChiKey: UOHAKHBEJRPHQZ-VKHMYHEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.1
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  147
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  二乙醇胺 、 S-nitroso-cysteinylglycine 以 phosphate buffer 为溶剂， 反应 1.0h， 生成 二乙醇亚硝胺
  参考文献：
  名称：

  Sulfur-to-nitrogen transnitrosation: transfer of nitric oxide from S-nitroso compounds to diethanolamine and the role of intermediate sulfur-to-sulfur transnitrosation

  摘要：

  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.

  DOI：

  10.1016/s0300-483x(01)00388-2
• 作为产物：
  描述：

  H-半胱氨酸-甘氨酸-OH 在 N-(N-L-γ-谷氨酰基-S-亚硝基-L-半胱氨酰----甘氨酸 作用下， 以 水 为溶剂， 反应 0.17h， 生成 S-nitroso-cysteinylglycine
  参考文献：
  名称：

  移动质子与移动自由基：含半胱氨酸肽的自由基阳离子的气相单分子化学

  摘要：

  电喷雾电离 (ESI)、多级和高分辨率质谱实验的组合用于检查含有二肽和三肽的半胱氨酸自由基阳离子的气相裂解反应。两种不同的化学方法被用来形成自由基阳离子的初始群体，其中自由基位点位于不同的位置：（1）通过质子化的含 S-亚硝基半胱氨酸的肽的键均裂以硫为中心的半胱氨酰自由基；(2) α-碳骨架中心自由基通过 Siu 的反应序列 ( J. Am. Chem. Soc. 2008, 130, 7862)。这些区域特异性产生的自由基的断裂反应的比较表明，相邻残基的 α CH 与半胱氨酰基自由基之间可能发生氢原子转移 (HAT)。此外，使用准确的质量测量、氘标记以及与真实样品的比较，显示部分 N 端半胱氨酸残基的新损失会产生质子化、截短的 N-甲酰基肽（偶电子 x ñ离子）。对自由基阳离子 [GCG] .+进行 DFT 计算以检查：具有不同自由基和质子化位点的异构体的相对稳定性；与四个可能的自由基位点

  DOI：

  10.1016/j.jasms.2010.01.027

文献信息

• Mobile protons versus mobile radicals: Gas-phase unimolecular chemistry of radical cations of cysteine-containing peptides
  作者：Adrian K. Y. Lam、Victor Ryzhov、Richard A. J. O’Hair

  DOI：10.1016/j.jasms.2010.01.027

  日期：2010.8.1

  electrospray ionization (ESI), multistage, and high-resolution mass spectrometry experiments are used to examine the gas-phase fragmentation reactions of radical cations of cysteine containing di- and tripeptides. Two different chemical methods were used to form initial populations of radical cations in which the radical sites were located at different positions: (1) sulfur-centered cysteinyl radicals via bond

  电喷雾电离 (ESI)、多级和高分辨率质谱实验的组合用于检查含有二肽和三肽的半胱氨酸自由基阳离子的气相裂解反应。两种不同的化学方法被用来形成自由基阳离子的初始群体，其中自由基位点位于不同的位置：（1）通过质子化的含 S-亚硝基半胱氨酸的肽的键均裂以硫为中心的半胱氨酰自由基；(2) α-碳骨架中心自由基通过 Siu 的反应序列 ( J. Am. Chem. Soc. 2008, 130, 7862)。这些区域特异性产生的自由基的断裂反应的比较表明，相邻残基的 α CH 与半胱氨酰基自由基之间可能发生氢原子转移 (HAT)。此外，使用准确的质量测量、氘标记以及与真实样品的比较，显示部分 N 端半胱氨酸残基的新损失会产生质子化、截短的 N-甲酰基肽（偶电子 x ñ离子）。对自由基阳离子 [GCG] .+进行 DFT 计算以检查：具有不同自由基和质子化位点的异构体的相对稳定性；与四个可能的自由基位点
• Bannenberg; Xue; Engman, Journal of Pharmacology and Experimental Therapeutics, 1995, vol. 272, # 3, p. 1238 - 1245
  作者：Bannenberg、Xue、Engman、Cotgreave、Moldeus、Ryrfeldt

  DOI：——

  日期：——
• 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.
• 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.