S-nitroso-beta-mercaptosuccinic acid | 152829-60-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: S-nitroso-beta-mercaptosuccinic acid
• 英文别名: S-nitrosothiomalic acid；S-nitroso-b-mercaptosuccinic acid；2-nitrososulfanylbutanedioic acid
• CAS: 152829-60-2
• 化学式: C₄H₅NO₅S
• 分子量: 179.153
• InChiKey: UGKJHHFIYVQKNF-UHFFFAOYSA-N

物化性质

• 沸点：
  307.2±52.0 °C(Predicted)
• 密度：
  1.74±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  129
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  巯基丁二酸 、 S-nitroso-beta-mercaptosuccinic acid 以 水 为溶剂， 生成 3,4-dithia-hexane-1,2,5,6-tetracarboxylic acid
  参考文献：
  名称：

  The reaction of <i>S</i>-nitrosothiols with thiols at high thiol concentration

  摘要：

  Reactions of S-nitrosothiols (RSNO) with their corresponding thiols (RSH) present in a large excess (>20-fold) proceed readily to give the disulfide. Ammonia is formed together with some nitrite anion, and these constitute >90% of the "nitrogen" products. This is in marked contrast with the reaction at low thiol concentration, where nitric oxide is the major initial "nitrogen" product, which is rapidly converted in the presence of oxygen in water to nitrite anion. Also in marked contrast to the "low thiol concentration" reaction, the reaction at high thiol concentration is not affected by added Cu2+, nor by the metal-ion scavenger EDTA. Kinetically all reactions were excellent first-order processes, and the reactions were also strictly first order in thiol concentration. A large range of nitrosothiols were studied and the generality of the reaction established. Some reactions of RSNO with other thiols (R'SH) were examined and the results readily interpreted in terms of a prior rapid equilibrium transnitrosation. The pH dependence for the reaction of S-nitrosocysteine with cysteine clearly showed that the reactive species is the cysteine thiolate anion. The results are discussed along with those of two other recent reports of these reactions, in terms of thiolate attack initially at the nitroso nitrogen atom, and subsequently at sulfur atoms, eliminating RSSR and yielding hydroxylamine, which is rapidly reduced by thiolate ion to ammonia. The results are also discussed in connection with the release of NO from nitrosothiols and with the important biological consequences, both for the in vivo reactions of NO and for the potential of nitrosothiols as NO-releasing drugs for medical use.

  DOI：

  10.1139/cjc-76-6-789
• 作为产物：
  描述：

  巯基丁二酸 在 高氯酸 、 nitrosyl bromide 作用下， 以 水 为溶剂， 生成 S-nitroso-beta-mercaptosuccinic acid
  参考文献：
  名称：

  某些含硫醇的氨基酸和其他硫醇进行S-亚硝化的动力学和机理

  摘要：

  已在25°C的水中测定了半胱氨酸，半胱氨酸甲酯，N-乙酰半胱氨酸，青霉素，N-乙酰青霉胺，谷胱甘肽，巯基乙酸和巯基琥珀酸的S-亚硝化的速率常数。所有非常活泼，并显示酸和亲核（CL - ，溴-和SCN - ）催化。对于反应性更高的硫醇，通过H 2 NO 2 +进行反应的速率常数以及通过ClNO进行反应的速率常数的相似性表明，这些反应是受控的。ClNO反应的极限速率常数（约1×107 dm 3 s –1）与一系列脂肪胺的亚硝化非常相似。N-乙酰基衍生物和谷胱甘肽的高反应性可以通过羰基的氧原子在硫上形成的正电荷的内部稳定来解释，所述羰基的氧原子涉及六元环结构。对于较高[RSH]时反应性更高的硫醇，ClNO，BrNO或ONSCN的形成速率趋于成为速率限制。得出的XNO形成速率常数以及XNO水解的速率常数合理地一致，并且还给出了XNO形成的平衡常数的值，该值与直接测量的文献值相符。

  DOI：

  10.1039/p29880000513

文献信息

• Stable NO-delivering compounds
  申请人：Duke University

  公开号：US06359167B2

  公开（公告）日：2002-03-19

  Disclosed are novel NO-releasing compounds which comprise a stabilized S-nitrosyl group and a free alcohol or a free thiol group. Also disclosed is a method of preparing the NO-releasing compounds. The method comprises reacting a polythiol or a thioalcohol with a nitrosylating agent. Also disclosed are medical devices coated with the disclosed compounds, methods of delivering NO to treatments sites in a subject by utilizing the medical devices and methods of sterilizing surfaces.

  本发明揭示了一种新型的NO释放化合物，其包括稳定的S-亚硝基基团和自由醇或自由硫醇基团。还揭示了一种制备NO释放化合物的方法。该方法包括将多硫醇或硫醇与亚硝化剂反应。还揭示了用所述化合物涂覆的医疗器械，通过利用医疗器械将NO输送到受试者的治疗部位的方法以及表面消毒的方法。
• Askew, Stuart C.; Barnett, D. Jonathan; McAninly, John, Journal of the Chemical Society. Perkin transactions II, 1995, # 4, p. 741 - 746
  作者：Askew, Stuart C.、Barnett, D. Jonathan、McAninly, John、Williams, D. Lyn H.

  DOI：——

  日期：——
• Dix, Leslie R.; Williams, D. Lyn H., Journal of the Chemical Society. Perkin transactions II, 1984, # 1, p. 109 - 112
  作者：Dix, Leslie R.、Williams, D. Lyn H.

  DOI：——

  日期：——
• Barnett, D.Jonathan; Rios, Ana; Williams, D. Lyn H., Journal of the Chemical Society. Perkin transactions II, 1995, # 7, p. 1279 - 1282
  作者：Barnett, D.Jonathan、Rios, Ana、Williams, D. Lyn H.

  DOI：——

  日期：——
• The reaction of &lt;i&gt;S&lt;/i&gt;-nitrosothiols with thiols at high thiol concentration
  作者：Andrew P. Dicks、E. Li、Andrew P. Munro、Helen R. Swift、D. Lyn H. Williams

  DOI：10.1139/cjc-76-6-789

  日期：——

  Reactions of S-nitrosothiols (RSNO) with their corresponding thiols (RSH) present in a large excess (>20-fold) proceed readily to give the disulfide. Ammonia is formed together with some nitrite anion, and these constitute >90% of the "nitrogen" products. This is in marked contrast with the reaction at low thiol concentration, where nitric oxide is the major initial "nitrogen" product, which is rapidly converted in the presence of oxygen in water to nitrite anion. Also in marked contrast to the "low thiol concentration" reaction, the reaction at high thiol concentration is not affected by added Cu2+, nor by the metal-ion scavenger EDTA. Kinetically all reactions were excellent first-order processes, and the reactions were also strictly first order in thiol concentration. A large range of nitrosothiols were studied and the generality of the reaction established. Some reactions of RSNO with other thiols (R'SH) were examined and the results readily interpreted in terms of a prior rapid equilibrium transnitrosation. The pH dependence for the reaction of S-nitrosocysteine with cysteine clearly showed that the reactive species is the cysteine thiolate anion. The results are discussed along with those of two other recent reports of these reactions, in terms of thiolate attack initially at the nitroso nitrogen atom, and subsequently at sulfur atoms, eliminating RSSR and yielding hydroxylamine, which is rapidly reduced by thiolate ion to ammonia. The results are also discussed in connection with the release of NO from nitrosothiols and with the important biological consequences, both for the in vivo reactions of NO and for the potential of nitrosothiols as NO-releasing drugs for medical use.