3-mercapto-S-nitroso-1,2-propanediol | 152829-62-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-mercapto-S-nitroso-1,2-propanediol
• 英文别名: S-nitrosothioglycerol；S-nitroso-1-thioglycerol；3-Nitrososulfanylpropane-1,2-diol
• CAS: 152829-62-4
• 化学式: C₃H₇NO₃S
• 分子量: 137.159
• InChiKey: LHDUMLDMQBPCKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  95.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  DL-青霉胺 、 3-mercapto-S-nitroso-1,2-propanediol 以 水 为溶剂， 生成
  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：

  1-硫代甘油 在 盐酸 、 硫酸 、 sodium nitrite 作用下， 以 甲醇 为溶剂， 生成 3-mercapto-S-nitroso-1,2-propanediol
  参考文献：
  名称：

  Synthesis and kinetics of decomposition of some novel S-nitrosothiols

  摘要：

  S-亚硝基巯基物质2-乙酰胺基-2-脱氧-S-亚硝基-1-硫基-β-D-葡萄糖吡喃糖3,4,6-三乙酸酯（GPSNO）和S-亚硝基-N-氨基-D，L-青霉胺（SNCP）通过相应巯基的S-亚硝化反应合成，分离并进行了全面的表征。从1-巯基甘油中获得的亚硝基巯基物质（TGSNO）为红色胶状液体，在室温下迅速分解，因此没有进行表征。GPSNO的分解动力学表明存在一个令人惊讶的大热途径与Cu2+ / RS-催化反应重叠。结果强烈表明，产物二硫化物形成了Cu2+络合物（有一些光谱证据支持），从而导致了该途径的不完全转化。抗坏血酸也作为Cu2+还原剂。另一个S-亚硝基糖，S-亚硝基-1-硫基-β-D-葡萄糖（SNTG），从生成并现场使用的溶液中表现出非常相似的行为。TGSNO的分解显示出诱导期，表明慢速初始生成Cu+（真正的催化剂）正在发生。还存在一个显着的替代途径（类似于GPSNO发现的途径），其中速率似乎与[Cu2+]无关，但非常不寻常的是，该途径可以通过在反应开始时或稍后加入EDTA来有效地停止。提出了反应方案来解释这些异常的反应特性。关键词：S-亚硝基巯基物质，一氧化氮，抗坏血酸，铜催化。

  DOI：

  10.1139/v99-026

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。
• S-nitrosothiol-generating skin dressings
  申请人：Insense Limited

  公开号：US09345804B2

  公开（公告）日：2016-05-24

  The present disclosure relates to a skin dressing adapted, on activation, to generate one or more S-nitrosothiols by reaction between a thiol and a nitrite salt in the skin dressing for delivery of nitric oxide to a body site. The skin dressing comprises a source of Cu2+, Zn2+ and/or Fe2+ ions.

  本公开涉及一种皮肤敷料，当激活时，通过皮肤敷料中硫醇和亚硝酸盐之间的反应生成一种或多种S-亚硝基硫醇，以向身体部位输送一氧化氮。该皮肤敷料包括Cu2+，Zn2+和/或Fe2+离子的来源。
• 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：——
• 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.
• Synthesis and kinetics of decomposition of some novel <i>S-</i>nitrosothiols
  作者：Andrew P Munro、D Lyn H. Williams

  DOI：10.1139/v99-026

  日期：1999.6.1

  TheS-nitrosothiols 2-acetamido-2-deoxy-S-nitroso-1-thio-β-D-glucopyranose 3,4,6-triacetate (GPSNO) and S-nitroso-N-carbamyl-D,L-penicillamine (SNCP) were synthesized by S-nitrosation of the corresponding thiols, isolated, and fully characterized. The nitrosothiol (TGSNO) from 1-thioglycerol was obtained as a red gelatinous liquid, which decomposed rapidly at room temperature and so was not characterized. The kinetics of decomposition of GPSNO showed that there is a surprisingly large thermal pathway overlaid with a Cu²⁺/RS^- catalyzed reaction. The results strongly suggest that the product disulfide complexes Cu²⁺ (for which there is some spectral evidence), leading to incomplete conversion by that route. Ascorbate also acts as a Cu²⁺ reductant. Another S-nitroso sugar, S-nitroso-1-thio-β-D-glucose (SNTG), behaved very similarly from solutions generated and used in situ. The decomposition of TGSNO shows induction periods suggesting that slow initial generation of Cu⁺ (the true catalyst) is taking place. There appears to be also a significant alternative pathway (analogous to that found for GPSNO), where the rate appears to be independent of [Cu²⁺], but very unusually this pathway is effectively halted by addition of EDTA either at the start of the reaction or at a later time. Reaction schemes are put forward to account for these unusual reaction characteristics.Key words: S-nitrosothiols, nitric oxide, ascorbate, copper catalysis.

  S-亚硝基巯基物质2-乙酰胺基-2-脱氧-S-亚硝基-1-硫基-β-D-葡萄糖吡喃糖3,4,6-三乙酸酯（GPSNO）和S-亚硝基-N-氨基-D，L-青霉胺（SNCP）通过相应巯基的S-亚硝化反应合成，分离并进行了全面的表征。从1-巯基甘油中获得的亚硝基巯基物质（TGSNO）为红色胶状液体，在室温下迅速分解，因此没有进行表征。GPSNO的分解动力学表明存在一个令人惊讶的大热途径与Cu2+ / RS-催化反应重叠。结果强烈表明，产物二硫化物形成了Cu2+络合物（有一些光谱证据支持），从而导致了该途径的不完全转化。抗坏血酸也作为Cu2+还原剂。另一个S-亚硝基糖，S-亚硝基-1-硫基-β-D-葡萄糖（SNTG），从生成并现场使用的溶液中表现出非常相似的行为。TGSNO的分解显示出诱导期，表明慢速初始生成Cu+（真正的催化剂）正在发生。还存在一个显着的替代途径（类似于GPSNO发现的途径），其中速率似乎与[Cu2+]无关，但非常不寻常的是，该途径可以通过在反应开始时或稍后加入EDTA来有效地停止。提出了反应方案来解释这些异常的反应特性。关键词：S-亚硝基巯基物质，一氧化氮，抗坏血酸，铜催化。