(S)-亚硝基-L-半胱氨酸乙酯 | 166667-89-6

• 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
• 中文名称: (S)-亚硝基-L-半胱氨酸乙酯
• 英文名称: (S)-nitroso-L-cysteine ethyl ester
• 英文别名: S-nitroso-L-cysteine ethyl ester；s-Nitroso-l-cysteine-ethyl-ester；ethyl (2R)-2-amino-3-nitrososulfanylpropanoate
• CAS: 166667-89-6
• 化学式: C₅H₁₀N₂O₃S
• 分子量: 178.212
• InChiKey: KVGDXUBJVIZGEX-BYPYZUCNSA-N

物化性质

• 沸点：
  259.6±50.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-亚硝基-L-半胱氨酸乙酯 在 铜 作用下， 以 水 为溶剂， 生成 L-胱氨酸二乙酯二盐酸盐
  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：

  L-半胱氨酸乙酯 在 N-甲基-N-亚硝基对甲苯磺酰胺 作用下， 以 乙醇 、 水 为溶剂， 生成 (S)-亚硝基-L-半胱氨酸乙酯
  参考文献：
  名称：

  Oh, Shirlene M. N. Y. F.; Williams, D. Lyn H., Journal of the Chemical Society. Perkin transactions II, 1989, p. 755 - 758

  摘要：

  DOI：

文献信息

• Nitrosation by alkyl nitrites. Part 6. Thiolate nitrosation
  作者：Hanif M. S. Patel、D. Lyn H. Williams

  DOI：10.1039/p29900000037

  日期：——

  differs significantly from the literature value. With simple alkyl nitrites (ethyl, isopentyl, isopropyl and t-butyl) steric effects appear to be the major influences in reactivity, whereas electron-withdrawing substituents in the 2-position greatly increase the rate constants. The reactions of 2,2,2-trichloroethyl nitrite were too fast to measure at all pH values, whereas the reaction of 2,2-dichloroethyl

  以下每种硫醇在25°C的水中在6-13的pH范围内与一定范围内的亚硝酸烷基酯反应，在溶液中生成相应的亚硝酸盐：L-半胱氨酸，N-乙酰基-L-半胱氨酸，L-半胱氨酸甲酯，L-半胱氨酸乙酯，谷胱甘肽和巯基乙酸。速率常数的pH依赖性清楚地表明，反应仅通过硫醇根阴离子RS –发生。对于Ñ乙酰基大号-半胱氨酸和巯基乙酸只有一个RS -物种是可能的和定量动力学分析产率p ķ一个RSH电离的值与文献值非常吻合。对于每种剩余的硫醇，可能有两个硫醇根离子（NH 2 RS –和NH 3 RS –），所有亚硝酸烷基酯的测得的速率常数通常跟随从公开的显微图中获得的总硫醇根离子浓度（作为pH的函数）。 p K a值。通过计算机将动力学结果拟合到浓度曲线的另一种方法是产生通常与文献值相吻合的微观p K a值。L-半胱氨酸是一个例外，其中测得的（p K a）D值（对于NH 2 -RSH→NH 2 RS –）与文献值明显
• Equilibrium and kinetics studies of transnitrosation between S-nitrosothiols and thiols
  作者：Kun Wang、Zhong Wen、Wei Zhang、Ming Xian、Jin-Pei Cheng、Peng George Wang

  DOI：10.1016/s0960-894x(00)00688-0

  日期：2001.2

  Using UV-vis spectrometrical measurements, equilibrium constants for NO transfer between S-nitroso-N-acetyl-penicillamine (SNAP) and different thiols as well as kinetic data for NO transfer from S-nitroso bovine serum albumin (BSANO) to thiols have been obtained, NO transfer from SNAP to other primary/secondary thiols are thermodynamically favorable, whereas other S-nitrosothiols exhibit similar NO transfer potential. The obtained Gibbs free energy, enthalpy and entropy data indicated that NO transfer reactions from SNAP to four thiols are exothermic with entropy loss. The kinetic behavior of BSANO/RSH transfer can be related to both the acidity of sulfhydryl group and the electronic structure in thiol. (C) 2001 Elsevier Science Ltd. All rights reserved.
• 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：——
• 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.
• Oh, Shirlene M. N. Y. F.; Williams, D. Lyn H., Journal of the Chemical Society. Perkin transactions II, 1989, p. 755 - 758
  作者：Oh, Shirlene M. N. Y. F.、Williams, D. Lyn H.

  DOI：——

  日期：——