N-acetyl-D,L-penicillamine disulfide | 67809-84-1

• 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: N-acetyl-D,L-penicillamine disulfide
• 英文别名: 3,3'-dithiobis[N-acetyl-Valine；2-acetamido-3-[(1-acetamido-1-carboxy-2-methylpropan-2-yl)disulfanyl]-3-methylbutanoic acid
• CAS: 67809-84-1
• 化学式: C₁₄H₂₄N₂O₆S₂
• 分子量: 380.486
• InChiKey: TYARMXWNXXYBMN-UHFFFAOYSA-N

物化性质

• 沸点：
  679.5±55.0 °C(Predicted)
• 密度：
  1.314±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  183
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  S-亚硝基-N-乙酰-DL-青霉胺 在 铜 作用下， 以 水 为溶剂， 生成 N-acetyl-D,L-penicillamine disulfide
  参考文献：
  名称：

  Metal ion catalysis in nitrosothiol (RSNO) decomposition

  摘要：

  在微量 Cu2+ 和 Fe2+ 的催化下，S-亚硝基-N-乙酰基 D,L-青霉胺（SNAP）（一种 NO 供体药物）分解生成二硫化物和 NO。

  DOI：

  10.1039/c39930001758

文献信息

• An unusually stable thionitrite from N-acetyl-D,L-penicillamine; X-ray crystal and molecular structure of 2-(acetylamino)-2-carboxy-1,1-dimethylethyl thionitrite
  作者：Lamar Field、Robert V. Dilts、Ramanathan Ravichandran、P. Galen Lenhert、Gary E. Carnahan

  DOI：10.1039/c39780000249

  日期：——

  N-Acetyl-D,L-penicillamine (1) was converted by HNO2 into a thionitrite (3) which was stable as a solid and atypically so even in solution; X-ray structural parameters are given for (3), and both homolytic and heterolytic reactions are described.

  HNO 2将N-乙酰基-D，L-青霉胺（1）转化为亚硝酸盐（3），该亚硝酸盐作为固体是稳定的，并且即使在溶液中也是如此。给出了（3）的X射线结构参数，并且描述了均溶反应和杂溶反应。
• The mechanism of nitric oxide formation from S-nitrosothiols (thionitrites)
  作者：D. Lyn H. Williams

  DOI：10.1039/cc9960001085

  日期：——

  S-Nitrosothiols (RSNO) are easily made by electrophilic nitrosation of thiols and are a convenient source of nitric oxide. Reaction occurs readily (in many cases) in aqueous buffer at pH 7.4 to give in addition the corresponding disulfide RSSR. If oxygen is not rigorously excluded from the solution, then the nitric oxide is converted quantitatively to nitrite ion, whereas in the absence of oxygen nitric oxide can be detected using a commercial NO-probe. Reaction, however, only occurs (apart from the photochemical pathway) if Cu2+ is present. There is often enough Cu2+ in the distilled water–buffer components to bring about reaction, but decomposition is halted if Cu2+ is complexed with EDTA. Experiments with the specific Cu+ chelator neocuproine however show that the true effective reagent is Cu+, formed by reduction of Cu2+ with thiolate ion. Kinetic experiments show that the most reactive nitrosothiols are those which can coordinate bidentately with Cu+, and there is a wide range of reactivity amongst the structures studied. Reactivity is crucially dependent on the concentrations of Cu2+ and RS–.Reaction also occurs, although somewhat more slowly, if the source of copper is the CuII complex with the tripeptide diglycyl-L-histidine (GGH) or as the CuII complex with human serum albumin (HSA). This allows the possibility that nitrosothiols could in principle generate nitric oxide in vivo using the naturally occurring sources of CuII.Rapid exchange of the NO-group in RSNO with thiols occurs, again in aqueous buffer at pH 7.4. This reaction has been established as a nucleophilic substitution reaction by the thiolate ion at the nitroso nitrogen atom.The implications of these results with regard to possible involvement of nitrosothiols in vivo are discussed.

  S-亚硝基硫醇 (RSNO) 通过硫醇的电亲核亚硝化反应容易制备，并且是氮氧化物的便捷来源。在 pH 7.4 的水缓冲液中（在许多情况下），反应会迅速发生，从而生成相应的二硫化物 RSSR。如果溶液中没有严格排除氧气，则一氧化氮会定量转化为亚硝酸盐离子，而在缺氧的情况下，可以通过商业一氧化氮探针检测到一氧化氮。然而，反应仅在存在 Cu2+ 的情况下发生（除了光化学途径）。通常在蒸馏水-缓冲液成分中有足够的 Cu2+ 促使反应发生，但如果 Cu2+ 与 EDTA 形成络合物，则分解会被阻止。然而，使用特定的 Cu+ 螯合剂新铜碱（neocuproine）进行的实验表明，真正的有效试剂是 Cu+，它是通过硫醇阴离子还原 Cu2+ 形成的。动力学实验表明，反应性最强的亚硝基硫醇是那些能够与 Cu+ 形成二配位的分子，而且在所研究的结构中反应性存在广泛的变异。反应性在很大程度上依赖于 Cu2+ 和 RS– 的浓度。当铜的来源是与三肽二甘氨基-L-组氨酸 (GGH) 的 CuII 络合物或与人血清白蛋白 (HSA) 的 CuII 络合物时，反应也会发生，虽然速度较慢。这使得亚硝基硫醇在原则上能够利用天然存在的 CuII 产生体内的一氧化氮。RSNO 中 NO 基团与硫醇之间的快速交换同样发生，在 pH 7.4 的水缓冲液中进行。此反应已被确定为硫醇阴离子在亚硝基氮原子上的亲核取代反应。讨论了这些结果对于亚硝基硫醇在体内可能参与的影响。
• Synthesis and nitric oxide releasing properties of novel fluoro<i>S</i>-nitrosothiols
  作者：Yang Zhou、Jinyi Tan、Yuping Dai、Yanmin Yu、Qi Zhang、Mark E. Meyerhoff

  DOI：10.1039/c8cc08868c

  日期：——

  series of new fluoro S-nitrosothiols is reported as potential nitric oxide (NO) donors. A three-step synthesis and the NO releasing kinetic profiles of these species are presented. The stoichiometric release of NO, with the clean formation of corresponding disulfides, confirms that these new species can facilitate their application as NO donors for various applications including creating novel antimicrobial

  据报道，一系列新的氟 S-亚硝基硫醇是潜在的一氧化氮 (NO) 供体。介绍了这些物质的三步合成和 NO 释放动力学曲线。NO 的化学计量释放以及相应二硫化物的干净形成，证实这些新物种可以促进它们作为 NO 供体用于各种应用，包括创建新型抗菌和抗血栓的基于含氟聚合物的医疗设备。
• The pentacyanonitrosylferrate ion—V. The course of the reactions of nitroprusside with a range of thiols
  作者：Anthony R. Butler、Adrianne M. Calsy-Harrison、Christopher Glidewell、Poul E. Sørensen

  DOI：10.1016/s0277-5387(00)81208-5

  日期：1988.1

  react with nitroprusside ([Fe(CN)5NO]2−, pentacyanonitrosylferrate (2−)) to give, via the intermediates [Fe(CN)5N(O)SR]3− and [Fe(CN)5NO]3−, the pentacoordinate iron(I) complex [Fe(CN)4NO]2−. The fate of this complex depends crucially upon the reaction conditions; in the presence of oxygen, [Fe(CN)4NO]2− can reform [Fe(CN)5NO]2− to give an effective stoichiometry of RS− to [Fe(CN)5NO]2− substantially

  硫醇RSH（RSH =网格，半胱氨酸，N-乙酰半胱氨酸，2-甲基半胱氨酸，N-乙酰基-2-甲基半胱氨酸，青霉胺，N-乙酰青霉胺和谷胱甘肽）与硝普盐（的[Fe（CN）反应5 NO] 2-，pentacyanonitrosylferrate（ 2-））经由中间体[Fe（CN）5 N（O）SR] 3-和[Fe（CN）5 NO] 3-生成五配位铁（I）络合物[Fe（CN）4 NO ] 2−。这种复合物的命运主要取决于反应条件。在氧的存在下，的[Fe（CN）4 NO] -2-可以改造的[Fe（CN）5 NO] 2-，得到RS的有效的化学计量-至[Fe（CN）5 NO] 2−实质上大于1：1。在无氧且化学计量比为1：1的情况下，[Fe（CN）4 NO] 2−遵循公认的途径生成[Fe（CN）6 ] 4−，Fe 2+和NO。在不存在氧的并用过量的RS的-配体，取代发生在的[Fe（CN）4 NO] 2-，得到先的[Fe（NO）2（SR）2
• 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：——