2-oxo-1-oxa-4-thiaspiro <4.4> nonan-3-ylacetic acid | 134767-82-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代缩醛
• 英文名称: 2-oxo-1-oxa-4-thiaspiro <4.4> nonan-3-ylacetic acid
• 英文别名: (2-oxo-1-oxa-4-thia-spiro[4.4]non-3-yl)-acetic acid；(2-oxo-1-oxa-4-thiaspiro[4.4]non-3-yl)acetic acid；2-{2-Oxo-1-oxa-4-thiaspiro[4.4]nonan-3-yl}acetic acid；2-(2-oxo-1-oxa-4-thiaspiro[4.4]nonan-3-yl)acetic acid
• CAS: 134767-82-1
• 化学式: C₉H₁₂O₄S
• 分子量: 216.258
• InChiKey: KZPNJNAEUVMDMA-UHFFFAOYSA-N

物化性质

• 熔点：
  93 °C
• 沸点：
  506.2±35.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  88.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-oxo-1-oxa-4-thiaspiro <4.4> nonan-3-ylacetic acid 在 叠氮磷酸二苯酯 、 三乙胺 作用下， 以 苯 为溶剂， 反应 2.0h， 生成 3-Isocyanatomethyl-1-oxa-4-thia-spiro[4.4]nonan-2-one
  参考文献：
  名称：

  从巯基琥珀酸方便地合成异半胱氨酸

  摘要：

  摘要 该通讯描述了一种方便的两步法，用于从巯基琥珀酸以 49% 的产率制备 S-苄基-d,1-异半胱氨酸。

  DOI：

  10.1080/00397919108020820
• 作为产物：
  描述：

  巯基丁二酸 、 环戊酮 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 8.0h， 以71%的产率得到2-oxo-1-oxa-4-thiaspiro <4.4> nonan-3-ylacetic acid
  参考文献：
  名称：

  控制细胞内大环化对蛋白酶活性的成像

  摘要：

  地面记者：在特定酶的控制下，谷胱甘肽（GSH）还原后，在活细胞中分子内大环化反应高效发生。在细胞中合成的大环产物（表示为蓝环）自组装成纳米颗粒，聚集并保留在酶位置附近的位置，以报告活细胞中的局部蛋白水解活性。

  DOI：

  10.1002/anie.201006140

文献信息

• New isocysteine building blocks and chemoselective peptide ligation
  作者：Christian Dose、Oliver Seitz

  DOI：10.1039/b309235f

  日期：——

  Boc-, Fmoc- and Cbz-protected isocysteine building blocks were prepared by a concise three-step procedure starting from thiomalic acid. The use of Boc/Trt-protected isocysteine provided convenient access to isocysteinyl peptides that allow the chemoselective ligation of unprotected peptide fragments in water. The pH-dependency of the isocysteine-mediated ligation was compared with that of cysteine-mediated native chemical ligation.

  以硫代苹果酸为起点，通过简洁的三步法制备出 Boc、Fmoc 和 Cbz 保护的异半胱氨酸构筑模块。使用 Boc/Trt 保护的异半胱氨酸可以方便地获得异半胱氨酸肽，从而可以在水中对未受保护的肽片段进行化学选择性连接。比较了异半胱氨酸介导的连接与半胱氨酸介导的原生化学连接的 pH 依赖性。
• Selective Preparation of β-Monoesters of Mercaptosuccinic Acid with Acid or Base Labile Sulfur Protecting Groups and Esters
  作者：Linda M. Gustavson、David S. Jones、Jeffrey S. Nelson、Ananthachari Srinivasan

  DOI：10.1080/00397919108020819

  日期：1991.1

  Abstract Sulfur protected mercaptosuccinic acid β-monoesters were prepared by two complimentary methods. Alkylation of enolates of hemithioacetal protected mercaptoacetic acid with t-butyl bromoacetate directly provides the base stable t-butyl esters 2a and 2b. Alternatively, protection of the α-carboxylate and thiol as an oxathiolone permits the preparation of the base labile S-acyl protected mercaptosuccinic

  摘要 通过两种互补的方法制备了硫保护的巯基琥珀酸β-单酯。半硫代缩醛保护的巯基乙酸的烯醇化物与溴乙酸叔丁酯的烷基化直接提供碱稳定的叔丁酯 2a 和 2b。或者，将α-羧酸盐和硫醇作为氧杂硫酮进行保护允许制备碱不稳定的S-酰基保护的巯基琥珀酸酯2c和2d。
• A Convenient Synthesis of Isocysteine from Mercaptosuccinic Acid
  作者：Linda M. Gustavson、Ananthachari Srinivasan

  DOI：10.1080/00397919108020820

  日期：1991.1

  Abstract This communication describes a convenient, two step procedure for the preparation of S-benzyl-d,1-isocysteine from mercaptosuccinic acid in 49% yield.

  摘要 该通讯描述了一种方便的两步法，用于从巯基琥珀酸以 49% 的产率制备 S-苄基-d,1-异半胱氨酸。
• Single nucleotide specific detection of DNA by native chemical ligation of fluorescence labeled PNA-probes
  作者：Christian Dose、Oliver Seitz

  DOI：10.1016/j.bmc.2007.04.059

  日期：2008.1

  DNA-directed chemical ligations provide the opportunity to diagnose DNA sequences with very high sequence specificity. Fluorescent labels have been attached to reactive probes to enable the homogeneous detection of DNA and RNA. However, it has frequently been found that the attachment of fluorescent labels results in decreases of ligation fidelity. Herein we describe the development of a fluorogenic ligation reaction that provides for 10(2)-fold to perfect sequence selectivity. The reaction is based on the isocysteine-mediated native chemical PNA ligation. It is shown that DNA-induced rate accelerations of similar to 43.000-fold can be obtained through subtle variations of the ligation conditions. PNA-thioesters and isocysteine-PNA conjugates were labeled with FAM and TMR fluorophores, respectively. For gaining rapid synthetic access, a convenient on-resin labeling approach was developed. A new PNA monomer featuring an Alloc-protected lysine side chain was synthesized and coupled in solid-phase PNA synthesis. In the event of a ligation reaction the two fluorophores are brought into proximity. It is shown that fluorescence resonance energy transfer provides a positive fluorescence signal which is specific for product formation rather than for loss of starting materials. Single base mutations can be detected within minutes and with very high sequence selectivity at optimized conditions. (C) 2007 Elsevier Ltd. All rights reserved.
• Controlling Intracellular Macrocyclization for the Imaging of Protease Activity
  作者：Deju Ye、Gaolin Liang、Man Lung Ma、Jianghong Rao

  DOI：10.1002/anie.201006140

  日期：2011.3.1

  ground: An intramolecular macrocyclization reaction took place highly efficiently in live cells under the control of a specific enzyme and reduction by glutathione (GSH; see picture). Macrocyclic products (represented as blue rings) synthesized in cells self‐assembled into nanoparticles aggregated and retained at the site near the enzyme location to report local proteolytic activity in live cells.

  地面记者：在特定酶的控制下，谷胱甘肽（GSH）还原后，在活细胞中分子内大环化反应高效发生。在细胞中合成的大环产物（表示为蓝环）自组装成纳米颗粒，聚集并保留在酶位置附近的位置，以报告活细胞中的局部蛋白水解活性。