3-ethoxy-6-(3-hydroxypropyl)cyclohex-2-enone | 871927-35-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-ethoxy-6-(3-hydroxypropyl)cyclohex-2-enone
• 英文别名: 3-ethoxy-6-(3-hydroxypropyl)cyclohex-2-en-1-one
• CAS: 871927-35-4
• 化学式: C₁₁H₁₈O₃
• 分子量: 198.262
• InChiKey: ANMZPHJWJAMSJZ-UHFFFAOYSA-N

物化性质

• 沸点：
  349.0±35.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-ethoxy-6-(3-hydroxypropyl)cyclohex-2-enone 、 D-生物素 在 N,N'-二环己基碳二亚胺 作用下， 生成
  参考文献：
  名称：

  Sulfenic acid-reactive compounds and their methods of synthesis

  摘要：

  本发明提供了I式化合物：其中：R1是标记（例如，可检测的基团；抗肿瘤剂）；L存在或不存在，当存在时是连接基团；x代表1至10的整数；或其药学上可接受的盐。该化合物可用于识别蛋白质中的半胱氨酸磺酸和监测蛋白质和细胞中的氧化损伤等方面。

  公开号：

  US07294748B2
• 作为产物：
  描述：

  (+/-)-6-{3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]propyl}-3-ethoxy-2-cyclohexen-1-one 在 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以100%的产率得到3-ethoxy-6-(3-hydroxypropyl)cyclohex-2-enone
  参考文献：
  名称：

  Sulfenic acid-reactive compounds and their methods of synthesis

  摘要：

  本发明提供了I式化合物：其中：R1是标记（例如，可检测的基团；抗肿瘤剂）；L存在或不存在，当存在时是连接基团；x代表1至10的整数；或其药学上可接受的盐。该化合物可用于识别蛋白质中的半胱氨酸磺酸和监测蛋白质和细胞中的氧化损伤等方面。

  公开号：

  US07294748B2

文献信息

• Unbiased Detection of Cysteine Sulfenic Acid by 473 nm Photodissociation Mass Spectrometry: Toward Facile <i>In Vivo</i> Oxidative Status of Plasma Proteins
  作者：Jean-Valery Guillaubez、Delphine Pitrat、Yann Bretonnière、Jérôme Lemoine、Marion Girod

  DOI：10.1021/acs.analchem.0c04484

  日期：2021.2.9

  Cysteine (Cys) is prone to diverse post-translational modifications in proteins, including oxidation into sulfenic acid (Cys-SOH) by reactive oxygen species generated under oxidative stress. Detection of low-concentration and metastable Cys-SOH within complex biological matrices is challenging due to the dynamic concentration range of proteins in the samples. Herein, visible laser-induced dissociation (LID) implemented in a mass spectrometer was used for streamlining the detection of Cys oxidized proteins owing to proper derivatization of Cys-SOH with a chromophore tag functionalized with a cyclohexanedione group. Once grafted, peptides undergo a high fragmentation yield under LID, leading concomitantly to informative backbone ions and to a chromophore reporter ion. Seventy-nine percent of the Cys-containing tryptic peptides derived from human serum albumin and serotransferrin tracked by parallel reaction monitoring (PRM) were detected as targets subjected to oxidation. These candidates as well as Cys-containing peptides predicted by in silico trypsin digestion of five other human plasma proteins were then tracked in real plasma samples to pinpoint the endogenous Cys-SOH subpopulation. Most of the targeted peptides were detected in all plasma samples by LID-PRM, with significant differences in their relative amounts. By eliminating the signal of interfering co-eluted compounds, LID-PRM surpasses conventional HCD (higher-energy collisional dissociation)-PRM in detecting grafted Cys-SOH-containing peptides and allows now to foresee clinical applications in large human cohorts.

  半胱氨酸（Cys）在蛋白质中容易发生多种翻译后修饰，包括在氧化应激作用下被活性氧氧化成亚硫酸（Cys-SOH）。由于样品中蛋白质的动态浓度范围较大，因此在复杂的生物基质中检测低浓度和易变的 Cys-SOH 具有挑战性。在本文中，由于 Cys-SOH 与环己二酮基团功能化的发色团标签进行了适当的衍生，质谱仪中的可见激光诱导解离（LID）被用于简化 Cys 氧化蛋白质的检测。一旦接枝，肽就会在 LID 条件下发生高碎裂，同时产生信息骨架离子和发色团报告离子。在通过平行反应监测（PRM）跟踪的人血清白蛋白和血清转铁蛋白中，有 79% 的含 Cys 的胰蛋白肽被检测为氧化目标。然后在真实血浆样本中跟踪这些候选肽以及通过对其他五种人体血浆蛋白的硅胰蛋白酶消化预测出的含Cys肽，以确定内源性Cys-SOH亚群。LID-PRM 在所有血浆样本中都检测到了大部分目标肽，但其相对含量存在显著差异。通过消除干扰共沉淀化合物的信号，LID-PRM 在检测含 Cys-SOH 的接枝肽方面超越了传统的 HCD（高能碰撞解离）-PRM，现在可以预见其在大量人体样本中的临床应用。
• Sulfenic acid-reactive compounds and their methods of synthesis and use in detection or isolation of sulfenic acid-containing compounds
  申请人：Poole B. Leslie

  公开号：US20060084173A1

  公开（公告）日：2006-04-20

  The present invention provides compounds of Formula I: wherein: R 1 is a label (e.g., a detectable groups; an anti-tumor agent)s; L is present or absent and when present is a linking group; and x represents an integer from 1 to 10; or a pharmaceutically acceptable salt thereof. the compounds are useful for, among other things, identifying cysteine sulfenic acids in proteins and monitoring oxidative damage in proteins and cells.

  本发明提供了I式化合物：其中：R1是标记（例如，可检测的基团；抗肿瘤剂）；L存在或不存在，当存在时为连接基团；x表示1至10的整数；或其药学上可接受的盐。该化合物可用于识别蛋白质中的半胱氨酸磺酸和监测蛋白质和细胞中的氧化损伤等方面。
• SULFENIC ACID-REACTIVE COMPOUNDS
  申请人：Poole B. Leslie

  公开号：US20080070261A1

  公开（公告）日：2008-03-20

  The present invention provides compounds of Formula I: wherein: R 1 is a label (e.g., a detectable groups; an anti-tumor agent)s; L is present or absent and when present is a linking group; and x represents an integer from 1 to 10; or a pharmaceutically acceptable salt thereof. the compounds are useful for, among other things, identifying cysteine sulfenic acids in proteins and monitoring oxidative damage in proteins and cells.

  本发明提供了I式化合物：其中：R1是标签（例如，可检测的基团；抗肿瘤剂）；L存在或不存在，当存在时是连接基团；x代表1到10的整数；或其药学上可接受的盐。该化合物可用于识别蛋白质中的半胱氨酸磺酚酸并监测蛋白质和细胞中的氧化损伤等方面。
• Method for detecting target compounds containing sulfenic acids using new reagents
  申请人：Wake Forest University Health Sciences

  公开号：US07803630B2

  公开（公告）日：2010-09-28

  The present invention provides compounds of Formula I: wherein: R1 is a label (e.g., a detectable groups; an anti-tumor agent)s; L is present or absent and when present is a linking group; and x represents an integer from 1 to 10; or a pharmaceutically acceptable salt thereof. the compounds are useful for, among other things, identifying cysteine sulfenic acids in proteins and monitoring oxidative damage in proteins and cells.

  本发明提供了式I的化合物：其中：R1是标签（例如，可检测的基团；抗肿瘤剂）；L存在或不存在，当存在时是连接基团；x代表1到10的整数；或其药学上可接受的盐。该化合物可用于识别蛋白质中的半胱氨酸磺酸和监测蛋白质和细胞的氧化损伤等方面。
• SULFENIC ACID-REACTIVE COMPOUNDS AND THEIR METHODS OF SYNTHESIS AND USE IN DETECTION OR ISOLATION OF SULFENIC ACID-CONTAINING COMPOUNDS
  申请人：Wake Forest University Health Sciences

  公开号：US20130288268A1

  公开（公告）日：2013-10-31

  The present invention provides compounds of Formula I: wherein: R 1 is a label (e.g., a detectable groups; an anti-tumor agent)s; L is present or absent and when present is a linking group; and x represents an integer from 1 to 10; or a pharmaceutically acceptable salt thereof. the compounds are useful for, among other things, identifying cysteine sulfenic acids in proteins and monitoring oxidative damage in proteins and cells.

  本发明提供了I式化合物：其中：R1是标记（例如，可检测的基团；抗肿瘤剂）；L存在或不存在，当存在时是连接基团；x代表1到10的整数；或其药学上可接受的盐。该化合物可用于识别蛋白质中的半胱氨酸磺酸和监测蛋白质和细胞的氧化损伤等方面。