2-hydroxy-hexa-2,4-dienoic acid | 84363-48-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-hydroxy-hexa-2,4-dienoic acid
• 英文别名: HDD；2-Hydroxyhex-4-enoic acid
• CAS: 84363-48-4
• 化学式: C₆H₁₀O₃
• 分子量: 130.144
• InChiKey: UPXKHUBIJAUPSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  Hydroxy-acetic acid 1-methyl-allyl ester 在 lithium diisopropyl amide 作用下， 生成 2-hydroxy-hexa-2,4-dienoic acid
  参考文献：
  名称：

  α-羟基乙酸烯丙基酯和α-苯硫基乙酸酯的酯烯酸酯克莱森重排

  摘要：

  烯丙基α-羟基乙酸酯和α-苯硫基乙酸酯的酯烯酸酯经历克莱森重排，得到α-取代的-γ，δ-不饱和酸。

  DOI：

  10.1016/s0040-4039(00)87631-5

文献信息

• Nontargeted Profiling of Coenzyme A thioesters in biological samples by tandem mass spectrometry
  作者：Michael Zimmermann、Verena Thormann、Uwe Sauer、Nicola Zamboni

  DOI：10.1021/ac401555n

  日期：2013.9.3

  Coenzyme A (CoA) thioesters are ubiquitously present in metabolic networks and play a pivotal role in enzymatic formation and cleavage of carbon–carbon bonds. We present a method allowing nontargeted profiling of CoA-thioesters in biological samples. The reported UHPLC-MS/MS approach employes ion-pairing chromatography to separate CoA-metabolites carrying different chemical functionalities such as hydroxyl or multiple carboxyl groups and to distinguish between isomers. Selective detection of CoA-thioesters is accomplished by precursor ion scanning on a triple quadrupole mass spectrometer and takes advantage of the abundant fragment with m/z = −408 that originates from the CoA-moiety. We used a mixture of 19 commercially available CoA-derivatives to develop and optimize our method. As a proof of concept we demonstrated detection of the major CoA-intermediates of branched chain amino acid degradation in biological samples. We then applied our method to investigate degradation of lipids in the microorganism Mycobacterium smegmatis. Profiling of CoA-thioesters led to the discovery of a novel intermediate of cholesterol degradation. This demonstrates the power of our method for untargeted profiling of CoA-thioesters and adds a missing link in mycobacterial cholesterol catabolism.

  辅酶A（CoA）硫酯广泛存在于代谢网络中，在酶的形成和碳-碳键的断裂中起着关键作用。我们提出了一种对生物样品中的辅酶A硫酯进行非靶向分析的方法。所报道的UHPLC-MS/MS方法采用离子对色谱法分离具有不同化学功能（如羟基或多个羧基）的辅酶A代谢物，并区分异构体。通过三重四极杆质谱仪上的母离子扫描，利用辅酶A部分产生的m/z = −408的丰富碎片，实现对辅酶A硫酯的选择性检测。我们使用19种市售辅酶A衍生物的混合物来开发和优化我们的方法。作为概念验证，我们证明了在生物样品中检测支链氨基酸降解的主要辅酶A中间体。然后，我们将这种方法应用于研究微生物Mycobacterium smegmatis中脂质的降解。通过对辅酶A硫酯的分析，我们发现了胆固醇降解的一种新型中间体。这证明了我们的方法在辅酶A硫酯的非靶向分析方面的强大功能，并填补了分枝杆菌胆固醇分解代谢中缺失的一环。
• The ester enolate claisen rearrangement of allyl α-hydroxyacetates and α-phenylthioacetates
  作者：David J. Ager、Richard C. Cookson

  DOI：10.1016/s0040-4039(00)87631-5

  日期：1982.1

  The ester enolates of allylα-hydroxyacetates and α-phenylthioacetates undergo a Claisen rearrangement to give α-substituted-γ,δ-unsaturated acids.

  烯丙基α-羟基乙酸酯和α-苯硫基乙酸酯的酯烯酸酯经历克莱森重排，得到α-取代的-γ，δ-不饱和酸。