chlorofumaric acid | 617-42-5

• 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: chlorofumaric acid
• 英文别名: Chlorfumarsaeure；2-chlorofumaric acid；(Z)-2-chlorobut-2-enedioic acid
• CAS: 617-42-5
• 化学式: C₄H₃ClO₄
• 分子量: 150.518
• InChiKey: ZQHJVIHCDHJVII-UPHRSURJSA-N

物化性质

• 熔点：
  191-192 °C
• 沸点：
  326.0±27.0 °C(Predicted)
• 密度：
  1.698±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  chlorofumaric acid 生成 2-chloromaleic acid
  参考文献：
  名称：

  Perkin, Journal of the Chemical Society, 1888, vol. 53, p. 703

  摘要：

  DOI：
• 作为产物：
  描述：

  2-chloromaleic acid 在 盐酸 作用下， 生成 chlorofumaric acid
  参考文献：
  名称：

  Perkin, Journal of the Chemical Society, 1888, vol. 53, p. 703

  摘要：

  DOI：

文献信息

• Enantiospecific synthesis of 3-substituted aspartic acids via enzymic amination of substituted fumaric acids
  作者：Mahmoud Akhtar、Botting Nigel P.、Cohen Mark A.、David Gani

  DOI：10.1016/s0040-4020(01)87795-4

  日期：——

  The use of the enzyme 3-methylaspartase in the synthesis of L-aspartic acids containing 3-halogeno- or 3-alkyl- substituents, in the (S)-configuration, and also some of the corresponding C-3 deuteriated isotopomers is described.

  描述了3-甲基天冬氨酸酶在合成具有（S）构型的3-卤代-或3-烷基-取代基的L-天冬氨酸以及一些相应的C-3氘代异位异构体中的用途。
• Enzymic synthesis of 3-halogenoaspartic acids using β-methylaspartase: inhibition by 3-bromoaspartic acid
  作者：Mahmoud Akhtar、Mark A. Cohen、David Gani

  DOI：10.1039/c39860001290

  日期：——

  In the presence of ammonia, β-methylaspartase catalyses the conversion of halogenofumaric acids into the corresponding β-halogenoaspartic acids; one of the products, bromoaspartic acid, is an irreversible inhibitor.

  在氨存在下，β-甲基天冬氨酸酶催化卤代富马酸转化为相应的β-卤代氨基天冬氨酸；产品之一是溴天冬氨酸，是不可逆的抑制剂。
• Purification and Properties of Crystalline 3-Methylaspartase from Two Facultative Anaerobes,<i>Citrobacter</i>sp. Strain YG-0504 and<i>Morganella morganii</i>Strain YG-0601
  作者：Yasuo Kato、Yasuhisa Asano

  DOI：10.1271/bbb.59.93

  日期：1995.1

  3-Methylaspartase (3-methylaspartate ammonia-lyase, EC 4.3.1.2) from two facultative anaerobes from soil, Citrobacter sp. strain YG-0504 and Morganella morganii strain YG-0601, were purified and crystallized from their crude extracts. Both of the Citrobacter and Morganella enzymes appeared to be a dimer of subunits of Mr 40,000 and 44,000, respectively. The enzymes had similar enzymological properties: optimum pH for the deamination reaction of (2S, 3S)-3-methylaspartic acid, substrate specificity, inhibitor, divalent and monovalent cation requirement, and N-terminal amino acid sequence homology. However, some differences were detected in pH and temperature stability, optimum pH for the amination reaction of mesaconic acid, optimum temperature, specific activity, and stability during electrophoresis. Both enzymes had similar enzymological properties to the known 3-methylaspartase from an obligate anaerobic bacterium, Clostridium tetanomorphum H1, except kinetic constants and substrate specificities.

  从土壤中的两种兼性厌氧菌--柠檬酸杆菌菌株 YG-0504 和摩根氏菌菌株 YG-0601 的粗提取物中纯化并结晶出了 3-甲基天冬氨酸氨水解酶（3-甲基天冬氨酸氨水解酶，EC 4.3.1.2）。柠檬酸杆菌和摩根氏菌的酶似乎都是二聚体，其亚基的摩尔数分别为 40,000 和 44,000。这两种酶具有相似的酶学特性：(2S, 3S)-3-甲基天冬氨酸脱氨反应的最适 pH 值、底物特异性、抑制剂、二价和一价阳离子要求以及 N 端氨基酸序列同源性。然而，在 pH 值和温度稳定性、中酸胺化反应的最适 pH 值、最适温度、特异活性和电泳稳定性方面发现了一些差异。除了动力学常数和底物特异性外，这两种酶的酶学特性与已知的3-甲基天冬氨酸酶（来自一种必须厌氧细菌--四价梭菌H1）相似。
• Antifungal Properties of Halofumarate Esters
  作者：Herman Gershon、Larry Shanks

  DOI：10.1002/jps.2600670443

  日期：1978.4

  mucedo, methyl fluorofumarate (0.037 mmole/liter); and T. mentagrophytes, ethyl iodofumarate (0.020 mmole/liter). The order of overall activity of the six most toxic compounds was: ethyl iodofumarate greater than ethyl chlorofumarate greater than methyl iodofumarate = methyl bromofumarate greater than methyl chlorofumarate greater than bromofumarate.

  在Sabouraud葡萄糖琼脂琼脂培养基中不存在和存在10％牛肉血清的情况下，在pH值为5.6和7.0的情况下，测试了四种卤代富马酸的烷基酯（C1-C4）对白色念珠菌，黑曲霉，Mucor mucedo和毛癣菌的抗真菌活性。 。对每种生物毒性最大的化合物是：白色念珠菌，碘富马酸乙酯（0.054 mmole /升）；黑曲霉，溴代富马酸甲酯（0.090 mmole /升）；Mucedo Mucedo，富马酸氟甲酯（0.037 mmol / L）；和T. mentagrophytes，碘富马酸乙酯（0.020 mmole /升）。六个毒性最高的化合物的总体活性顺序为：碘富马酸乙酯大于氯富马酸乙酯大于碘富马酸甲酯=溴代富马酸甲酯大于氯代富马酸甲酯大于溴代富马酸甲酯。
• Stereochemical course of the enzymic amination of chloro- and bromo- fumaric acid by 3-methylaspartate ammonia-lyase
  作者：Mahmoud Akhtar、Mark A Cohen、David Gani

  DOI：10.1016/s0040-4039(00)96139-2

  日期：——

  Enzymic amination of chloro- and bromo- fumaric acid using 3-methylaspartate ammonia-lyase in the presence of ammonia leads to the formation of 3-chloro- and 3-bromo-aspartic acid respectively; the absolute configuration of each product is (R) at C-2 and (S) at C-3.

  在氨存在下，使用3-甲基天冬氨酸氨裂合酶对氯-和富马酸进行酶促胺化反应分别导致3-氯-和3-溴-天冬氨酸的形成。每个产品的绝对构型在C-2为（R），在C-3为（S）。