benzyl 4-oxo-5-hexenoate | 1442081-35-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl 4-oxo-5-hexenoate
• 英文别名: Benzyl 4-oxohex-5-enoate
• CAS: 1442081-35-7
• 化学式: C₁₃H₁₄O₃
• 分子量: 218.252
• InChiKey: LDANUUQKWFXUIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzyl 4-oxo-5-hexenoate 在 双氧水 、 potassium carbonate 作用下， 以 水 、 叔丁醇 为溶剂， 反应 3.0h， 以98%的产率得到benzyl 4-oxo-5,6-epoxyhexanoate
  参考文献：
  名称：

  Bioavailable affinity label for collagen prolyl 4-hydroxylase

  摘要：

  Collagen is the most abundant protein in animals. Its prevalent 4-hydroxyproline residues contribute greatly to its conformational stability. The hydroxyl groups arise from a post-translational modification catalyzed by the nonheme iron-dependent enzyme, collagen prolyl 4-hydroxylase (P4H). Here, we report that 4-oxo-5,6-epoxyhexanoate, a mimic of the alpha-ketoglutarate co-substrate, inactivates human P4H. The inactivation installs a ketone functionality in P4H, providing a handle for proteomic experiments. Caenorhabditis elegans exposed to the esterified epoxy ketone displays the phenotype of a worm lacking P4H. Thus, this affinity label can be used to mediate collagen stability in an animal, as is desirable in the treatment of a variety of fibrotic diseases. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.04.057
• 作为产物：
  描述：

  琥珀酸苄酯 在 trans-benzyl(chloro)-bis(triphenylphosphine)palladium(II) 作用下， 以 六甲基磷酰三胺 、 二氯甲烷 为溶剂， 反应 0.66h， 生成 benzyl 4-oxo-5-hexenoate
  参考文献：
  名称：

  Bioavailable affinity label for collagen prolyl 4-hydroxylase

  摘要：

  Collagen is the most abundant protein in animals. Its prevalent 4-hydroxyproline residues contribute greatly to its conformational stability. The hydroxyl groups arise from a post-translational modification catalyzed by the nonheme iron-dependent enzyme, collagen prolyl 4-hydroxylase (P4H). Here, we report that 4-oxo-5,6-epoxyhexanoate, a mimic of the alpha-ketoglutarate co-substrate, inactivates human P4H. The inactivation installs a ketone functionality in P4H, providing a handle for proteomic experiments. Caenorhabditis elegans exposed to the esterified epoxy ketone displays the phenotype of a worm lacking P4H. Thus, this affinity label can be used to mediate collagen stability in an animal, as is desirable in the treatment of a variety of fibrotic diseases. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.04.057

文献信息

• Bioavailable affinity label for collagen prolyl 4-hydroxylase
  作者：James D. Vasta、Joshua J. Higgin、Elizabeth A. Kersteen、Ronald T. Raines

  DOI：10.1016/j.bmc.2013.04.057

  日期：2013.6

  Collagen is the most abundant protein in animals. Its prevalent 4-hydroxyproline residues contribute greatly to its conformational stability. The hydroxyl groups arise from a post-translational modification catalyzed by the nonheme iron-dependent enzyme, collagen prolyl 4-hydroxylase (P4H). Here, we report that 4-oxo-5,6-epoxyhexanoate, a mimic of the alpha-ketoglutarate co-substrate, inactivates human P4H. The inactivation installs a ketone functionality in P4H, providing a handle for proteomic experiments. Caenorhabditis elegans exposed to the esterified epoxy ketone displays the phenotype of a worm lacking P4H. Thus, this affinity label can be used to mediate collagen stability in an animal, as is desirable in the treatment of a variety of fibrotic diseases. (C) 2013 Elsevier Ltd. All rights reserved.