2,6-dimethylheptanoyl-CoA | 204120-64-9

• 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: 2,6-dimethylheptanoyl-CoA
• 英文别名: 2,6-Dimethylheptanoyl-CoA；S-[2-[3-[[(2R)-4-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3,3-dimethylbutanoyl]amino]propanoylamino]ethyl] 2,6-dimethylheptanethioate
• CAS: 204120-64-9
• 化学式: C₃₀H₅₂N₇O₁₇P₃S
• 分子量: 907.767
• InChiKey: GPXWBKWDXPBLKS-LNSOOWQSSA-N

物化性质

• 熔点：
  >183°C (dec.)
• 密度：
  1.69±0.1 g/cm3(Predicted)
• 溶解度：
  可微溶于水

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  58
• 可旋转键数：
  25
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  389
• 氢给体数：
  9
• 氢受体数：
  22

反应信息

• 作为产物：
  描述：

  6-甲基-2-庚醇 在 吡啶 、 乙醇 、 硫酸 、 potassium hydrogencarbonate 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 48.17h， 生成 2,6-dimethylheptanoyl-CoA
  参考文献：
  名称：

  Synthesis and characterization of cis-4-decenoyl-CoA, 3-phenylpropionyl-CoA, and 2,6-dimethylheptanoyl-CoA

  摘要：

  The measurement of acyl-CoA dehydrogenase activities is an essential part of the investigation of patients with suspected defects in fatty acid oxidation. Multiple methods are available for the synthesis of the substrates used for measuring acyl-CoA dehydrogenase activities: however, the yields are low and the products are used without purification. In addition, the reported characterization of acyl-CoAs focuses on the CoA moiety, not on the acyl group. Here we describe the synthesis of three medium-chain acyl-CoAs from mixed anhydrides of the fatty acids using an aqueous-organic solvent mixture optimized to obtain the highest yield. First, cis-4-decenoic acid and 2,6-dimethylheptanoic acid were prepared (3-phenylpropionic acid is commercially available). These were characterized by gas chromatography/mass spectrometry (GC/MS), H-1 nuclear magnetic resonance (NMR), and C-13 NMR. Then cis-4-decenoyl-CoA, 3-phenylpropionyl-CoA, and 2,6-dimethylheptanoyl-CoA were synthesized. These were then purified by ion exchange solid-phase extraction using 2-(2-pyridyl)ethyl-functionalized silica gel, followed by reversed-phase semipreparative high-performance liquid chromatography with ultraviolet detection (HPLC-UV). The purified acyl-CoAs were characterized by analytical HPLC-UV followed by data-dependent tandem mass spectrometry (MS/MS) analysis on the largest responding MS mass (HPLC-UV-MS-MS/MS) and 13C NMR. The yields of the purified acyl-CoAs were between 75% and 78% based on coenzyme A trilithium salt (CoASH). Acyl-CoA dehydrogenase activities were measured in rat skeletal muscle mitochondria using, as substrates, the synthesized cis-4-decenoyl-CoA, 3-phenylpropionyl-CoA, and 2,6-dimethylheptanoyl-CoA. These results were compared with the results using our standard substrates butyryl-CoA, octanoyl-CoA, and palmitoyl-CoA. (C) 2010 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.ab.2010.02.026

文献信息

• TREATMENT OF MEDIUM-CHAIN ACYL-COA DEHYDROGENASE DEFICIENCY
  申请人：University of Pittsburgh - Of the Commonwealth System of Higher Education

  公开号：EP2838522A1

  公开（公告）日：2015-02-25
• Treatment of Medium-Chain Acyl-CoA Dehydrogenase Deficiency
  申请人：University of Pittsburgh - of the Commonwealth System of Higher Education

  公开号：US20150216824A1

  公开（公告）日：2015-08-06

  The present invention provides for methods and compositions for treating medium chain acyl-CoA dehydrogenase deficiency. It is based, at least in part, on the discovery that phenylbutyrate can serve as a substrate for medium chain acyl-CoA dehydrogenase. In non-limiting embodiments, phenylbutyrate and/or another source of phenylacetate is administered as a chaperone treatment to patients suffering from medium chain acyl-CoA dehydrogenase deficiency.
• TREATMENT OF MEDIUM-CHAIN ACYL-CoA DEHYDROGENASE DEFICIENCY
  申请人：UNIVERSITY OF PITTSBURGH - OF THE COMMONWEALTH SYSTEM OF HIGHER EDUCATION

  公开号：US20160166522A1

  公开（公告）日：2016-06-16

  The present invention provides for methods and compositions for treating medium chain acyl-CoA dehydrogenase deficiency. It is based, at least in part, on the discovery that phenylbutyrate can serve as a substrate for medium chain acyl-CoA dehydrogenase. In non-limiting embodiments, phenylbutyrate and/or another source of phenylacetate is administered as a chaperone treatment to patients suffering from medium chain acyl-CoA dehydrogenase deficiency.
• Method of Treating Fatty Acid Oxidation Disorders Using Omega3/Omega6 Unsaturated or Branched Chain Fatty Acids
  申请人：Univeersity of Pittsburgh - Of the Commonwealth System of Higher Eduction

  公开号：US20210322357A1

  公开（公告）日：2021-10-21

  A method of treating medium chain acyl-CoA dehydrogenase deficiency, very long chain acyl-CoA dehydrogenase deficiency, long chain hydroxyacyl-CoA dehydrogenase deficiency, trifunctional protein deficiency, or CPT II deficiency in a patient is provided comprising administering to the patient a therapeutic amount of a triglyceride or other conjugated fatty acid, that bypasses or leads to an intermediate that bypasses the deficient enzyme. Amino acid-conjugated fatty acids also are provided as well as compositions comprising the amino acid-conjugated fatty acids.
• US9283200B2
  申请人：——

  公开号：US9283200B2

  公开（公告）日：2016-03-15