(R,E)-9-(((2R,3R,5R,6S)-3,5-dihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)dec-2-enoic acid | 1355681-49-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R,E)-9-(((2R,3R,5R,6S)-3,5-dihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)dec-2-enoic acid
• 英文别名: (2E,9R)-9-[(3,6-dideoxy-alpha-L-arabino-hexopyranosyl)oxy]dec-2-enoic acid；(E,9R)-9-[(2R,3R,5R,6S)-3,5-dihydroxy-6-methyloxan-2-yl]oxydec-2-enoic acid
• CAS: 1355681-49-0
• 化学式: C₁₆H₂₈O₆
• 分子量: 316.395
• InChiKey: MZJGOAYSXTVLMG-NSKGPKHTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  96.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  甲醇 、 (R,E)-9-(((2R,3R,5R,6S)-3,5-dihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)dec-2-enoic acid 、 三甲基硅烷化重氮甲烷 以 乙醚 为溶剂， 反应 1.55h， 以45%的产率得到
  参考文献：
  名称：

  Deep Interrogation of Metabolism Using a Pathway-Targeted Click-Chemistry Approach

  摘要：

  Untargeted metabolomics indicates that the number of unidentified small-molecule metabolites may exceed the number of protein-coding genes for many organisms, including humans, by orders of magnitude. Uncovering the underlying metabolic networks is essential for elucidating the physiological and ecological significance of these biogenic small molecules. Here we develop a click-chemistry-based enrichment strategy, DIMEN (deep interrogation of metabolism via enrichment), that we apply to investigate metabolism of the ascarosides, a family of signaling molecules in the model organism C. elegans. Using a single alkyne modified metabolite and a solid-phase azide resin that installs a diagnostic moiety for MS/MS-based identification, DIMEN uncovered several hundred novel compounds originating from diverse biosynthetic transformations that reveal unexpected intersection with amino acid, carbohydrate, and energy metabolism. Many of the newly discovered transformations could not be identified or detected by conventional LC-MS analyses without enrichment, demonstrating the utility of DIMEN for deeply probing biochemical networks that generate extensive yet uncharacterized structure space.

  DOI：

  10.1021/jacs.0c06877
• 作为产物：
  描述：

  ethyl (R,E)-9-((tert-butyldimethylsilyl)oxy)dec-2-enoate 在 三氟甲磺酸三甲基硅酯 、 氢氟酸 、 水 、 lithium hydroxide 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 乙腈 为溶剂， 反应 22.67h， 生成 (R,E)-9-(((2R,3R,5R,6S)-3,5-dihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)dec-2-enoic acid
  参考文献：
  名称：

  Deep Interrogation of Metabolism Using a Pathway-Targeted Click-Chemistry Approach

  摘要：

  Untargeted metabolomics indicates that the number of unidentified small-molecule metabolites may exceed the number of protein-coding genes for many organisms, including humans, by orders of magnitude. Uncovering the underlying metabolic networks is essential for elucidating the physiological and ecological significance of these biogenic small molecules. Here we develop a click-chemistry-based enrichment strategy, DIMEN (deep interrogation of metabolism via enrichment), that we apply to investigate metabolism of the ascarosides, a family of signaling molecules in the model organism C. elegans. Using a single alkyne modified metabolite and a solid-phase azide resin that installs a diagnostic moiety for MS/MS-based identification, DIMEN uncovered several hundred novel compounds originating from diverse biosynthetic transformations that reveal unexpected intersection with amino acid, carbohydrate, and energy metabolism. Many of the newly discovered transformations could not be identified or detected by conventional LC-MS analyses without enrichment, demonstrating the utility of DIMEN for deeply probing biochemical networks that generate extensive yet uncharacterized structure space.

  DOI：

  10.1021/jacs.0c06877

文献信息

• Deep Interrogation of Metabolism Using a Pathway-Targeted Click-Chemistry Approach
  作者：Jason S. Hoki、Henry H. Le、Karlie E. Mellott、Ying K. Zhang、Bennett W. Fox、Pedro R. Rodrigues、Yan Yu、Maximilian J. Helf、Joshua A. Baccile、Frank C. Schroeder

  DOI：10.1021/jacs.0c06877

  日期：2020.10.28

  Untargeted metabolomics indicates that the number of unidentified small-molecule metabolites may exceed the number of protein-coding genes for many organisms, including humans, by orders of magnitude. Uncovering the underlying metabolic networks is essential for elucidating the physiological and ecological significance of these biogenic small molecules. Here we develop a click-chemistry-based enrichment strategy, DIMEN (deep interrogation of metabolism via enrichment), that we apply to investigate metabolism of the ascarosides, a family of signaling molecules in the model organism C. elegans. Using a single alkyne modified metabolite and a solid-phase azide resin that installs a diagnostic moiety for MS/MS-based identification, DIMEN uncovered several hundred novel compounds originating from diverse biosynthetic transformations that reveal unexpected intersection with amino acid, carbohydrate, and energy metabolism. Many of the newly discovered transformations could not be identified or detected by conventional LC-MS analyses without enrichment, demonstrating the utility of DIMEN for deeply probing biochemical networks that generate extensive yet uncharacterized structure space.