| 1355683-83-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• CAS: 1355683-83-8
• 化学式: C₂₄H₃₈O₅Si
• 分子量: 434.648
• InChiKey: QLLFYNPSZUYKCS-TZIWHRDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.91
• 重原子数：
  30.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  在 三氟甲磺酸三甲基硅酯 、 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 43.5h， 生成 ethyl (8R)-(3'R,5'R-dibenzyloxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-(3R)-hydroxynonanoate
  参考文献：
  名称：

  Comparative Metabolomics Reveals Biogenesis of Ascarosides, a Modular Library of Small-Molecule Signals in C. elegans

  摘要：

  In the model organism Caenorhabditis elegans, a family of endogenous small molecules, the ascarosides function as key regulators of developmental timing and behavior that act upstream of conserved signaling pathways. The ascarosides are based on the dideoxysugar ascarylose, which is linked to fatty-acid-like side chains of varying lengths derived from peroxisomal beta-oxidation. Despite the importance of ascarosides for many aspects of C. elegans biology, knowledge of their structures, biosynthesis, and homeostasis remains incomplete. We used an MS/MS-based screen to profile ascarosides in C. elegans wild-type and mutant metabolomes, which revealed a much greater structural diversity of ascaroside derivatives than previously reported. Comparison of the metabolomes from wildtype and a series of peroxisomal beta-oxidation mutants showed that the enoyl CoA-hydratase MAOC-1 serves an important role in ascaroside biosynthesis and clarified the functions of two other enzymes, ACOX-1 and DHS-28. We show that, following peroxisomal beta-oxidation, the ascarosides are selectively derivatized with moieties of varied biogenetic origin and that such modifications can dramatically affect biological activity, producing signaling molecules active at low femtomolar concentrations. Based on these results, the ascarosides appear as a modular library of small-molecule signals, integrating building blocks from three major metabolic pathways: carbohydrate metabolism, peroxisomal beta-oxidation of fatty acids, and amino acid catabolism. Our screen further demonstrates that ascaroside biosynthesis is directly affected by nutritional status and that excretion of the final products is highly selective.

  DOI：

  10.1021/ja210202y
• 作为产物：
  描述：

  [(2R)-pent-4-en-2-yl] benzoate 、 (R)-ethyl 3-(tert-butyldimethylsilyloxy)hex-5-enoate 在 对苯醌 、 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 20.17h， 生成
  参考文献：
  名称：

  [EN] SMALL MOLECULE COMPOUNDS FOR THE CONTROL OF NEMATODES
  [FR] COMPOSÉS À PETITE MOLÉCULES POUR LA LUTTE CONTRE LES NÉMATODES

  摘要：

  公开号：

  WO2013022985A3