(8R)-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-(3R)-hydroxynonanoic acid | 1355682-49-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (8R)-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-(3R)-hydroxynonanoic acid
• 英文别名: (3R,8R)-8-[(3,6-dideoxy-alpha-L-arabino-hexopyranosyl)oxy]-3-hydroxynonanoic acid；(3R,8R)-8-[(2R,3R,5R,6S)-3,5-dihydroxy-6-methyloxan-2-yl]oxy-3-hydroxynonanoic acid
• CAS: 1355682-49-3
• 化学式: C₁₅H₂₈O₇
• 分子量: 320.383
• InChiKey: WNUSOZJRAZSLBP-AOWZIMASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (R)-ethyl 3-(tert-butyldimethylsilyloxy)hex-5-enoate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 三氟甲磺酸三甲基硅酯 、 palladium 10% on activated carbon 、 水 、 氢气 、 对苯醌 、 lithium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 二氯甲烷 为溶剂， 反应 68.5h， 生成 (8R)-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-(3R)-hydroxynonanoic acid
  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

文献信息

• [EN] SMALL MOLECULE COMPOUNDS FOR THE CONTROL OF NEMATODES<br/>[FR] COMPOSÉS À PETITE MOLÉCULES POUR LA LUTTE CONTRE LES NÉMATODES
  申请人：THOMPSON BOYCE PLANT RES

  公开号：WO2013022985A3

  公开（公告）日：2013-07-25
• Comparative Metabolomics Reveals Biogenesis of Ascarosides, a Modular Library of Small-Molecule Signals in <i>C. elegans</i>
  作者：Stephan H. von Reuss、Neelanjan Bose、Jagan Srinivasan、Joshua J. Yim、Joshua C. Judkins、Paul W. Sternberg、Frank C. Schroeder

  DOI：10.1021/ja210202y

  日期：2012.1.25

  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.