5-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)pentanoic acid | 1355681-20-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)pentanoic acid
• 英文别名: 5-(((2R,3R,5R,6S)-3,5-dihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)pentanoic acid；5-[(3,6-dideoxy-alpha-L-arabino-hexopyranosyl)oxy]pentanoic acid；5-[(2R,3R,5R,6S)-3,5-dihydroxy-6-methyloxan-2-yl]oxypentanoic acid
• CAS: 1355681-20-7
• 化学式: C₁₁H₂₀O₆
• 分子量: 248.276
• InChiKey: RGLRYSHQCRBEIV-YSSBGUOXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 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：

  5-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)pentanoic acid 在 盐酸 、 4-二甲氨基吡啶 、 ethylene dichloride hydrochloride 、 palladium 10% on activated carbon 、 氢气 、 sodium hydride 、 lithium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 mineral oil 为溶剂， 反应 16.12h， 生成 (R)-4-(((2R,3R,5R,6S)-3-((5-(((2R,3R,5R,6S)-3,5-dihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)pentanoyl)oxy)-6-methyl-5-(((R)-2-methyl-3-ureidopropanoyl)oxy)tetrahydro-2H-pyran-2-yl)oxy)pentanoic acid
  参考文献：
  名称：

  复杂的小分子结构调节线虫的表型可塑性

  摘要：

  蠕虫的化学方法：线虫Pristionchus pacificus从初级代谢的修饰构建块构建精细的小分子，包括一种不寻常的基于吡喃木糖的核苷（见方案）。这些化合物作为信号分子来控制成体表型可塑性和多尔发育，并提供后生动物结构多样性模块化生成的例子。

  DOI：

  10.1002/anie.201206797
• 作为产物：
  描述：

  5-(3'R,5'R-dibenzoyloxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)pentanoic acid methyl ester 在 lithium hydroxide 、 叔丁醇 作用下， 以23%的产率得到5-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)pentanoic acid
  参考文献：
  名称：

  秀丽隐杆线虫中的蛔苷活性高度依赖于化学结构

  摘要：

  线虫秀丽隐杆线虫分泌蛔苷，3,6-双脱氧糖蛔糖的结构多样的衍生物，并将它们用于化学通讯。在高人口密度下，特定的蛔苷（统称为 dauer 信息素）会触发进入抗应激的 dauer 幼虫阶段。为了研究蛔苷的构效关系，我们合成了一组蛔苷并测试它们的诱导活性。该面板包括许多在粗信息素提取物中检测到但尚未指定功能的天然蛔苷，以及许多非天然蛔苷衍生物。大多数这些蛔苷（其中一些与天然 dauer 信息素成分具有显着的结构相似性）几乎没有诱导 dauer 的活性。

  DOI：

  10.1016/j.bmc.2013.07.018

文献信息

• 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.
• [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
• Complex Small-Molecule Architectures Regulate Phenotypic Plasticity in a Nematode
  作者：Neelanjan Bose、Akira Ogawa、Stephan H. von Reuss、Joshua J. Yim、Erik J. Ragsdale、Ralf J. Sommer、Frank C. Schroeder

  DOI：10.1002/anie.201206797

  日期：2012.12.7

  Chemistry the worm's way: The nematode Pristionchus pacificus constructs elaborate small molecules from modified building blocks of primary metabolism, including an unusual xylopyranose‐based nucleoside (see scheme). These compounds act as signaling molecules to control adult phenotypic plasticity and dauer development and provide examples of modular generation of structural diversity in metazoans

  蠕虫的化学方法：线虫Pristionchus pacificus从初级代谢的修饰构建块构建精细的小分子，包括一种不寻常的基于吡喃木糖的核苷（见方案）。这些化合物作为信号分子来控制成体表型可塑性和多尔发育，并提供后生动物结构多样性模块化生成的例子。
• Ascaroside activity in Caenorhabditis elegans is highly dependent on chemical structure
  作者：Kyle A. Hollister、Elizabeth S. Conner、Xinxing Zhang、Mark Spell、Gary M. Bernard、Pratik Patel、Ana Carolina G.V. de Carvalho、Rebecca A. Butcher、Justin R. Ragains

  DOI：10.1016/j.bmc.2013.07.018

  日期：2013.9

  panel of ascarosides and tested them for dauer-inducing activity. This panel includes a number of natural ascarosides that were detected in crude pheromone extract, but as yet have no assigned function, as well as many unnatural ascaroside derivatives. Most of these ascarosides, some of which have significant structural similarity to the natural dauer pheromone components, have very little dauer-inducing

  线虫秀丽隐杆线虫分泌蛔苷，3,6-双脱氧糖蛔糖的结构多样的衍生物，并将它们用于化学通讯。在高人口密度下，特定的蛔苷（统称为 dauer 信息素）会触发进入抗应激的 dauer 幼虫阶段。为了研究蛔苷的构效关系，我们合成了一组蛔苷并测试它们的诱导活性。该面板包括许多在粗信息素提取物中检测到但尚未指定功能的天然蛔苷，以及许多非天然蛔苷衍生物。大多数这些蛔苷（其中一些与天然 dauer 信息素成分具有显着的结构相似性）几乎没有诱导 dauer 的活性。