(R,E)-8-(((2R,3R,5R,6S)-3-hydroxy-6-methyl-5-(((E)-2-methylbut-2-enoyl)oxy)tetrahydro-2H-pyran-2-yl)oxy)non-2-enoic acid | 1355681-26-3

• 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: (R,E)-8-(((2R,3R,5R,6S)-3-hydroxy-6-methyl-5-(((E)-2-methylbut-2-enoyl)oxy)tetrahydro-2H-pyran-2-yl)oxy)non-2-enoic acid
• 英文别名: (2E,8R)-8-({3,6-dideoxy-4-O-[(2E)-2-methylbut-2-enoyl]-alpha-L-arabino-hexopyranosyl}oxy)non-2-enoic acid；(E,8R)-8-[(2R,3R,5R,6S)-3-hydroxy-6-methyl-5-[(E)-2-methylbut-2-enoyl]oxyoxan-2-yl]oxynon-2-enoic acid
• CAS: 1355681-26-3
• 化学式: C₂₀H₃₂O₇
• 分子量: 384.47
• InChiKey: NKVDNSIHZYHTDR-KADWPSLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (E)-2-甲基-2-丁烯酰氯 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 水 、 N,N-二异丙基乙胺 、 lithium hydroxide 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.33h， 生成 (R,E)-8-(((2R,3R,5R,6S)-3-hydroxy-6-methyl-5-(((E)-2-methylbut-2-enoyl)oxy)tetrahydro-2H-pyran-2-yl)oxy)non-2-enoic acid
  参考文献：
  名称：

  线虫信息素a虫苷的模块化和可扩展合成：引发植物防御反应的含义。

  摘要：

  已开发出一种高效，模块化的线虫信息素a虫苷合成方法，该方法突出了通过使用原酸酯化/苄基化/原酸酯重排作为关键步骤，可从市售L-鼠李糖以23％的产率对普通中间体10进行4步可扩展合成的过程。相应地合成了六种不同的scar螨。值得注意的是，生物学研究表明，ascr＃1和ascr＃18处理导致拟南芥叶片中愈伤组织的积累增加。ascr＃18还增加了与防御相关的基因（如PR1，PDF1.2，LOX2和AOS）的表达，这可能有助于增强植物的防御反应。这项研究不仅允许轻松访问1- O，2- O，4- O取代的scar虫甙，还提供了有关其在诱导植物防御反应中的生物学活性及其作用方式的宝贵见解。

  DOI：

  10.1039/d0ob00652a

文献信息

• Improved Synthesis for Modular Ascarosides Uncovers Biological Activity
  作者：Ying K. Zhang、Marco A. Sanchez-Ayala、Paul W. Sternberg、Jagan Srinivasan、Frank C. Schroeder

  DOI：10.1021/acs.orglett.7b01009

  日期：2017.6.2

  A versatile synthesis of modular ascarosides, a family of signaling molecules from Caenorhabditis elegans and other nematodes, via hydrogenolysis of a cyclic sulfate derived from methyl-α-l-rhamnopyranoside is reported. The route enables selective introduction of different side chains at the 1, 2, and 4 positions of the sugar, as demonstrated for ascarosides from C. elegans and Pristionchus pacificus

  据报道，通过衍生自甲基-α - 1-鼠李糖吡喃糖苷的环状硫酸盐进行氢解，可以合成一种模块化的scar虫甙，即一种来自秀丽隐杆线虫和其他线虫的信号分子家族。该路线能够在糖的1、2和4位选择性引入不同的侧链，如秀丽隐杆线虫和Pristionchus pacificus的a虫苷所证明的那样。用4'-tigloyl scar虫苷mbas＃3的合成样品进行的生物测定显示出其作为回避或分散信号的作用。
• 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
• Modular and scalable synthesis of nematode pheromone ascarosides: implications in eliciting plant defense response
  作者：Shuai Ning、Lei Zhang、Jinjin Ma、Lan Chen、Guangyao Zeng、Chao Yang、Yingjun Zhou、Xiaoli Guo、Xu Deng

  DOI：10.1039/d0ob00652a

  日期：——

  lation/orthoester rearrangement as the key step. Six diverse ascarosides were synthesized accordingly. Notably, biological investigations revealed that ascr#1 and ascr#18 treatment resulted in enhanced callose accumulation in Arabidopsis leaves. And ascr#18 also increased the expression of defense-related genes such as PR1, PDF1.2, LOX2 and AOS, which might contribute to the enhanced plant defense

  已开发出一种高效，模块化的线虫信息素a虫苷合成方法，该方法突出了通过使用原酸酯化/苄基化/原酸酯重排作为关键步骤，可从市售L-鼠李糖以23％的产率对普通中间体10进行4步可扩展合成的过程。相应地合成了六种不同的scar螨。值得注意的是，生物学研究表明，ascr＃1和ascr＃18处理导致拟南芥叶片中愈伤组织的积累增加。ascr＃18还增加了与防御相关的基因（如PR1，PDF1.2，LOX2和AOS）的表达，这可能有助于增强植物的防御反应。这项研究不仅允许轻松访问1- O，2- O，4- O取代的scar虫甙，还提供了有关其在诱导植物防御反应中的生物学活性及其作用方式的宝贵见解。