(E)-4-hydroxy-3-methyl-2-butenyl β-D-glucopyranoside

• 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: (E)-4-hydroxy-3-methyl-2-butenyl β-D-glucopyranoside
• 英文别名: (e)-2-methyl-2-butene-1,4-diol 4-O-beta-d-glucopyranoside；(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(E)-4-hydroxy-3-methylbut-2-enoxy]oxane-3,4,5-triol
• 化学式: C₁₁H₂₀O₇
• 分子量: 264.276
• InChiKey: MTNPSFBFGZMJPZ-ZCIPGPJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  120
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (E)-4-hydroxy-3-methyl-2-butenyl β-D-glucopyranoside 在 almond β-glucosidase 作用下， 以 acetate buffer 为溶剂， 反应 4.0h， 以7.1 mg的产率得到2-methyl but-2-ene-1,4-diol
  参考文献：
  名称：

  一种半萜糖苷作为豆蚜的探测威慑物，Megoura crassicauda，来自非寄主野豌豆，Vicia hirsuta

  摘要：

  豆蚜 Megoura crassicauda Mordvilko 选择性地取食属于豌豆属（豆科）的植物。然而，它从不侵扰微小的野豌豆，V. hirsuta (L.) Gray。蚜虫似乎通过在其管心针穿透植物组织的过程中品尝特定的化学物质来区分寄主和非寄主植物。蚜虫在受到特定探测刺激物的刺激后，通过一层石蜡膜沉积特征性的蛋白质管心针鞘，该膜的一侧与 Vicia angustifolia 的提取物溶液接触。然而，向培养基中添加多毛蕨提取物会强烈抑制唾液鞘的形成。通过监测抑制作用从 V. hirsuta 提取物中分离出一种特定的探测威慑物，并鉴定为 (E)-2-methyl-2-butene-1,4-diol 4-O-beta-d-glucopyranoside。在植物中发现的糖苷和刺激性 V. angustifolia 部分的混合物显着降低了 M. crassicauda 的探测活性。由于管心

  DOI：

  10.1016/j.phytochem.2005.12.013
• 作为产物：
  描述：

  在 ammonium hydroxide 作用下， 反应 8.0h， 生成 (E)-4-hydroxy-3-methyl-2-butenyl β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and immunological evaluation of the 4-β-glucoside of HMBPP

  摘要：

  HMBPP ((E)-4-hydroxy-3-methyl-2-butenyl pyrophosphate) is a highly potent innate immunogen that stimulates human gamma delta T cells expressing the V gamma 2V delta 2 T cell antigen receptor. To determine if glycoside conjugates of HMBPP retain activity, the 4-beta-glucoside and its acetylated homolog were synthesized and tested for their ability to stimulate gamma delta T cells. The glycoside HMBPP conjugate stimulated human gamma delta T cells with an EC50 of 78 nM. The tetraacetyl glycoside HMBPP conjugate was also active (EC50 = 360 nM). The two isomeric mono-beta-glucosides of the parent (E)-2-methylbut-2-ene-1,4-diol, however, were not active. Thus, HMBPP glycosylated at the 4-OH position stimulates gamma delta T cells as long as the pyrophosphate moiety is present. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.055

文献信息

• A hemiterpene glucoside as a probing deterrent of the bean aphid, Megoura crassicauda, from a non-host vetch, Vicia hirsuta
  作者：Naohiro Ohta、Naoki Mori、Yasumasa Kuwahara、Ritsuo Nishida

  DOI：10.1016/j.phytochem.2005.12.013

  日期：2006.3

  with an extract solution of Vicia angustifolia. However, an addition of a V. hirsuta extract to the medium strongly inhibited the salivary sheath formation. A specific probing deterrent was isolated from a V. hirsuta extract by monitoring the inhibitory effect, and identified as (E)-2-methyl-2-butene-1,4-diol 4-O-beta-d-glucopyranoside. A mixture of the glycoside and the stimulatory V. angustifolia

  豆蚜 Megoura crassicauda Mordvilko 选择性地取食属于豌豆属（豆科）的植物。然而，它从不侵扰微小的野豌豆，V. hirsuta (L.) Gray。蚜虫似乎通过在其管心针穿透植物组织的过程中品尝特定的化学物质来区分寄主和非寄主植物。蚜虫在受到特定探测刺激物的刺激后，通过一层石蜡膜沉积特征性的蛋白质管心针鞘，该膜的一侧与 Vicia angustifolia 的提取物溶液接触。然而，向培养基中添加多毛蕨提取物会强烈抑制唾液鞘的形成。通过监测抑制作用从 V. hirsuta 提取物中分离出一种特定的探测威慑物，并鉴定为 (E)-2-methyl-2-butene-1,4-diol 4-O-beta-d-glucopyranoside。在植物中发现的糖苷和刺激性 V. angustifolia 部分的混合物显着降低了 M. crassicauda 的探测活性。由于管心
• Synthesis and immunological evaluation of the 4-β-glucoside of HMBPP
  作者：José-Luis Giner、Hong Wang、Craig T. Morita

  DOI：10.1016/j.bmcl.2011.12.055

  日期：2012.1

  HMBPP ((E)-4-hydroxy-3-methyl-2-butenyl pyrophosphate) is a highly potent innate immunogen that stimulates human gamma delta T cells expressing the V gamma 2V delta 2 T cell antigen receptor. To determine if glycoside conjugates of HMBPP retain activity, the 4-beta-glucoside and its acetylated homolog were synthesized and tested for their ability to stimulate gamma delta T cells. The glycoside HMBPP conjugate stimulated human gamma delta T cells with an EC50 of 78 nM. The tetraacetyl glycoside HMBPP conjugate was also active (EC50 = 360 nM). The two isomeric mono-beta-glucosides of the parent (E)-2-methylbut-2-ene-1,4-diol, however, were not active. Thus, HMBPP glycosylated at the 4-OH position stimulates gamma delta T cells as long as the pyrophosphate moiety is present. (C) 2011 Elsevier Ltd. All rights reserved.