4-nitrobenzyl β-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-nitrobenzyl β-D-glucopyranoside
• 英文别名: (4-Nitrophenyl)methyl-b-D-glucopyranoside；(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(4-nitrophenyl)methoxy]oxane-3,4,5-triol
• 化学式: C₁₃H₁₇NO₈
• 分子量: 315.28
• InChiKey: WDXXNSLGRCTMAE-UJPOAAIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  145
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  可得然胶 、 对硝基苯甲醇 在 Prunus domestica prune seed meal 作用下， 反应 50.0h， 以15%的产率得到4-nitrobenzyl β-D-glucopyranoside
  参考文献：
  名称：

  Using ionic liquid cosolvents to improve enzymatic synthesis of arylalkyl β-d-glucopyranosides

  摘要：

  Enzymatic synthesis of various arylalkyl beta-D-glucopyranosides catalyzed by prune (Prunus domestica) seed meal via reverse hydrolysis in the mixture of organic solvent, ionic liquid (IL) and phosphate buffer was described. Among four hydrophilic organic solvents tested, ethylene glycol diacetate (EGDA) was found to be the most suitable for enzymatic synthesis of salidroside, a bioactive compound of commercial interest, from D-glucose and tyrosol. The effects of the nature of ionic liquids and their contents on the enzymatic glucosylation were studied. The addition of a suitable amount of ILs including denaturing ones was favorable to shift the reaction equilibrium toward the synthesis, thus improving the yields. Among the examined ILs, the novel IL [BMIm]I proved to be the best. And this IL was applied as the solvent in biocatalysis for the first time. The yields were found to be enhanced between 0.2-fold and 0.5-fold after the addition of 10% (v/v) [BMIm]I. In 10% (v/v) [BMIm]I-containing system, the desired arylalkyl beta-D-glucopyranosides were synthesized with 15-28% yields, among which salidroside was obtained with a yield of 22%. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2011.08.009

文献信息

• Use of apple seed meal as a new source of β-glucosidase for enzymatic glucosylation of 4-substituted benzyl alcohols and tyrosol in monophasic aqueous-dioxane medium
  作者：Ai Min Tong、Wen Ya Lu、Jian He Xu、Guo Qiang Lin

  DOI：10.1016/j.bmcl.2004.02.042

  日期：2004.5

  A facile method for enzymatic glycosylation of 4-substituted benzyl alcohols and tyrosol with glucose in a monophasic aqueous-dioxane medium was reported, using a crude meal of apple seed as a new catalyst. The corresponding P-D-glucosides were synthesized in moderate yields (13.1-23.1%), among which the salidroside was obtained in 15.8% yield. (C) 2004 Elsevier Ltd. All rights reserved.