p-nitrophenyl 2,3-di-O-acetyl-α-L-arabinofuranoside | 59997-94-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-nitrophenyl 2,3-di-O-acetyl-α-L-arabinofuranoside
• 英文别名: p-Nitrophenyl-2,3-di-O-acetyl-α-L-arabinofuranosid；[(2S,3S,4R,5S)-4-acetyloxy-2-(hydroxymethyl)-5-(4-nitrophenoxy)oxolan-3-yl] acetate
• CAS: 59997-94-3
• 化学式: C₁₅H₁₇NO₉
• 分子量: 355.301
• InChiKey: YAMPIGNYHMETEF-BYNSBNAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  137
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  p-nitrophenyl 2,3-di-O-acetyl-α-L-arabinofuranoside 在 4-二甲氨基吡啶 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 4-nitrophenyl 5-O-(E)-feruloyl-α-L-arabinofuranoside
  参考文献：
  名称：

  Two efficient ways to 2-O- and 5-O-feruloylated 4-nitrophenyl α-l-arabinofuranosides as substrates for differentiation of feruloyl esterases

  摘要：

  4-Nitrophenyl 2-O-(E)-feruloyl-alpha-L-arabinofuranoside 1 and 4-nitrophenyl 5-O-(E)-feruloyl-alpha-L-arabinofuranoside 2 have been synthesized by two different routes. Monoferuloylation was accomplished by a chemoenzymatic sequence employing a regioselective transesterification catalyzed by lipases. The feruloyl group was introduced to enzymatically prepared 2,3- and 3,5-diacetates of 4-nitrophenyl alpha-L-arabinofurano side by reaction with 4-O-acetylferuloyl chloride. Removal of the protecting acetyl groups yielded 1 and 2. An alternative chemical synthesis suitable for preparation of larger quantities of 1 and 2 also is presented. The new substrates represent convenient tools to differentiate feruloyl esterases on the basis of their substrate specificity. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00038-8
• 作为产物：
  描述：

  p-nitrophenyl 2,3,5-tri-O-acetyl-α-L-arabinofuranoside 在 Lipolyve CC 作用下， 以 phosphate buffer 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以60%的产率得到p-nitrophenyl 2,3-di-O-acetyl-α-L-arabinofuranoside
  参考文献：
  名称：

  Two efficient ways to 2-O- and 5-O-feruloylated 4-nitrophenyl α-l-arabinofuranosides as substrates for differentiation of feruloyl esterases

  摘要：

  4-Nitrophenyl 2-O-(E)-feruloyl-alpha-L-arabinofuranoside 1 and 4-nitrophenyl 5-O-(E)-feruloyl-alpha-L-arabinofuranoside 2 have been synthesized by two different routes. Monoferuloylation was accomplished by a chemoenzymatic sequence employing a regioselective transesterification catalyzed by lipases. The feruloyl group was introduced to enzymatically prepared 2,3- and 3,5-diacetates of 4-nitrophenyl alpha-L-arabinofurano side by reaction with 4-O-acetylferuloyl chloride. Removal of the protecting acetyl groups yielded 1 and 2. An alternative chemical synthesis suitable for preparation of larger quantities of 1 and 2 also is presented. The new substrates represent convenient tools to differentiate feruloyl esterases on the basis of their substrate specificity. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00038-8

文献信息

• Preparation of regioselectively feruloylated p-nitrophenyl α-l-arabinofuranosides and β-d-xylopyranosides—convenient substrates for study of feruloyl esterase specificity
  作者：Mária Mastihubová、Peter Biely

  DOI：10.1016/j.carres.2010.03.034

  日期：2010.6

  as deacetylation method. Under these conditions a significant feruloyl migration was observed mainly on p-nitrophenyl 3-O-feruloyl-beta-D-xylopyranoside resulting in low yields of the positional isomers. Investigation of substrate and positional specificity of different types of feruloyl esterases on the presented compounds in enzyme-coupled assays was reported previously.

  对-硝基苯基α-L-阿拉伯呋喃糖苷和β-D-吡喃吡喃糖苷单-O-阿魏酸酯是通过相应的酶促制备的二-O-乙酸酯的4-O-乙酰基阿魏酸酯化，然后进行脱乙酰化而制备的。在吡喃吡喃糖苷衍生物上测试了由氧化锌催化的另一种轻度酰化反应。使用中性催化剂二丁基氧化锡在回流下对乙酰基进行化学选择性甲醇分解作为脱乙酰基方法。在这些条件下，主要在对硝基苯基3-O-阿魏酰基-β-D-吡喃吡喃糖苷上观察到明显的阿魏酰基迁移，导致位置异构体的产率低。先前已经报道了在酶联测定中研究不同类型的阿魏酸酯酶对所提供化合物的底物和位置特异性的研究。
• The acetates of p-nitrophenyl α-l-arabinofuranoside—Regioselective preparation by action of lipases
  作者：Mária Mastihubová、Jana Szemesová、Peter Biely

  DOI：10.1016/j.bmc.2005.10.023

  日期：2006.3

  mono-O-acetates of p-nitrophenyl alpha-L-arabinofuranoside were prepared by chemoenzymatic way using lipases. The 2,3-di-O-acetate was obtained in 90% yield by deacetylation of the primary acetyl group of per-O-acetylated p-nitrophenyl alpha-L-arabinofuranoside by Candida cylindracea lipase (CCL) or Candida rugosa lipase (LAY). The 2,5- and 3,5-di-O-acetates were obtained by acetylation of p-nitrophenyl alpha-L-arabinofuranoside

  对-硝基苯基α-L-阿拉伯呋喃糖苷的所有可能的二-O-乙酸盐和单-O-乙酸盐是通过使用脂肪酶的化学酶法制备的。2,3-二-O-乙酸盐可以90％的收率通过将C-indylylylracerace脂肪酶（CCL）或ruged rugosa脂肪酶（LAY）的过-O-乙酰化对硝基苯基α-L-阿拉伯呋喃糖苷的伯乙酰基脱乙酰化而获得）。在有机溶剂中，通过洋葱假单胞菌脂肪酶（LPS-30）对对硝基苯基α-L-阿拉伯呋喃糖苷进行乙酰化，可得到2,5-和3,5-二-O-乙酸酯。通过猪胰脂肪酶催化的对硝基苯基α-L-阿拉伯呋喃糖苷的乙酰化，以95％的产率区域选择性地合成5-O-乙酸盐。最后，分两步获得对硝基苯基α-L-阿拉伯呋喃糖苷的2-和3-O-乙酸盐。