p-nitrophenyl 5-deoxy-α-L-arabinofuranoside | 953429-48-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-nitrophenyl 5-deoxy-α-L-arabinofuranoside
• 英文别名: (2S,3R,4R,5S)-2-methyl-5-(4-nitrophenoxy)oxolane-3,4-diol
• CAS: 953429-48-6
• 化学式: C₁₁H₁₃NO₆
• 分子量: 255.227
• InChiKey: FTGBVWARFYAYCB-HTCUVTCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  p-nitrophenyl 5-deoxy-α-L-arabinofuranoside 在 non-reducing end alpha-L-arabinofuranosidase 作用下， 以 水 为溶剂， 反应 1.0h， 以1 mg的产率得到p-nitrophenyl 5-deoxy-α-L-arabinofuranosyl-(1->2)-5-deoxy-α-L-arabinofuranoside
  参考文献：
  名称：

  Investigation of the specificity of an α-l-arabinofuranosidase using C-2 and C-5 modified α-l-arabinofuranosides

  摘要：

  The synthesis of three novel glycosyl donors presenting the same scaffold as alpha-L-arabinofuranose but modified at the C-2 or C-5 positions has been achieved. Furthermore, chemoenzymatic syntheses using the alpha-L-arabinofuranosidase AbfD3 and these unnatural furanosides were investigated. The use of the novel p-nitrophenyl furanoside donors revealed that AbfD3 can perform transglycosylation with the C-5 deoxygenated donor but not with the C-2 modified one. These results emphasize the vital role for OH-2 in AbfD3 substrate recognition. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.06.001
• 作为产物：
  描述：

  methyl-[O⁵-(toluene-4-sulfonyl)-α-L-arabinofuranoside] 在 吡啶 、 甲醇 、 sodium tetrahydroborate 、 硫酸 、 三氟化硼乙醚 、 sodium methylate 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 p-nitrophenyl 5-deoxy-α-L-arabinofuranoside
  参考文献：
  名称：

  Investigation of the specificity of an α-l-arabinofuranosidase using C-2 and C-5 modified α-l-arabinofuranosides

  摘要：

  The synthesis of three novel glycosyl donors presenting the same scaffold as alpha-L-arabinofuranose but modified at the C-2 or C-5 positions has been achieved. Furthermore, chemoenzymatic syntheses using the alpha-L-arabinofuranosidase AbfD3 and these unnatural furanosides were investigated. The use of the novel p-nitrophenyl furanoside donors revealed that AbfD3 can perform transglycosylation with the C-5 deoxygenated donor but not with the C-2 modified one. These results emphasize the vital role for OH-2 in AbfD3 substrate recognition. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.06.001

文献信息

• Investigation of the specificity of an α-l-arabinofuranosidase using C-2 and C-5 modified α-l-arabinofuranosides
  作者：Gérald Lopez、Caroline Nugier-Chauvin、Caroline Rémond、Michael O’Donohue

  DOI：10.1016/j.carres.2007.06.001

  日期：2007.11

  The synthesis of three novel glycosyl donors presenting the same scaffold as alpha-L-arabinofuranose but modified at the C-2 or C-5 positions has been achieved. Furthermore, chemoenzymatic syntheses using the alpha-L-arabinofuranosidase AbfD3 and these unnatural furanosides were investigated. The use of the novel p-nitrophenyl furanoside donors revealed that AbfD3 can perform transglycosylation with the C-5 deoxygenated donor but not with the C-2 modified one. These results emphasize the vital role for OH-2 in AbfD3 substrate recognition. (C) 2007 Elsevier Ltd. All rights reserved.