2,4-dinitrophenyl 3-O-acetyl-2-chloro-2-deoxy-β-D-xylopyranoside | 172218-59-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,4-dinitrophenyl 3-O-acetyl-2-chloro-2-deoxy-β-D-xylopyranoside
• CAS: 172218-59-6
• 化学式: C₁₃H₁₃ClN₂O₉
• 分子量: 376.707
• InChiKey: LGWHOQCAWXOIMM-XEZLXBQYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.14
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  151.27
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  2,3,4-三-O-乙酰基-1-O-(2,2,2-三氯亚氨代乙酰)-alpha-D-甘油-吡喃戊糖 、 2,4-dinitrophenyl 3-O-acetyl-2-chloro-2-deoxy-β-D-xylopyranoside 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以69%的产率得到2,4-dinitrophenyl 3,2',3',4'-tetra-O-acetyl-2-chloro-2-deoxy-β-D-xylobioside
  参考文献：
  名称：

  Syntheses and testing of substrates and mechanism-based inactivators for xylanases

  摘要：

  The syntheses of the 2,5- and 3,4-dinitrophenyl beta-xylobiosides by two separate routes are described, as well as the syntheses of the 2,4-dinitrophenyl beta-glycosides of 2-chloro-2-deoxyxylobiose and 2-deoxy-2-fluoro-xylobiose. Both the 3,4- and 2,5-dinitrophenyl beta-xylobiosides proved to be good substrates for the Bacillus subtilis xylanase, with k(cat)/K-m values of 1.0 and 34.4 mM(-1) s(-1), respectively. Excellent time-dependent inactivation of the exoxylanase/glucanase from Cellulomonas fimi was provided by 2,4-dinitrophenyl 2-deoxy-2-fluoro-beta-xylobioside,according to inactivation parameters of k(i) = 0.057 min(-1) and K-i = 0.0035 mM.

  DOI：

  10.1016/0008-6215(95)00080-d
• 作为产物：
  描述：

  2,4-dinitrophenyl 3,4-di-O-acetyl-2-chloro-2-deoxy-β-D-xylopyranoside 在 吡啶 、 氨 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 生成 2,4-dinitrophenyl 3-O-acetyl-2-chloro-2-deoxy-β-D-xylopyranoside
  参考文献：
  名称：

  Syntheses and testing of substrates and mechanism-based inactivators for xylanases

  摘要：

  The syntheses of the 2,5- and 3,4-dinitrophenyl beta-xylobiosides by two separate routes are described, as well as the syntheses of the 2,4-dinitrophenyl beta-glycosides of 2-chloro-2-deoxyxylobiose and 2-deoxy-2-fluoro-xylobiose. Both the 3,4- and 2,5-dinitrophenyl beta-xylobiosides proved to be good substrates for the Bacillus subtilis xylanase, with k(cat)/K-m values of 1.0 and 34.4 mM(-1) s(-1), respectively. Excellent time-dependent inactivation of the exoxylanase/glucanase from Cellulomonas fimi was provided by 2,4-dinitrophenyl 2-deoxy-2-fluoro-beta-xylobioside,according to inactivation parameters of k(i) = 0.057 min(-1) and K-i = 0.0035 mM.

  DOI：

  10.1016/0008-6215(95)00080-d