| 1417989-56-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• CAS: 1417989-56-0
• 化学式: C₂₂H₂₄ClF₃O₁₃
• 分子量: 588.873
• InChiKey: AJHXIILRZILZCL-LRZMXKANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.53
• 重原子数：
  39.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  208.74
• 氢给体数：
  7.0
• 氢受体数：
  13.0

反应信息

• 作为产物：
  描述：

  在 盐酸 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Rational design, synthesis, evaluation and enzyme-substrate structures of improved fluorogenic substrates for family 6 glycoside hydrolases

  摘要：

  Methylumbelliferyl‐β–cellobioside (MUF–G2) is a convenient fluorogenic substrate for certain β–glycoside hydrolases (GH). However, hydrolysis of the aglycone is poor with GH family 6 enzymes (GH6), despite strong binding. Prediction of the orientation of the aglycone of MUF–G2 in the +1 subsite of Hypocrea jecorina Cel6A by automated docking suggested umbelliferyl modifications at C4 and C6 for improved recognition. Four modified umbelliferyl‐β–cellobiosides [6–chloro‐4–methyl‐ (ClMUF); 6–chloro‐4‐trifluoromethyl‐ (ClF3MUF); 4–phenyl‐ (PhUF); 6–chloro‐4–phenyl‐ (ClPhUF)] were synthesized and tested with GH6, GH7, GH9, GH5 and GH45 cellulases. Indeed the rate of aglycone release by H. jecorina Cel6A was 10–150 times higher than with MUF–G2, although it was still three orders of magnitude lower than with H. jecorina Cel7B. The 4–phenyl substitution drastically reduced the fluorescence intensity of the free aglycone, while ClMUF–G2 could be used for determination of kcat and KM for H. jecorina Cel6A and Thermobifida fusca Cel6A. Crystal structures of H. jecorina Cel6A D221A mutant soaked with the MUF‐, ClMUF‐ and ClPhUF‐β–cellobioside substrates show that the modifications turned the umbelliferyl group ‘upside down’, with the glycosidic bond better positioned for protonation than with MUF–G2.DatabaseStructural data have been submitted to the Protein Data Bank under accession numbers pdb 4AU0, 4AX7, 4AX6Structured digital abstract• http://mint.bio.uniroma2.it/mint/search/interaction.do?interactionAc=MINT-7260296• Cel6A and Cel6A bind by x-ray crystallography (View Interaction: 1, 2)

  DOI：

  10.1111/febs.12060