4-nitrophenoxymethyl 2-phthalimido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside | 1353638-96-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-nitrophenoxymethyl 2-phthalimido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside
• 英文别名: [(2R,3S,4R,5R,6S)-3,4-diacetyloxy-5-(1,3-dioxoisoindol-2-yl)-6-[(4-nitrophenoxy)methoxy]oxan-2-yl]methyl acetate
• CAS: 1353638-96-6
• 化学式: C₂₇H₂₆N₂O₁₃
• 分子量: 586.509
• InChiKey: ROCTTYLSWIXEMU-XMPCBSOPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  42
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  190
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  4-nitrophenoxymethyl 2-phthalimido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 在 吡啶 、 乙二胺 作用下， 以 正丁醇 为溶剂， 反应 20.0h， 生成 4-nitrophenoxymethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Chromogenic Carbamate and Acetal Substrates for Glycosaminidases

  摘要：

  The enzyme Dispersin B is a medicinally relevant beta-hexosaminidase with potential for use in the treatment of biofilm-related infections. Here we describe the synthesis and evaluation of a p-nitrophenyl glycosyl carbamate and a p-nitrophenyl glycosyl acetal as improved substrates of Dispersin B. The p-nitrophenyl glycosyl carbamate shows substantially improved analytical signal in continuous assays and superior kinetics (k(cat)/K-m 6.1 mM(-1) s(-1)) when compared to the benchmark substrate 4-nitrophenyl N-acetyl-beta-D-glucosaminide (k(cat)/K-m 0.021 mM(-1) s(-1)) in measuring Dispersin B activity. The improvements observed are compared to the activity of jack bean beta-hexosaminidase toward these substrates.

  DOI：

  10.1080/07328303.2011.610543
• 作为产物：
  描述：

  1-((甲硫基)甲氧基)-4-硝基苯 在 氯化亚砜 、 potassium carbonate 、 sodium iodide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 16.0h， 生成 4-nitrophenoxymethyl 2-phthalimido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Chromogenic Carbamate and Acetal Substrates for Glycosaminidases

  摘要：

  The enzyme Dispersin B is a medicinally relevant beta-hexosaminidase with potential for use in the treatment of biofilm-related infections. Here we describe the synthesis and evaluation of a p-nitrophenyl glycosyl carbamate and a p-nitrophenyl glycosyl acetal as improved substrates of Dispersin B. The p-nitrophenyl glycosyl carbamate shows substantially improved analytical signal in continuous assays and superior kinetics (k(cat)/K-m 6.1 mM(-1) s(-1)) when compared to the benchmark substrate 4-nitrophenyl N-acetyl-beta-D-glucosaminide (k(cat)/K-m 0.021 mM(-1) s(-1)) in measuring Dispersin B activity. The improvements observed are compared to the activity of jack bean beta-hexosaminidase toward these substrates.

  DOI：

  10.1080/07328303.2011.610543