4-nitrophenoxymethyl 2-acetamido-2-deoxy-β-D-glucopyranoside | 1353638-98-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-nitrophenoxymethyl 2-acetamido-2-deoxy-β-D-glucopyranoside
• 英文别名: N-[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[(4-nitrophenoxy)methoxy]oxan-3-yl]acetamide
• CAS: 1353638-98-8
• 化学式: C₁₅H₂₀N₂O₉
• 分子量: 372.332
• InChiKey: DTAGZNCFGWTVAO-KJWHEZOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  163
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  4-硝基苯基-2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖苷 在 吡啶 、 氯化亚砜 、 jack-bean β-hexosaminidase 、 水 、 sodium methylate 、 sodium hydride 、 potassium carbonate 、 乙二胺 、 sodium iodide 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 、 正丁醇 为溶剂， 反应 42.0h， 生成 4-nitrophenoxymethyl 2-acetamido-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

文献信息

• Chromogenic Carbamate and Acetal Substrates for Glycosaminidases
  作者：Anthony Chibba、Somnath Dasgupta、Nandadeva Yakandawala、Srinivasa Madhyastha、Mark Nitz

  DOI：10.1080/07328303.2011.610543

  日期：2011.9.1

  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.