4-nitrophenylcarbamoyl 2-acetamido-2-deoxy-β-D-glucopyranoside | 1353639-00-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-nitrophenylcarbamoyl 2-acetamido-2-deoxy-β-D-glucopyranoside
• 英文别名: [(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl] N-(4-nitrophenyl)carbamate
• CAS: 1353639-00-5
• 化学式: C₁₅H₁₉N₃O₉
• 分子量: 385.331
• InChiKey: HTBDKFDPNCDWIC-KSTCHIGDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  183
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-nitrophenylcarbamoyl 2-acetamido-2-deoxy-β-D-glucopyranoside 在 氯化亚砜 、 jack-bean β-hexosaminidase 、 水 、 sodium hydride 、 sodium iodide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 1-(氯甲氧基)-4-硝基苯
  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：

  2-deoxy-2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranose 在 一水合肼 、 三乙胺 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 10.0h， 生成 4-nitrophenylcarbamoyl 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.