2-Naphthol glucuronide | 6159-74-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Naphthol glucuronide
• 英文别名: 1-naphthol-β-D-glucuronide；β-naphthyl glucuronide；4-MU；O¹-[2]naphthyl-β-D-glucopyranuronic acid；O¹-[2]Naphthyl-β-D-glucopyranuronsaeure；<2>Naphthyl-β-D-glucuronid；Glucopyranosiduronic acid, 2-naphthyl, beta-D-；(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-naphthalen-2-yloxyoxane-2-carboxylic acid
• CAS: 6159-74-6
• 化学式: C₁₆H₁₆O₇
• 分子量: 320.299
• InChiKey: GIRALEWNTWEAKH-JHZZJYKESA-N

物化性质

• 熔点：
  100 °C(Solv: water (7732-18-5))
• 沸点：
  623.0±55.0 °C(Predicted)
• 密度：
  1.567±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 乙酸酐 、 2-Naphthol glucuronide 在 吡啶 、 甲醇 、 乙醚 作用下， 生成 2-PHTHYL-2,3,4-TRI-O-ACETYL-Β-D-GLUCURONICACIDMETHYLESTER2-萘基-2,3,4-三-O-乙酰基-Β-D-葡糖醛酸甲酯
  参考文献：
  名称：

  Corner et al., Biochemical Journal, 1954, vol. 56, p. 270,272

  摘要：

  DOI：
• 作为产物：
  描述：

  2-萘基-β-D-吡喃葡糖苷 在 氧气 、 碳酸氢钠 、 铂 作用下， 生成 2-Naphthol glucuronide
  参考文献：
  名称：

  Synthesis of 2-Naphthyl β-D-Glucopyruronoside and 2-Naphthyl β-D-Glucofururonolactone and their Behavior toward β-D-Glucuronidase¹

  摘要：

  DOI：

  10.1021/ja01142a019

文献信息

• UDP-Glucuronic Acid Binds First and the Aglycone Substrate Binds Second to Form a Ternary Complex in UGT1A9-Catalyzed Reactions, in Both the Presence and Absence of Bovine Serum Albumin
  作者：Nenad Manevski、Jari Yli-Kauhaluoma、Moshe Finel

  DOI：10.1124/dmd.112.047746

  日期：2012.11

  The presence of bovine serum albumin (BSA) largely modulates the enzyme kinetics parameters of the human UDP-glucuronosyltransferase (UGT) 1A9, increasing both the apparent aglycone substrate affinity of the enzyme and its limiting reaction velocity ( Drug Metab Dispos 39: 2117–2129, 2011). For a better understanding of the BSA effects and an examination of whether its presence changes the catalytic mechanism, we have studied the enzyme kinetics of 4-methylumbelliferone glucuronidation by UGT1A9 in the presence and absence of 0.1% BSA, using bisubstrate enzyme kinetic experiments, in both the forward and reverse directions, as well as product and dead-end inhibition. The combined results strongly suggest that the reaction mechanism of UGT1A9, and presumably other human UGTs as well, involves the formation of a compulsory-order ternary-complex, with UDP-α-d-glucuronic acid (UDPGA) as the first binding substrate. Based on the enzyme kinetic parameters measured for the forward and reverse reactions, the equilibrium constant of the overall reaction was calculated ( K eq = 574) and the relative magnitudes of the reaction rate constants were elucidated. The inclusion of BSA in the bisubstrate kinetic experiments quantitatively changed the apparent enzyme kinetic parameters, presumably by removing internal inhibitors that bind to the binary enzyme-UDPGA (E-UDPGA) complex, as well as to the ternary E-UDPGA-aglycone complex. Nevertheless, the underlying compulsory-order ternary-complex mechanism with UDPGA binding first is the same in both the absence and presence of BSA. The results offer a novel understanding of UGT enzyme kinetic mechanism and BSA effects.

  牛血清白蛋白(BSA)的存在显著调节了人尿苷二磷酸-葡萄糖醛酸基转移酶(UGT) 1A9的酶动力学参数，增加了酶对糖苷配基底物的表观亲和力及其极限反应速度(Drug Metab Dispos 39: 2117–2129, 2011)。为了更好地理解BSA效应并检验其存在是否改变催化机制，我们通过双底物酶动力学实验，分别在正反两个方向以及产物和死端抑制的条件下，研究了在0.1% BSA存在与否的情况下，UGT1A9对4-甲基伞形酮葡萄糖苷酸化的酶动力学。综合结果强烈表明，UGT1A9反应机制，以及可能其他人类UGT也是如此，涉及形成一个强制顺序的三元复合物，其中UDP-α-d-葡萄糖醛酸(UDPGA)是第一个结合的底物。根据测得的正反反应的酶动力学参数，计算出整个反应的平衡常数(Keq = 574)并阐明了反应速率常数的相对大小。在双底物动力学实验中加入BSA，通过去除与二元酶-UDPGA(E-UDPGA)复合物以及三元E-UDPGA-糖苷配基复合物结合的内部抑制剂，定量地改变了表观酶动力学参数。然而，无论BSA是否存在，其基础的强制顺序三元复合物机制以及UDPGA首先结合的情况是相同的。这些结果为我们提供了一种新的理解UGT酶动力学机制及BSA效应的视角。
• Method for detecting Escherichia coli in a sample
  申请人：3M INNOVATIVE PROPERTIES COMPANY

  公开号：US10023898B2

  公开（公告）日：2018-07-17

  A method of detecting Listeria monocytogenes. The method comprises providing a culture device with a selective culture medium and a detection article comprising a first indicator system. The selective culture medium facilitates the growth of Listeria microorganisms. When a Listeria microorganism is detected in a sample contacted with the culture medium, the detection article is contacted with the culture medium to detect Listeria monocytogenes.

  一种检测李斯特菌的方法。该方法包括提供一个带有选择性培养基的培养装置和一个包含第一指示系统的检测物品。选择性培养基有利于李斯特菌微生物的生长。当在与培养基接触的样品中检测到李斯特菌微生物时，检测物品与培养基接触以检测单增李斯特菌。
• Method for detecting a Shigella or Cronobacter microorganism
  申请人：3M INNOVATIVE PROPERTIES COMPANY

  公开号：US10619181B2

  公开（公告）日：2020-04-14

  A method of detecting a Shigella or Cronobacter microorganism. The method comprises providing a culture device with a selective culture medium and a detection article comprising a first indicator system.

  一种检测志贺氏菌或克罗诺斯菌微生物的方法。该方法包括提供一个带有选择性培养基的培养装置和一个包含第一指示系统的检测物品。
• The Synthesis of Aryl-D-glucopyranosiduronic Acids¹
  作者：G. N. Bollenback、John W. Long、D. G. Benjamin、J. A. Lindquist

  DOI：10.1021/ja01617a047

  日期：1955.6
• Tsukamoto et al., Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1956, vol. 76, p. 1282,1286
  作者：Tsukamoto et al.

  DOI：——

  日期：——