3-Chlorophenyl sulfate | 3233-54-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机硫酸及其衍生物
• 英文名称: 3-Chlorophenyl sulfate
• 英文别名: sulfuric acid mono-(3-chloro-phenyl ester)；Schwefelsaeure-mono-(3-chlor-phenylester)；(3-Chlor-phenyl)-hydrogensulfat；Mono-(3-chlor-phenyl)-sulfat；(3-Chlorophenyl) hydrogen sulfate
• CAS: 3233-54-3
• 化学式: C₆H₅ClO₄S
• 分子量: 208.622
• InChiKey: CJXHYODEJGJQKF-UHFFFAOYSA-N

物化性质

• 密度：
  1.637±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  72
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-Chlorophenyl sulfate 在 alkaline phosphatase 作用下， 以 various solvent(s) 为溶剂， 生成 sodium m-chlorophenoxide
  参考文献：
  名称：

  Do Electrostatic Interactions with Positively Charged Active Site Groups Tighten the Transition State for Enzymatic Phosphoryl Transfer?

  摘要：

  The effect of electrostatic interactions on the transition-state character for enzymatic phosphoryl transfer has been a subject of much debate. In this work, we investigate the transition state for alkaline phosphatase (AP) using linear free-energy relationships (LIFERs). We determined k(cat)/K-M for a series of aryl sulfate ester monoanions to obtain the Bronsted coefficient, beta(lg)., and compared the value to that obtained previously for a series of aryl phosphorothioate ester dianion substrates. Despite the difference in substrate charge, the observed Bronsted coefficients for AP-catalyzed aryl sulfate and aryl phosphorothioate hydrolysis (-0.76 +/- 0.14 and -0.77 +/- 0.10, respectively) are strikingly similar, with steric effects being responsible for the uncertainties in these values. Aryl sulfates and aryl phosphates react via similar loose transition states in solution. These observations suggest an apparent equivalency of the transition states for phosphorothioate and sulfate hydrolysis reactions at the AP active site and, thus, negligible effects of active site electrostatic interactions on charge distribution in the transition state.

  DOI：

  10.1021/ja0480421
• 作为产物：
  描述：

  3-氯苯酚 在 吡啶 、 氯磺酸 、 氯仿 作用下， 生成 3-Chlorophenyl sulfate
  参考文献：
  名称：

  Neuberg; Wagner, Biochemische Zeitschrift, 1925, vol. 161, p. 501

  摘要：

  DOI：

文献信息

• Neuberg; Wagner, Biochemische Zeitschrift, 1925, vol. 161, p. 501
  作者：Neuberg、Wagner

  DOI：——

  日期：——
• Do Electrostatic Interactions with Positively Charged Active Site Groups Tighten the Transition State for Enzymatic Phosphoryl Transfer?
  作者：Ivana Nikolic-Hughes、Douglas C. Rees、Daniel Herschlag

  DOI：10.1021/ja0480421

  日期：2004.9.1

  The effect of electrostatic interactions on the transition-state character for enzymatic phosphoryl transfer has been a subject of much debate. In this work, we investigate the transition state for alkaline phosphatase (AP) using linear free-energy relationships (LIFERs). We determined k(cat)/K-M for a series of aryl sulfate ester monoanions to obtain the Bronsted coefficient, beta(lg)., and compared the value to that obtained previously for a series of aryl phosphorothioate ester dianion substrates. Despite the difference in substrate charge, the observed Bronsted coefficients for AP-catalyzed aryl sulfate and aryl phosphorothioate hydrolysis (-0.76 +/- 0.14 and -0.77 +/- 0.10, respectively) are strikingly similar, with steric effects being responsible for the uncertainties in these values. Aryl sulfates and aryl phosphates react via similar loose transition states in solution. These observations suggest an apparent equivalency of the transition states for phosphorothioate and sulfate hydrolysis reactions at the AP active site and, thus, negligible effects of active site electrostatic interactions on charge distribution in the transition state.