(S)-2-hydroxypropylphosphonic acid

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: (S)-2-hydroxypropylphosphonic acid
• 英文别名: [(2S)-2-hydroxypropyl]phosphonic acid
• 化学式: C₃H₉O₄P
• 分子量: 140.076
• InChiKey: ZFVCONUOLQASEW-VKHMYHEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2-hydroxypropylphosphonic acid 在 Streptomyces fradiae 作用下， 生成 磷霉素
  参考文献：
  名称：

  Simov, Biljana Peric; Wuggenig, Frank; Laemmerhofer, Michael, European Journal of Organic Chemistry, 2002, # 7, p. 1139 - 1142

  摘要：

  DOI：

文献信息

• Simov, Biljana Peric; Wuggenig, Frank; Laemmerhofer, Michael, European Journal of Organic Chemistry, 2002, # 7, p. 1139 - 1142
  作者：Simov, Biljana Peric、Wuggenig, Frank、Laemmerhofer, Michael、Lindner, Wolfgang、Zarbl, Elfriede、Hammerschmidt, Friedrich

  DOI：——

  日期：——
• Mechanistic Studies of HPP Epoxidase: Configuration of the Substrate Governs Its Enzymatic Fate
  作者：Zongbao Zhao、Pinghua Liu、Kazuo Murakami、Tomohisa Kuzuyama、Haruo Seto、Hung-wen Liu

  DOI：10.1002/1521-3773(20021202)41:23<4529::aid-anie4529>3.0.co;2-2

  日期：2002.12.2
• Protein Purification and Function Assignment of the Epoxidase Catalyzing the Formation of Fosfomycin
  作者：Pinghua Liu、Kazuo Murakami、Takayuki Seki、Xuemei He、Siu-Man Yeung、Tomohisa Kuzuyama、Haruo Seto、Hung-wen Liu

  DOI：10.1021/ja004153y

  日期：2001.5.1
• Evidence for Radical-Mediated Catalysis by HppE: A Study Using Cyclopropyl and Methylenecyclopropyl Substrate Analogues
  作者：Hui Huang、Wei-chen Chang、Pei-Jing Pai、Anthony Romo、Steven O. Mansoorabadi、David H. Russell、Hung-wen Liu

  DOI：10.1021/ja3078126

  日期：2012.10.3

  (S)-2-Hydroxypropylphosphonic acid epoxidase (HppE) is an unusual mononuclear iron enzyme that catalyzes the oxidative epoxidation of (S)-2-hydroxypropylphosphonic acid ((S)-HPP) in the biosynthesis of the antibiotic fosfomycin. HppE also recognizes (R)-2-hydroxypropylphosphonic acid ((R)-HPP) as a substrate and converts it to 2-oxo-propylphosphonic acid. To probe the mechanisms of these HppE-catalyzed oxidations, cyclopropyl- and methylenecyclopropyl-containing compounds were synthesized and studied as radical clock substrate analogues. Enzymatic assays indicated that the (S)- and (R)-isomers of the cyclopropyl-containing analogues were efficiently converted to epoxide and ketone products by HppE, respectively. In contrast, the ultrafast methylenecyclopropyl-containing probe inactivated HppE, consistent with a rapid radical-triggered ring-opening process that leads to enzyme inactivation. Taken together, these findings provide, for the first time, experimental evidence for the involvement of a C2-centered radical intermediate with a lifetime on the order of nanoseconds in the HppE-catalyzed oxidation of (R)-HPP.