(R)-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: (R)-2-hydroxypropylphosphonic acid
• 英文别名: (2R)-hydroxypropylphosphonic acid；[(2r)-2-Hydroxypropyl]phosphonic Acid
• 化学式: C₃H₉O₄P
• 分子量: 140.076
• InChiKey: ZFVCONUOLQASEW-GSVOUGTGSA-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：

  (R)-2-hydroxypropylphosphonic acid 在 2-hydroxypropylphosphonic acid epoxidase 1,4-dihydronicotinamide adenine dinucleotide 、 flavin minonucleotide 、 氧气 作用下， 以 水 为溶剂， 反应 0.5h， 生成 acetonylphosphonic acid
  参考文献：
  名称：

  Mechanistic Studies of HPP Epoxidase: Configuration of the Substrate Governs Its Enzymatic Fate

  摘要：

  DOI：

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

文献信息

• Hydroperoxylation by Hydroxyethylphosphonate Dioxygenase
  作者：John T. Whitteck、Robert M. Cicchillo、Wilfred A. van der Donk

  DOI：10.1021/ja906238r

  日期：2009.11.11

  Hydroxyethylphosphonate dioxygenase (HEPD) catalyzes the O-2-dependent cleavage of the carbon-carbon bond of 2-hydroxyethylphosphonate (2-HEP) to afford hydroxymethylphosphonate (HMP) and formate without input of electrons or use of any organic cofactors. Two mechanisms have been proposed to account for this reaction. One involves initial hydroxylation of substrate to an acetal intermediate and its subsequent attack onto an Fe(IV)-oxo species. The second mechanism features initial hydroperoxylation of substrate followed by a Criegee rearrangement. To distinguish between the two mechanisms, substrate analogues were synthesized and presented to the enzyme. Hydroxymethylphosphonate was converted into phosphate and formate, and 1 -hydroxyethylphosphonate was converted to acetylphosphate, which is an inhibitor of the enzyme. These results provide strong support for a Criegee rearrangement with a phosphorus-based migrating group and require that the O-O bond of molecular oxygen is not cleaved prior to substrate activation. (2R)-Hydroxypropylphosphonate partitioned between conversion to 2-oxopropylphosphonate and hydroxymethylphosphonate, with the latter in turn converted to phosphate and formate. Collectively, these results support a mechanism that proceeds by hydroperoxylation followed by a Criegee rearrangement.
• 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