1-oxo-2-methylpropylphosphonic acid | 67532-93-8

• 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: 1-oxo-2-methylpropylphosphonic acid
• 英文别名: (2-Methylpropanoyl)phosphonic acid；2-methylpropanoylphosphonic acid
• CAS: 67532-93-8
• 化学式: C₄H₉O₄P
• 分子量: 152.087
• InChiKey: TXXSHMJSGVBRDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  isobutyrylphosphonic acid dibenzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 生成 1-oxo-2-methylpropylphosphonic acid
  参考文献：
  名称：

  Synthesis of ?-ketophosphonic acids

  摘要：

  DOI：

  10.1007/bf00923378

文献信息

• Reaction of HppE with Substrate Analogues: Evidence for Carbon–Phosphorus Bond Cleavage by a Carbocation Rearrangement
  作者：Wei-chen Chang、Steven O. Mansoorabadi、Hung-wen Liu

  DOI：10.1021/ja403441x

  日期：2013.6.5

  (S)-2-hydroxypropylphosphonic acid ((S)-2-HPP) epoxidase (HppE) is an unusual mononuclear non-heme iron enzyme that catalyzes the oxidative epoxidation of (S)-2-HPP in the biosynthesis of the antibiotic fosfomycin. Recently, HppE has been shown to accept (R)-1-hydroxypropylphosphonic acid as a substrate and convert it to an aldehyde product in a reaction involving a biologically unprecedented 1,2-phosphono

  (S)-2-羟丙基膦酸 ((S)-2-HPP) 环氧化酶 (HppE) 是一种不寻常的单核非血红素铁酶，可在抗生素磷霉素的生物合成中催化 (S)-2-HPP 的氧化环氧化. 最近，HppE 已被证明接受 (R)-1-羟丙基膦酸作为底物，并在涉及生物学上前所未有的 1,2-膦酰基迁移的反应中将其转化为醛产物。在这项研究中，设计、合成了一系列底物类似物，并将其用作机械探针来研究这种新型酶促转化。所得数据以及从密度泛函理论计算中获得的见解与 HppE 催化的膦酰基迁移的机制一致，该机制涉及碳正离子中间体的形成。像这样，
• Bioconversion of aminophosphonates to hydroxyphosphonates<i>via</i>two step redox reactions employing fungi
  作者：Natalia Kmiecik、Paulina Majewska、Kinga Kozyra、Ewa Żymańczyk-Duda

  DOI：10.1080/10426507.2017.1395437

  日期：2018.4.3

  The conversion path and the complex procedure of products separation elaborated for ketophosphonates and hydroxyphosphonates formed during the biotransformations of aminophoshonates are reported. Penicillium funiculosum (Thom 3), Geotrichum candidum (6593), Beauveria bassiana (271B) were applied for bioconversion of a racemic mixture of the phosphonic analogue of isoleucine (Ile(P)), whereas P. funiculosum (Thom 3), F. oxysporum (DSM 12646) and Trigonopsis variabilis (DSM 70714) were used for transformation of the phosphonic analogue of valine (Val(P)). The biocatalytic processes were analysed to confirm and to compare the path and the selectivity of the biological conversion of aminophosphonates with one (Val(P)) and two stereogenic centers (Ile(P)). The efforts undertaken allowed to demonstrate, that applied biocatalysts act in two steps. A racemic mixture of substrates was bioconverted via oxidative deamination with formation of ketones, which were subsequently bioreduced in the next step of the process. As it was proved the selectivity of the bioreactions differs depending on the structure of the substrate. The first step of the process in the case of the phosphonic analogue of valine 4 allowed to obtain the pure unreacted enantiomer of aminophosphonate (R) whereas the biotransformation of Ile(P) was unselective. Both ketone intermediates were reduced in a non-selective way. The results were evaluated by NMR, MS and IR techniques, which confirmed the path of the biocatalytic two steps redox reaction: oxidation and reduction.[GRAPHICS].