isobutyl p-nitrophenyl methylphosphonate | 7364-83-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: isobutyl p-nitrophenyl methylphosphonate
• 英文别名: isobutyl 4-nitrophenyl methylphosphonate；Methyl-phosphonsaeure-isobutylester-(4-nitro-phenylester)；1-[methyl(2-methylpropoxy)phosphoryl]oxy-4-nitrobenzene
• CAS: 7364-83-2
• 化学式: C₁₁H₁₆NO₅P
• 分子量: 273.226
• InChiKey: NPRXJVHIHPKOIL-UHFFFAOYSA-N

物化性质

• 沸点：
  141-142.5 °C(Press: 0.02 Torr)
• 密度：
  1.229±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.47
• 重原子数：
  18.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  78.67
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  isobutyl p-nitrophenyl methylphosphonate 在 5-(N-(hexadecyl)-N,N-dimethyl-N-(β-ethyloxy)ammonium)-2-iodosobenzoate 、 十六烷基三甲基氯化铵 作用下， 以 水 为溶剂， 生成 对硝基苯酚
  参考文献：
  名称：

  Efficient catalytic cleavage of reactive phosphates by a functionalized o-iodosobenzoate surfactant

  摘要：

  DOI：

  10.1021/ja00264a035
• 作为产物：
  描述：

  异丁醇 、 alkaline earth salt of/the/ methylsulfuric acid 在 乙醚 、 三乙胺 、 苯 作用下， 生成 isobutyl p-nitrophenyl methylphosphonate
  参考文献：
  名称：

  de Roos, Recueil des Travaux Chimiques des Pays-Bas, 1959, vol. 78, p. 145,148, 149

  摘要：

  DOI：

文献信息

• Molecular Engineering of Organophosphate Hydrolysis Activity from a Weak Promiscuous Lactonase Template
  作者：Monika M. Meier、Chitra Rajendran、Christoph Malisi、Nicholas G. Fox、Chengfu Xu、Sandra Schlee、David P. Barondeau、Birte Höcker、Reinhard Sterner、Frank M. Raushel

  DOI：10.1021/ja405911h

  日期：2013.8.7

  lactonase (PLL) family that show promiscuous organophosphate-degrading activity. Starting from a weakly promiscuous PLL scaffold (Dr0930 from Deinococcus radiodurans ), we designed an extremely efficient organophosphate hydrolase (OPH) with broad substrate specificity using rational and random mutagenesis in combination with in vitro activity screening. The OPH activity for seven organophosphate substrates

  酶的快速进化为蛋白质非凡的适应性提供了独特的分子见解，并有助于阐明氨基酸序列、结构和功能之间的关系。我们研究了来自 Pseudomonas diminuta (PdPTE) 的磷酸三酯酶的进化，该酶以显着的催化效率水解合成有机磷酸酯。PTE 被认为是一种进化上“年轻”的酶，据推测它是从磷酸三酯酶样内酯酶 (PLL) 家族的成员进化而来的，这些成员表现出混杂的有机磷降解活性。从弱混杂的 PLL 支架（来自耐辐射奇异球菌的 Dr0930）开始，我们使用合理和随机诱变结合体外活性筛选设计了一种具有广泛底物特异性的极其有效的有机磷酸酯水解酶 (OPH)。七个有机磷底物的 OPH 活性同时增强了多达 5 个数量级，实现了高达 10(6) M(-1) s(-1) 的催化效率的绝对值。结构和计算分析确定了工程化 PLL 变体增强 OPH 活性的分子基础，并证明 PdPTE 和工程化 PLL 中的 OPH
• Structural Characterization and Function Determination of a Nonspecific Carboxylate Esterase from the Amidohydrolase Superfamily with a Promiscuous Ability To Hydrolyze Methylphosphonate Esters
  作者：Dao Feng Xiang、Desigan Kumaran、Subramanyam Swaminathan、Frank M. Raushel

  DOI：10.1021/bi5004266

  日期：2014.6.3

  The uncharacterized protein Rsp3690 from Rhodobacter sphaeroides is a member of the amidohydrolase superfamily of enzymes. In this investigation the gene for Rsp3690 was expressed in Escherichia coli and purified to homogeneity, and the three-dimensional structure was determined to a resolution of 1.8 angstrom. The protein folds as a distorted (beta/alpha)(8)-barrel, and the subunits associate as a homotetramer. The active site is localized to the C-terminal end of the beta-barrel and is highlighted by the formation of a binuclear metal center with two manganese ions that are bridged by Glu-175 and hydroxide. The remaining ligands to the metal center include His-32, His-34, His-207, His-236, and Asp-302. Rsp3690 was shown to catalyze the hydrolysis of a wide variety of carboxylate esters, in addition to organophosphate and organophosphonate esters. The best carboxylate ester substrates identified for Rsp3690 included 2-naphthyl acetate (k(cat)/K-m = 1.0 x 10(5) M-1 s(-1)), 2-naphthyl propionate (k(cat)/K-m = 1.5 x 10(5) M-1 s(-1)), 1-naphthyl acetate (k(cat)/K-m = 7.5 x 10(3) M-1 s(-1)), 4-methylumbelliferyl acetate (k(cat)/K-m = 2.7 x 10(3) M-1 s(-1)), 4-nitrophenyl acetate (k(cat)/K-m = 2.3 x 10(5) M-1 s(-1)), and 4-nitrophenyl butyrate (k(cat)/K-m = 8.8 x 10(5) M-1 s(-1)). The best organophosphonate ester substrates included ethyl 4-nitrophenyl methylphosphonate (k(cat)/K-m = 3.8 x 10(5) M-1 s(-1)) and isobutyl 4-nitrophenyl methylphosphonate (k(cat)/K-m = 1.1 x 10(4) M-1 s(-1)). The (S-p)-enantiomer of isobutyl 4-nitrophenyl methylphosphonate was hydrolyzed 10 times faster than the less toxic (R-p)-enantiomer. The high inherent catalytic activity of Rsp3690 for the hydrolysis of the toxic enantiomer of methylphosphonate esters make this enzyme an attractive target for directed evolution investigations.
• Begunov, A. V.; Rutkovskii, G. V.; Kuznetsov, S. G., Journal of Organic Chemistry USSR (English Translation), 1981, p. 1486 - 1491
  作者：Begunov, A. V.、Rutkovskii, G. V.、Kuznetsov, S. G.

  DOI：——

  日期：——
• Rutkovskii, G. V.; Begunov, A. V.; Ignat'ev, Yu. A., Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, # 4, p. 701 - 705
  作者：Rutkovskii, G. V.、Begunov, A. V.、Ignat'ev, Yu. A.

  DOI：——

  日期：——