二甲基(2-羟丙基)膦酸酯 | 54731-75-8

• 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
• 中文名称: 二甲基(2-羟丙基)膦酸酯
• 英文名称: dimethyl (2-hydroxypropyl)phosphonate
• 英文别名: Dimethyl 2-hydroxypropylphosphonate；1-dimethoxyphosphorylpropan-2-ol
• CAS: 54731-75-8
• 化学式: C₅H₁₃O₄P
• 分子量: 168.13
• InChiKey: HUFBGIJJBISULH-UHFFFAOYSA-N

物化性质

• 沸点：
  92 °C(Press: 0.03 Torr)
• 密度：
  1.152±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  二甲基(2-羟丙基)膦酸酯 在 三甲基溴硅烷 、 烯丙基三甲基硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 (R,S)-(2-Hydroxypropyl)phosphonsaeure
  参考文献：
  名称：

  Initial characterization of Fom3 from Streptomyces wedmorensis: The methyltransferase in fosfomycin biosynthesis

  摘要：

  Fosfomycin is a broad-spectrum antibiotic that is useful against multi-drug resistant bacteria. Although its biosynthesis was first studied over 40 years ago, characterization of the penultimate methyl transfer reaction has eluded investigators. The enzyme believed to catalyze this reaction, Fom3, has been identified as a radical S-adenosyl-L-methionine (SAM) superfamily member. Radical SAM enzymes use SAM and a four-iron, four-sulfur ([4Fe-4S]) cluster to catalyze complex chemical transformations. Fom3 also belongs to a family of radical SAM enzymes that contain a putative cobalamin-binding motif, suggesting that it uses cobalamin for methylation. Here we describe the first biochemical characterization of Fom3 from Streptomyces wedmorensis. Since recombinant Fom3 is insoluble, we developed a successful refolding and iron-sulfur cluster reconstitution procedure. Spectroscopic analyses demonstrate that Fom3 binds a [4Fe-4S] cluster which undergoes a transition between a +2 "resting" state and a +1 active state characteristic of radical SAM enzymes. Site-directed mutagenesis of the cysteine residues in the radical SAM CxxxCxxC motif indicates that each residue is essential for functional cluster formation. We also provide preliminary evidence that Fom3 adds a methyl group to 2-hydroxyethylphosphonate (2-HEP) to form 2-hydroxypropylphosphonate (2-HPP) in an apparently SAM-, sodium dithionite-, and methylcobalamin-dependent manner. (C) 2013 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.abb.2013.12.004
• 作为产物：
  描述：

  丙酮基膦酸二甲酯 在 甲醇 、 sodium tetrahydroborate 作用下， 反应 1.0h， 生成 二甲基(2-羟丙基)膦酸酯
  参考文献：
  名称：

  Initial characterization of Fom3 from Streptomyces wedmorensis: The methyltransferase in fosfomycin biosynthesis

  摘要：

  Fosfomycin is a broad-spectrum antibiotic that is useful against multi-drug resistant bacteria. Although its biosynthesis was first studied over 40 years ago, characterization of the penultimate methyl transfer reaction has eluded investigators. The enzyme believed to catalyze this reaction, Fom3, has been identified as a radical S-adenosyl-L-methionine (SAM) superfamily member. Radical SAM enzymes use SAM and a four-iron, four-sulfur ([4Fe-4S]) cluster to catalyze complex chemical transformations. Fom3 also belongs to a family of radical SAM enzymes that contain a putative cobalamin-binding motif, suggesting that it uses cobalamin for methylation. Here we describe the first biochemical characterization of Fom3 from Streptomyces wedmorensis. Since recombinant Fom3 is insoluble, we developed a successful refolding and iron-sulfur cluster reconstitution procedure. Spectroscopic analyses demonstrate that Fom3 binds a [4Fe-4S] cluster which undergoes a transition between a +2 "resting" state and a +1 active state characteristic of radical SAM enzymes. Site-directed mutagenesis of the cysteine residues in the radical SAM CxxxCxxC motif indicates that each residue is essential for functional cluster formation. We also provide preliminary evidence that Fom3 adds a methyl group to 2-hydroxyethylphosphonate (2-HEP) to form 2-hydroxypropylphosphonate (2-HPP) in an apparently SAM-, sodium dithionite-, and methylcobalamin-dependent manner. (C) 2013 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.abb.2013.12.004

文献信息

• Kinetic resolution of hydroxyalkanephosphonates catalyzed by Candida antarctica lipase B in organic media
  作者：Yonghui Zhang、Chengye Yuan、Zuyi Li

  DOI：10.1016/s0040-4020(02)00229-6

  日期：2002.4

  A series of hydroxyalkanephosphonates were studied as substrates for CALB catalyzed acetylation with emphasis on enantioselectivity and chemical structure of substrates. Some hydroxyalkanephosphonates could be resolved successfully to give both (R)- and (S)-isomers with high enantiomeric excess.

  研究了一系列羟基链烷膦酸酯作为CALB催化乙酰化反应的底物，重点是底物的对映选择性和化学结构。一些羟基链烷膦酸酯可以成功地拆分，以得到具有高对映体过量的（R）-和（S）-异构体。
• Preparation of phosphorus-organic esters
  申请人：Hoechst Aktiengesellschaft

  公开号：US03962378A1

  公开（公告）日：1976-06-08

  2-Hydroxyethane-phosphonic acid diesters, 2-hydroxyethylphoshinic acid esters and the corresponding thiophoshonic acid-O,O-diesters or thiophosphinic acid-O-esters of the formula ##EQU1## wherein R.sub.1 is alkyl having from 1 to 18 carbon atoms, R.sub.2 has the meaning of R.sub.1 or represents cycloalkyl having up to 10 carbon atoms, alkenyl having up to 18 carbon atoms, aryl having up to 14 carbon atoms or aralkyl having up to 15 carbon atoms, R.sub.3 means hydrogen, alkyl having up to 18 carbon atoms, alkenyl having up to 18 carbon atoms, cycloalkyl having up to 10 carbon atoms, aryl having up to 14 carbon atoms or aralkyl having up to 15 carbon atoms, the substituents R.sub.1 -R.sub.3 optionally being substituted, X represents oxygen or sulfur and n represents either 0 or 1, are prepared from 2-acyloxyethane-phosphonic acid diesters, 2-acyloxy-ethyl-phoshinic acid esters or the corresponding thiophoshonic acid-O,O-diesters or thiophoshinic acid-O-esters and are important intermediate products for the preparation of plant protecting agents and flame-proofing agents.

  2-羟基乙基磷酸二酯、2-羟基乙基膦酸酯和相应的巯基磷酸-O,O-二酯或巯基膦酸-O-酯的化学式为##EQU1##其中R.sub.1为1至18个碳原子的烷基，R.sub.2的含义为R.sub.1或表示具有最多10个碳原子的环烷基，具有最多18个碳原子的烯基，具有最多14个碳原子的芳基或具有最多15个碳原子的芳基烷基，R.sub.3表示氢、具有最多18个碳原子的烷基、具有最多18个碳原子的烯基、具有最多10个碳原子的环烷基、具有最多14个碳原子的芳基或具有最多15个碳原子的芳基烷基，取代基R.sub.1-R.sub.3是可选的，X表示氧或硫，n表示0或1。这些化合物是从2-酰氧基乙基磷酸二酯、2-酰氧基乙基膦酸酯或相应的巯基磷酸-O,O-二酯或巯基膦酸-O-酯制备而成，是制备植物保护剂和阻燃剂的重要中间体。
• BCL-2/BCL-XL INHIBITORS AND THERAPEUTIC METHODS USING THE SAME
  申请人：THE REGENTS OF THE UNIVERSITY OF MICHIGAN

  公开号：US20150336994A1

  公开（公告）日：2015-11-26

  Inhibitors of Bcl-2/Bcl-xL and compositions containing the same are disclosed. Methods of using the Bcl-2/Bcl-xL inhibitors in the treatment of diseases and conditions wherein inhibition of Bcl-2/Bcl-xL provides a benefit, like cancers, also are disclosed.

  揭示了Bcl-2/Bcl-xL抑制剂及含有它们的组合物。还揭示了使用Bcl-2/Bcl-xL抑制剂治疗疾病和情况的方法，其中抑制Bcl-2/Bcl-xL提供益处，例如癌症。
• Bcl-2/Bcl-xL inhibitors and therapeutic methods using the same
  申请人：THE REGENTS OF THE UNIVERSITY OF MICHIGAN

  公开号：US09403856B2

  公开（公告）日：2016-08-02

  Inhibitors of Bcl-2/Bcl-xL and compositions containing the same are disclosed. Methods of using the Bcl-2/Bcl-xL inhibitors in the treatment of diseases and conditions wherein inhibition of Bcl-2/Bcl-xL provides a benefit, like cancers, also are disclosed.

  本发明揭示了Bcl-2/Bcl-xL的抑制剂和含有它们的组合物。还揭示了使用Bcl-2/Bcl-xL抑制剂治疗疾病和情况的方法，其中Bcl-2/Bcl-xL的抑制提供了益处，例如癌症。
• An Efficient Route to Chiral α- and β-Hydroxyalkanephosphonates
  作者：Oscar Pàmies、Jan-E. Bäckvall

  DOI：10.1021/jo026888m

  日期：2003.6.1

  Enzymatic kinetic resolution of alpha- and beta-hydroxyphosphonates in combination with ruthenium-catalyzed alcohol isomerization led to a successful dynamic kinetic resolution. A variety of racemic hydroxyphosphonates were efficiently transformed to the corresponding enantiomerically pure acetates (ee up to 99% and yield up to 87%).