(2R,3R)-4-hydorxy-3-methyl-2,3-epoxybutanyl diphosphate | 1196056-86-6

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机含氧阴离子化合物
• 英文名称: (2R,3R)-4-hydorxy-3-methyl-2,3-epoxybutanyl diphosphate
• 英文别名: (2R,3R)-4-hydroxy-3-methyl-2,3-epoxybutanyl diphosphate；[(2R,3R)-3-(hydroxymethyl)-3-methyloxiran-2-yl]methyl phosphono hydrogen phosphate
• CAS: 1196056-86-6
• 化学式: C₅H₁₂O₉P₂
• 分子量: 278.092
• InChiKey: QKDROOPEJBTSRH-RFZPGFLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.4
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  146
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (2R,3R)-4-hydorxy-3-methyl-2,3-epoxybutanyl diphosphate 在 IspG enzyme 作用下， 生成 2C-methyl-D-erythritol 2,4-O-cyclodiphosphate
  参考文献：
  名称：

  Methylerythritol cyclodiphosphate (MEcPP) in deoxyxylulose phosphate pathway: synthesis from an epoxide and mechanisms

  摘要：

  在这篇通讯中，我们报道了另一种独特的 IspG 催化转化，即当反应混合物中不使用还原剂时，IspG 从 (2R,3R)-4- 羟基-3-甲基-2,3-环氧丁酰二磷酸（环氧-HMBPP）生成其底物 MEcPP。

  DOI：

  10.1039/c0cc02594a
• 作为产物：
  描述：

  (2R,3R)-4-hydroxy-3-methyl-2,3-epoxybutanyl methanesulfonate 在 tris(tetra-n-butylammonium) hydrogen pyrophosphate 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以40%的产率得到(2R,3R)-4-hydorxy-3-methyl-2,3-epoxybutanyl diphosphate
  参考文献：
  名称：

  IspG Converts an Epoxide Substrate Analogue to (E)-4-Hydroxy-3-methylbut-2-enyl Diphosphate: Implications for IspG Catalysis in Isoprenoid Biosynthesis

  摘要：

  IspG is an intriguing enzyme in bacteria, parasite, and plant isoprenoid biosynthesis, and its catalytic mechanism remains elusive. We report here the synthesis of (2R,3R)-4-hydroxy-3-methyl-2,3-epoxybutanyl diphosphate (Epoxy-HMBPP), a proposed intermediate in one of the frequently cited mechanistic models. We have also demonstrated that this epoxide analogue is a catalytically competent IspG substrate. This study represents the first mechanistic study of this important enzyme.

  DOI：

  10.1021/ja907470n

文献信息

• IspG Converts an Epoxide Substrate Analogue to (<i>E</i>)-4-Hydroxy-3-methylbut-2-enyl Diphosphate: Implications for IspG Catalysis in Isoprenoid Biosynthesis
  作者：Rodney L. Nyland II、Youli Xiao、Pinghua Liu、Caren L. Freel Meyers

  DOI：10.1021/ja907470n

  日期：2009.12.16

  IspG is an intriguing enzyme in bacteria, parasite, and plant isoprenoid biosynthesis, and its catalytic mechanism remains elusive. We report here the synthesis of (2R,3R)-4-hydroxy-3-methyl-2,3-epoxybutanyl diphosphate (Epoxy-HMBPP), a proposed intermediate in one of the frequently cited mechanistic models. We have also demonstrated that this epoxide analogue is a catalytically competent IspG substrate. This study represents the first mechanistic study of this important enzyme.
• Methylerythritol cyclodiphosphate (MEcPP) in deoxyxylulose phosphate pathway: synthesis from an epoxide and mechanisms
  作者：Youli Xiao、Rodney L. Nyland II、Caren L. Freel Meyers、Pinghua Liu

  DOI：10.1039/c0cc02594a

  日期：——

  In this communication, we reported another unique IspG-catalyzed transformation, the production of its substrate, MEcPP, from (2R,3R)-4-hydroxy-3-methyl-2,3-epoxybutanyl diphosphate (Epoxy-HMBPP) when reductants are excluded from the reaction mixture.

  在这篇通讯中，我们报道了另一种独特的 IspG 催化转化，即当反应混合物中不使用还原剂时，IspG 从 (2R,3R)-4- 羟基-3-甲基-2,3-环氧丁酰二磷酸（环氧-HMBPP）生成其底物 MEcPP。