(6-fluoromethyl-2',2',6-trimethyl-tetrahydrofuro[2,3-d]-1,3-dioxol-5-yl)-methanol | 1039054-32-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (6-fluoromethyl-2',2',6-trimethyl-tetrahydrofuro[2,3-d]-1,3-dioxol-5-yl)-methanol
• CAS: 1039054-32-4
• 化学式: C₁₀H₁₇FO₄
• 分子量: 220.241
• InChiKey: UDOVPTIKDOHLNE-IBCQBUCCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.83
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  47.92
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (6-fluoromethyl-2',2',6-trimethyl-tetrahydrofuro[2,3-d]-1,3-dioxol-5-yl)-methanol 、 三甲氧基磷 在 2,6-二甲基吡啶 、 四氯化碲 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以90%的产率得到phosphoric acid 6-fluoromethyl-2',2',6-trimethyl-tetrahydrofuro[2,3-d]-1,3-dioxol-5-ylmethyl ester dimethyl ester
  参考文献：
  名称：

  Synthesis and analysis of a fluorinated product analogue as an inhibitor for 1-deoxy-d-xylulose 5-phosphate reductoisomerase

  摘要：

  1-Deoxy-D-xylulose 5-phosphate (DXP) reductoisomerase (DXR) is an NADPH-dependent enzyme catalyzing the rearrangement and reduction of DXP to methyl-D-erythritol 4-phosphate ( MEP). Two mechanisms for this enzymatic reaction have been proposed, involving either an alpha-ketol rearrangement or a retroaldol/aldol rearrangement. In this study, a fluorinated product analogue, FCH(2)-MEP, was synthesized as a possible mechanism-based inactivator for DXR if the retroaldol/aldol mechanism is operative. FCH2-MEP was found to be a weak competitive inhibitor, and thus was unable to discriminate between the mechanisms. This result is due to the inability of the targeted enzyme, DXR, to oxidize FCH2-MEP to the aldehyde intermediate that is common to both mechanisms. While FCH2-MEP failed to act as a mechanism-based inactivator, the insight gained from this study will assist in the future design of inhibitors of DXR. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.11.062
• 作为产物：
  描述：

  C₁₀H₁₅FO₄ 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以24 mg的产率得到(6-fluoromethyl-2',2',6-trimethyl-tetrahydrofuro[2,3-d]-1,3-dioxol-5-yl)-methanol
  参考文献：
  名称：

  Synthesis and analysis of a fluorinated product analogue as an inhibitor for 1-deoxy-d-xylulose 5-phosphate reductoisomerase

  摘要：

  1-Deoxy-D-xylulose 5-phosphate (DXP) reductoisomerase (DXR) is an NADPH-dependent enzyme catalyzing the rearrangement and reduction of DXP to methyl-D-erythritol 4-phosphate ( MEP). Two mechanisms for this enzymatic reaction have been proposed, involving either an alpha-ketol rearrangement or a retroaldol/aldol rearrangement. In this study, a fluorinated product analogue, FCH(2)-MEP, was synthesized as a possible mechanism-based inactivator for DXR if the retroaldol/aldol mechanism is operative. FCH2-MEP was found to be a weak competitive inhibitor, and thus was unable to discriminate between the mechanisms. This result is due to the inability of the targeted enzyme, DXR, to oxidize FCH2-MEP to the aldehyde intermediate that is common to both mechanisms. While FCH2-MEP failed to act as a mechanism-based inactivator, the insight gained from this study will assist in the future design of inhibitors of DXR. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.11.062