(3R,4R)-1,2-epoxy-3,4-(isopropylidenedioxy)pentan-5-yl benzyl ether | 850144-19-3

• 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: (3R,4R)-1,2-epoxy-3,4-(isopropylidenedioxy)pentan-5-yl benzyl ether
• CAS: 850144-19-3
• 化学式: C₁₅H₂₀O₄
• 分子量: 264.321
• InChiKey: RYECRUPCUJLBMS-ILMHWDKJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.12
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  40.22
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (3R,4R)-1,2-epoxy-3,4-(isopropylidenedioxy)pentan-5-yl benzyl ether 在 palladium on activated charcoal 吡啶 、 氢气 、 碘 、 戴斯-马丁氧化剂 、 fluorhydrate de diisopropylamine 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 146.0h， 生成 Phosphoric acid mono-((2R,3S)-5-fluoro-2,3,4,4-tetrahydroxy-pentyl) ester
  参考文献：
  名称：

  Synthesis and Evaluation of 1-Deoxy-d-xylulose 5-Phosphoric Acid Analogues as Alternate Substrates for Methylerythritol Phosphate Synthase

  摘要：

  [GRAPHICS]Four deoxyxylulose phosphate (DXP) analogues were synthesized and evaluated as substrates/ inhibitors for methylerythritol phosphate (MEP) synthase. In analogues CF3-DXP (1), CF2-DXP (2), and CF-DXP (3), the three methyl hydrogens at Cl of DXP were sequentially replaced by fluorine. In the fourth analogue, Et-DXP (4), the methyl group in DXP was replaced by an ethyl moiety. Analogues 1, 2, and 4 were not substrates for MEP synthase under normal catalytic conditions and were instead modest inhibitors with IC50 values of 2.0, 3.4, and 6.2 mM, respectively. In contrast, 3 was a good substrate (k(cat) = 38 s(-1), K-m = 227 mu M) with a turnover rate similar to that of the natural substrate. These results are consistent with a retro-aldol/aldol mechanism rather than an a-ketol rearrangement for the enzyme-catalyzed conversion of DXP to MEP.

  DOI：

  10.1021/jo048022h
• 作为产物：
  描述：

  1-O-benzyl-2,3-O-isopropylidene-D-threitol 在 sodium hydride 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 0.75h， 生成 (3R,4R)-1,2-epoxy-3,4-(isopropylidenedioxy)pentan-5-yl benzyl ether
  参考文献：
  名称：

  Synthesis and Evaluation of 1-Deoxy-d-xylulose 5-Phosphoric Acid Analogues as Alternate Substrates for Methylerythritol Phosphate Synthase

  摘要：

  [GRAPHICS]Four deoxyxylulose phosphate (DXP) analogues were synthesized and evaluated as substrates/ inhibitors for methylerythritol phosphate (MEP) synthase. In analogues CF3-DXP (1), CF2-DXP (2), and CF-DXP (3), the three methyl hydrogens at Cl of DXP were sequentially replaced by fluorine. In the fourth analogue, Et-DXP (4), the methyl group in DXP was replaced by an ethyl moiety. Analogues 1, 2, and 4 were not substrates for MEP synthase under normal catalytic conditions and were instead modest inhibitors with IC50 values of 2.0, 3.4, and 6.2 mM, respectively. In contrast, 3 was a good substrate (k(cat) = 38 s(-1), K-m = 227 mu M) with a turnover rate similar to that of the natural substrate. These results are consistent with a retro-aldol/aldol mechanism rather than an a-ketol rearrangement for the enzyme-catalyzed conversion of DXP to MEP.

  DOI：

  10.1021/jo048022h