1-deoxy-1-fluoro-D-xylulose-5-phosphate | 786709-64-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-deoxy-1-fluoro-D-xylulose-5-phosphate
• 英文别名: [(2R,3S)-5-fluoro-2,3-dihydroxy-4-oxopentyl] dihydrogen phosphate
• CAS: 786709-64-6
• 化学式: C₅H₁₀FO₇P
• 分子量: 232.102
• InChiKey: XQHSLGTXOCNQIE-RFZPGFLSSA-N

物化性质

• 沸点：
  561.5±60.0 °C(Predicted)
• 密度：
  1.720±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  124
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  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 1-deoxy-1-fluoro-D-xylulose-5-phosphate
  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

文献信息

• Study of 1-Deoxy-<scp>d</scp>-xylulose-5-phosphate Reductoisomerase:  Synthesis and Evaluation of Fluorinated Substrate Analogues
  作者：Alexander Wong、Jeffrey W. Munos、Vidusha Devasthali、Kenneth A. Johnson、Hung-wen Liu

  DOI：10.1021/ol048459b

  日期：2004.9.1

  1-Deoxy-D-xylulose-5-phosphate (DXP) reductoisomerase is a NADPH-dependent enzyme catalyzing the conversion of DXP to methyl-D-erythritol 4-phosphate (MEP). In this study, each of the hydroxyl groups in DXP and one of its C-1 hydrogen atoms, were separately replaced with a fluorine atom and the effect of the substitution on the catalytic turnover was examined. It was found that the 1-fluoro-DXP is a poor substrate, while both 3- and 4-fluoro-DXP behave as noncompetitive inhibitors.