dibenzyl [(3S,4R)-1-fluoro-2-hydroxy-3,4-(isopropylidenedioxy)pentan-5-yl] phosphate | 850144-22-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dibenzyl [(3S,4R)-1-fluoro-2-hydroxy-3,4-(isopropylidenedioxy)pentan-5-yl] phosphate
• CAS: 850144-22-8
• 化学式: C₂₂H₂₈FO₇P
• 分子量: 454.432
• InChiKey: CIBDWDMVNOETEB-RWLBOTFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  31.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  83.45
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  dibenzyl [(3S,4R)-1-fluoro-2-hydroxy-3,4-(isopropylidenedioxy)pentan-5-yl] phosphate 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 Phosphoric acid dibenzyl ester (4R,5S)-5-(2-fluoro-acetyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester 、 Phosphoric acid dibenzyl ester (4R,5S)-5-(2-fluoro-1,1-dihydroxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl 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：

  4-O-benzyl-2,3-O-isopropylidene-D-threose 在 palladium on activated charcoal 吡啶 、 氢气 、 碘 、 sodium hydride 、 fluorhydrate de diisopropylamine 作用下， 以 乙醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 25.0h， 生成 dibenzyl [(3S,4R)-1-fluoro-2-hydroxy-3,4-(isopropylidenedioxy)pentan-5-yl] 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