dibenzyl (4S,5R)-3-oxo-4,5-(isopropylidenedioxy)hexan-6-yl phosphate | 850144-26-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: dibenzyl (4S,5R)-3-oxo-4,5-(isopropylidenedioxy)hexan-6-yl phosphate
• 英文别名: dibenzyl [(4R,5S)-2,2-dimethyl-5-propanoyl-1,3-dioxolan-4-yl]methyl phosphate
• CAS: 850144-26-2
• 化学式: C₂₃H₂₉O₇P
• 分子量: 448.453
• InChiKey: BIFKLPWPMXOSRF-FGZHOGPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  dibenzyl (4S,5R)-3-oxo-4,5-(isopropylidenedioxy)hexan-6-yl phosphate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 水 为溶剂， 反应 54.0h， 以99%的产率得到(4S,5R)-3-oxo-4,5-dihydroxyhex-6-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
• 作为产物：
  描述：

  (2S,3R)-2,3-(isopropylidenedioxy)-N-methoxy-N-methylbutanamide 在 吡啶 、 碘 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 dibenzyl (4S,5R)-3-oxo-4,5-(isopropylidenedioxy)hexan-6-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

文献信息

• Synthesis and Evaluation of 1-Deoxy-<scp>d</scp>-xylulose 5-Phosphoric Acid Analogues as Alternate Substrates for Methylerythritol Phosphate Synthase
  作者：David T. Fox、C. Dale Poulter

  DOI：10.1021/jo048022h

  日期：2005.3.1

  [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.