(2-hydroxy-4-oxobutoxy)phosphonate

• 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: (2-hydroxy-4-oxobutoxy)phosphonate
• 英文别名: (2-Hydroxy-4-oxobutyl) dihydrogen phosphate；(2-hydroxy-4-oxobutyl) dihydrogen phosphate
• 化学式: C₄H₉O₆P
• 分子量: 184.086
• InChiKey: LQIRHIGPILJQHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  磷烯醇丙酮酸 、 (2-hydroxy-4-oxobutoxy)phosphonate 在 manganese(II) sulfate 、 Pyrococcus furiosus (type Iβ) 3-deoxy-D-arabino-heptulosonate 7-phosphate synthase 作用下， 生成 3-deoxy-D-arabino-2-heptulosonic acid 7-phosphate 、 3-deoxy-L-arabino-heptulosonate 7-phosphate
  参考文献：
  名称：

  Investigating the role of the hydroxyl groups of substrate erythrose 4-phosphate in the reaction catalysed by the first enzyme of the shikimate pathway

  摘要：

  3-Deoxy-D-arabino-heptulosonate 7-phosphate (DAH7P) synthase catalyses the first step of the shikimate pathway, which is responsible for the biosynthesis of aromatic amino acids in microorganisms and plants. This enzyme catalyses an aldol reaction between phosphoenolpyruvate and D-erythrose 4-phosphate to generate DAH7P. Both 2-deoxyerythrose 4-phosphate and 3-deoxyerythrose 4-phosphate were synthesised and tested as alternative substrates for the enzyme. Both compounds were found to be substrates for the DAH7P synthases from Escherichia coli, Pyrococcus furiosus and Mycobacterium tuberculosis, consistent with an acyclic mechanism for the enzyme for which neither C2 nor C3 hydroxyl groups are required for catalysis. The enzymes all showed greater tolerance for the loss of the C2 hydroxyl group than the C3 hydroxyl group. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.017
• 作为产物：
  描述：

  在 Dowex-H⁺ 作用下， 生成 (2-hydroxy-4-oxobutoxy)phosphonate
  参考文献：
  名称：

  Stereospecific deuteration of 2-deoxyerythrose 4-phosphate using 3-deoxy-D-arabino-heptulosonate 7-phosphate synthase

  摘要：

  Racemic 2-deoxyerythrose 4-phosphate was synthesized and one enantiomer of this compound was found to be a substrate for Escherichia coli 3 -deoxy-D -arabino-heptulosonate 7-phosphate synthase, the first enzyme of the shikimate pathway. When the reaction was carried out in deuterium oxide, an enzyme-catalyzed regio- and stereoselective incorporation of deuterium into the product was observed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.02.080

文献信息

• Investigating the role of the hydroxyl groups of substrate erythrose 4-phosphate in the reaction catalysed by the first enzyme of the shikimate pathway
  作者：David Tran、Amy L. Pietersma、Linley R. Schofield、Matthias Rost、Geoffrey B. Jameson、Emily J. Parker

  DOI：10.1016/j.bmcl.2011.09.017

  日期：2011.11

  3-Deoxy-D-arabino-heptulosonate 7-phosphate (DAH7P) synthase catalyses the first step of the shikimate pathway, which is responsible for the biosynthesis of aromatic amino acids in microorganisms and plants. This enzyme catalyses an aldol reaction between phosphoenolpyruvate and D-erythrose 4-phosphate to generate DAH7P. Both 2-deoxyerythrose 4-phosphate and 3-deoxyerythrose 4-phosphate were synthesised and tested as alternative substrates for the enzyme. Both compounds were found to be substrates for the DAH7P synthases from Escherichia coli, Pyrococcus furiosus and Mycobacterium tuberculosis, consistent with an acyclic mechanism for the enzyme for which neither C2 nor C3 hydroxyl groups are required for catalysis. The enzymes all showed greater tolerance for the loss of the C2 hydroxyl group than the C3 hydroxyl group. (C) 2011 Elsevier Ltd. All rights reserved.
• Stereospecific deuteration of 2-deoxyerythrose 4-phosphate using 3-deoxy-D-arabino-heptulosonate 7-phosphate synthase
  作者：Rachel M. Williamson、Amy L. Pietersma、Geoffrey B. Jameson、Emily J. Parker

  DOI：10.1016/j.bmcl.2005.02.080

  日期：2005.5

  Racemic 2-deoxyerythrose 4-phosphate was synthesized and one enantiomer of this compound was found to be a substrate for Escherichia coli 3 -deoxy-D -arabino-heptulosonate 7-phosphate synthase, the first enzyme of the shikimate pathway. When the reaction was carried out in deuterium oxide, an enzyme-catalyzed regio- and stereoselective incorporation of deuterium into the product was observed. (c) 2005 Elsevier Ltd. All rights reserved.