2-deoxy-D-erythrose 4-phosphate

• 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-deoxy-D-erythrose 4-phosphate
• 英文别名: phosphoric acid mono-((S)-2-hydroxy-4-oxo-butyl) ester；O⁴-phosphono-D-2-deoxy-tetrose；[(2S)-2-hydroxy-4-oxobutyl] dihydrogen phosphate
• 化学式: C₄H₉O₆P
• 分子量: 184.086
• InChiKey: LQIRHIGPILJQHV-BYPYZUCNSA-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-deoxy-D-erythrose 4-phosphate 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
  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：

  (S)-3-(5,5-dimethyl-1,3-dioxan-2-yl)-2-hydroxypropyl phosphate 在 Dowex(R) 50W-H(+) 、 水 作用下， 生成 2-deoxy-D-erythrose 4-phosphate
  参考文献：
  名称：

  两种密切相关的醛糖样酶催化反应的机理差异。

  摘要：

  苏糖4-磷酸和2-脱氧赤藓酸4-磷酸与3-脱氧-D-阿拉伯糖庚酸7磷酸合酶（DAH7PS）的相互作用的分析揭示了DAH7PS催化的反应与之前由DHA7PS催化的反应之间先前未发现的机理差异。紧密相关的酶，3-脱氧-D-甘露聚糖-八磺酸盐8-磷酸合酶（KDO8PS）。

  DOI：

  10.1039/b511661a

文献信息

• Phosphorylated sugars. Part XII. An unexpected phosphate-group migration during the attempted preparation of 2-deoxy-d-erythro-pentose 5-(dihydrogen phosphate) from glucometasaccharinic acid 6-phosphate
  作者：F. Trigalo、Patricia Szabó、L. Szabó

  DOI：10.1039/j39680000901

  日期：——

  The phosphorylated 2-deoxy-D-erythro-pentose previously obtained by Ruff degradation of glucometasaccharinic acid 6-phosphate is shown to be a 4 : 1 mixture of the 4- and 5-phosphates of the deoxy-pentose; the 3-phosphate is absent. Methods are described for the electrophoretic separation of the phosphate esters fromed when 2-deoxy-D-erythro-pentose 3-, 4-, and 5-phosphates are successively treated

  磷酸化的2-脱氧d -赤-pentose先前由glucometasaccharinic酸-6-磷酸拉夫降解得到被示出为一个4：脱氧戊糖的4-和5-磷酸酯的1:1的混合物; 不存在3-磷酸酯。描述了将2-脱氧-D-赤-戊糖3-，4-和5-磷酸依次用高碘酸盐和硼氢化物处理后，从中分离磷酸酯的方法。通过glucometasaccharinic酸5-磷酸用高碘2-脱氧的持久氧化d -赤获得了4-磷酸戊糖-磷酸酯。在Dische的二苯胺测试的标准条件下，与5-磷酸酯相比，该酯仅产生游离脱氧-戊糖给出的颜色的60％。