monosodium mono((2R,3aR,7R,7aS)-2-methyl-7-(phosphonatooxy)-3a,4,7,7a-tetrahydrobenzo[d][1,3]dioxole-2,5-dicarboxylate) | 135414-91-4

• 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: monosodium mono((2R,3aR,7R,7aS)-2-methyl-7-(phosphonatooxy)-3a,4,7,7a-tetrahydrobenzo[d][1,3]dioxole-2,5-dicarboxylate)
• CAS: 135414-91-4
• 化学式: C₁₀H₉O₁₀P*4Na
• 分子量: 412.108
• InChiKey: DHHVKIPXBOPZID-NDGFODGGSA-J

计算性质

• 辛醇/水分配系数(LogP)：
  -7.47
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  171.14
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  (-)-5-enolpyruvylshikimate 3-phosphate, tetrasodium salt 在 5-enolpyruvoylshikimate 3-phosphate synthase 作用下， 以 水 为溶剂， 反应 240.0h， 以1.1 g的产率得到monosodium mono((2R,3aR,7R,7aS)-2-methyl-7-(phosphonatooxy)-3a,4,7,7a-tetrahydrobenzo[d][1,3]dioxole-2,5-dicarboxylate)
  参考文献：
  名称：

  Novel product from EPSP (5-enolpyruvoylshikimate 3-phosphate) synthase at equilibrium

  摘要：

  DOI：

  10.1021/ja00160a068

文献信息

• Solution conformations of two shikimate 3-phosphates: determination by NMR and molecular mechanics calculations
  作者：Stephen Castellino、Gregory C. Leo、R. Douglas Sammons、James A. Sikorski

  DOI：10.1021/jo00017a034

  日期：1991.8

  The solution conformation of two substituted cyclohexenes: shikimate 3-phosphate (S3P), 1, and a conformationally constrained derivative, the pyruvoyl ketal of 4,5-shikimate 3-phosphate (EPSP ketal),1 2, have been determined by a combination of NMR and molecular mechanics methods. The solution conformations were examined by 3J(HH) coupling constant analysis, quantified NOE experiments, and molecular mechanics calculatins. The preferred conformation of S3P in the pH range 5-9, which brackets the second ionization of the phosphate group, is best described as a half-chair in which the phosphate group occupies an axial position. The proton-proton coupling constants suggest dihedral angle averaging in the ring. Populations of the alternative half-chair with the phosphate group in the equatorial position or twist-boat conformations are not observed. The experimental conformation of the EPSP ketal, a bicyclic analogue, was also determined by coupling constant analysis and NOE measurements. The EPSP ketal retains the half-chain conformation with the axial phosphate. The experimentally derived conformation of 2 reveals less deviation from the energy-minimized structure than was observed for S3P due to the rigid nature of this bicyclic system.