Phosphoric acid mono-((2R,5S)-5-hydroxymethyl-tetrahydro-furan-2-yl) ester | 775276-11-4

• 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: Phosphoric acid mono-((2R,5S)-5-hydroxymethyl-tetrahydro-furan-2-yl) ester
• 英文别名: (2R,5S)-5-(Hydroxymethyl)oxolan-2-yl dihydrogen phosphate；[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl] dihydrogen phosphate
• CAS: 775276-11-4
• 化学式: C₅H₁₁O₆P
• 分子量: 198.112
• InChiKey: XYWDMVGRKLPPRF-CRCLSJGQSA-N

物化性质

• 沸点：
  427.9±55.0 °C(Predicted)
• 密度：
  1.57±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  96.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2',3'-二脱氧胸苷 在 recombinant Escherichia coli thymidine phosphorylase 作用下， 生成 胸腺嘧啶 、 Phosphoric acid mono-((2R,5S)-5-hydroxymethyl-tetrahydro-furan-2-yl) ester
  参考文献：
  名称：

  Substrate Specificity of Thymidine Phosphorylase ofE. Coli: Role of Hydroxyl Groups

  摘要：

  Substrate specificity of E. coli thymidine phosphorylase to pyrimidine nucleoside modified at 5 '-, 3 '-, and 2 '-positions of sugar moiety has been studied. Equilibrium (Keq) and kinetics constants of phosphorolysis reaction of nucleosides were measured. The most important hydrogen bonds in enzyme-substrate complex have been determined.

  DOI：

  10.1080/15257770802257895

文献信息

• Gene Therapy of Cancer: Activation of Nucleoside Prodrugs with<i>E. coli</i>Purine Nucleoside Phosphorylase
  作者：John A. Secrist、William B. Parker、Paula W. Allan、L. Lee Bennett、William R. Waud、Jackie W. Truss、Anita T. Fowler、John A. Montgomery、Steven E. Ealick、Alan H. Wells、G. Yancey Gillespie、V. K. Gadi、Eric J. Sorscher

  DOI：10.1080/15257779908041562

  日期：1999.4

  During the last few years, many gene therapy strategies have been developed for various disease targets. The development of anticancer gene therapy strategies to selectively generate cytotoxic nucleoside or nucleotide analogs is an attractive goal. One such approach involves the delivery of herpes simplex virus thymidine kinase followed by the acyclic nucleoside analog ganciclovir. We have developed another gene therapy methodology for the treatment of cancer that has several significant attributes. Specifically, our approach involves the delivery off. coli purine nucleoside phosphorylase, followed by treatment with a relatively non-toxic nucleoside prodrug that is cleaved by the enzyme to a toxic compound. This presentation describes the concept, details our search for suitable prodrugs, and summarizes the current biological data.
• Substrate Specificity of Thymidine Phosphorylase of<i>E. Coli</i>: Role of Hydroxyl Groups
  作者：Natalya G. Panova、Cyril S. Alexeev、Konstantin M. Polyakov、Sergei A. Gavryushov、Anatoliy M. Kritzyn、Sergey N. Mikhailov

  DOI：10.1080/15257770802257895

  日期：2008.11.13

  Substrate specificity of E. coli thymidine phosphorylase to pyrimidine nucleoside modified at 5 '-, 3 '-, and 2 '-positions of sugar moiety has been studied. Equilibrium (Keq) and kinetics constants of phosphorolysis reaction of nucleosides were measured. The most important hydrogen bonds in enzyme-substrate complex have been determined.