[(R)-2-Acetoxy-3-(bis-benzyloxy-phosphoryloxy)-propane-1-sulfinyl]-acetic acid benzyl ester | 717920-90-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(R)-2-Acetoxy-3-(bis-benzyloxy-phosphoryloxy)-propane-1-sulfinyl]-acetic acid benzyl ester
• 英文别名: benzyl 2-[(2R)-2-acetyloxy-3-bis(phenylmethoxy)phosphoryloxypropyl]sulfinylacetate
• CAS: 717920-90-6
• 化学式: C₂₈H₃₁O₉PS
• 分子量: 574.589
• InChiKey: INPSHOYTICSHIX-WFZWBVOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  39
• 可旋转键数：
  18
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  134
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  [(R)-2-Acetoxy-3-(bis-benzyloxy-phosphoryloxy)-propane-1-sulfinyl]-acetic acid benzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 0.33h， 以99%的产率得到((R)-2-Acetoxy-3-phosphonooxy-propane-1-sulfinyl)-acetic acid
  参考文献：
  名称：

  Selective Inhibition of Trypanosoma brucei 6-Phosphogluconate Dehydrogenase by High-Energy Intermediate and Transition-State Analogues

  摘要：

  Two series of compounds were designed to mimic the transition state and high-energy intermediates (HEI) of the enzymatic reaction of 6-phosphogluconate dehydrogenase (6PGDH). Sulfoxide analogues (7-11) were designed to mimic the transition state during the oxidation of the substrate to 3-keto-6-phosphogluconate, an enzyme-bound intermediate of the enzyme. Hydroxamate and amide derivatives Of D-erythronic acid were designed to mimic the 1,2-cis-enediol HEI of the 6PGDH reaction. These two series of compounds were assayed as competitive inhibitors of the Trypanosoma brucei and sheep liver enzymes, and their selectivity value (ratio sheep/parasite) was calculated. The sulfoxide transition-state analogues showed weak and selective inhibition of the T. brucei enzyme. The hydroxamic derivatives showed potent and selective inhibition of the T brucei 6PGDH with a K-i in the nanomolar range.

  DOI：

  10.1021/jm031066i
• 作为产物：
  描述：

  ((R)-2,3-Dihydroxy-propylsulfanyl)-acetic acid benzyl ester 在 吡啶 、 4-二甲氨基吡啶 、 双氧水 作用下， 以 二氯甲烷 、 溶剂黄146 、 乙腈 为溶剂， 反应 25.5h， 生成 [(R)-2-Acetoxy-3-(bis-benzyloxy-phosphoryloxy)-propane-1-sulfinyl]-acetic acid benzyl ester
  参考文献：
  名称：

  Selective Inhibition of Trypanosoma brucei 6-Phosphogluconate Dehydrogenase by High-Energy Intermediate and Transition-State Analogues

  摘要：

  Two series of compounds were designed to mimic the transition state and high-energy intermediates (HEI) of the enzymatic reaction of 6-phosphogluconate dehydrogenase (6PGDH). Sulfoxide analogues (7-11) were designed to mimic the transition state during the oxidation of the substrate to 3-keto-6-phosphogluconate, an enzyme-bound intermediate of the enzyme. Hydroxamate and amide derivatives Of D-erythronic acid were designed to mimic the 1,2-cis-enediol HEI of the 6PGDH reaction. These two series of compounds were assayed as competitive inhibitors of the Trypanosoma brucei and sheep liver enzymes, and their selectivity value (ratio sheep/parasite) was calculated. The sulfoxide transition-state analogues showed weak and selective inhibition of the T. brucei enzyme. The hydroxamic derivatives showed potent and selective inhibition of the T brucei 6PGDH with a K-i in the nanomolar range.

  DOI：

  10.1021/jm031066i

文献信息

• Selective Inhibition of <i>Trypanosoma brucei</i> 6-Phosphogluconate Dehydrogenase by High-Energy Intermediate and Transition-State Analogues
  作者：Christophe Dardonville、Eliana Rinaldi、Michael P. Barrett、Reto Brun、Ian H. Gilbert、Stefania Hanau

  DOI：10.1021/jm031066i

  日期：2004.6.1

  Two series of compounds were designed to mimic the transition state and high-energy intermediates (HEI) of the enzymatic reaction of 6-phosphogluconate dehydrogenase (6PGDH). Sulfoxide analogues (7-11) were designed to mimic the transition state during the oxidation of the substrate to 3-keto-6-phosphogluconate, an enzyme-bound intermediate of the enzyme. Hydroxamate and amide derivatives Of D-erythronic acid were designed to mimic the 1,2-cis-enediol HEI of the 6PGDH reaction. These two series of compounds were assayed as competitive inhibitors of the Trypanosoma brucei and sheep liver enzymes, and their selectivity value (ratio sheep/parasite) was calculated. The sulfoxide transition-state analogues showed weak and selective inhibition of the T. brucei enzyme. The hydroxamic derivatives showed potent and selective inhibition of the T brucei 6PGDH with a K-i in the nanomolar range.