[(2R,3S,5R)-5-(4-aminopyrrolo[2,3-d]pyrimidin-7-yl)-2-(phosphonooxymethyl)oxolan-3-yl] dihydrogen phosphate | 1011457-99-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并嘧啶类
• 英文名称: [(2R,3S,5R)-5-(4-aminopyrrolo[2,3-d]pyrimidin-7-yl)-2-(phosphonooxymethyl)oxolan-3-yl] dihydrogen phosphate
• CAS: 1011457-99-0
• 化学式: C₁₁H₁₆N₄O₉P₂
• 分子量: 410.217
• InChiKey: UGOOGKFIRSIAKI-DJLDLDEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.1
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  200
• 氢给体数：
  5
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  （2R，3S，5R）-5-（4-氨基-7H-吡咯[2,3-D]嘧啶-7-基-2 -（羟甲基）四氢呋喃-3-醇 在 磷酸三乙酯 、 三氯氧磷 作用下， 反应 2.0h， 生成 7-deaza-2’-deoxyadenosine-5’-O-monophosphate 、 [(2R,3S,5R)-5-(4-aminopyrrolo[2,3-d]pyrimidin-7-yl)-2-(phosphonooxymethyl)oxolan-3-yl] dihydrogen phosphate
  参考文献：
  名称：

  Chemoenzymatic Synthesis of 7-Deaza Cyclic Adenosine 5‘-Diphosphate Ribose Analogues, Membrane-Permeant Modulators of Intracellular Calcium Release

  摘要：

  [Graphics]An optimized synthetic route to 7-deaza-8-bromo-cyclic adenosine 5'-diphosphate ribose (7-deaza-8-bromo-cADPR 3), an established cell-permeant, hydrolysis-resistant cyclic adenosine 5'-diphosphate ribose (cADPR) antagonist, is presented. Using NMR analysis, we found that 3 adopted a C-2'endo conformation in the N9-linked ribose and a syn conformation about the N9-glycosyl linkage, which are similar to that of cADPR. The synthetic route was also employed to produce 7-deaza-2'-deoxy-cADPR 4, a potential cell-permeant cADPR analogue. 3 and 4 were more stable to chemical hydrolysis, consistent with the observation that 7-deaza-cADPR analogues are more stable than their parent adenosine derivatives. 3 was also found to be stable to enzyme-mediated hydrolysis using CD38 ectoenzyme.

  DOI：

  10.1021/jo071236p

文献信息

• Chemoenzymatic Synthesis of 7-Deaza Cyclic Adenosine 5‘-Diphosphate Ribose Analogues, Membrane-Permeant Modulators of Intracellular Calcium Release
  作者：Bo Zhang、Victoria C. Bailey、Barry V. L. Potter

  DOI：10.1021/jo071236p

  日期：2008.3.1

  [Graphics]An optimized synthetic route to 7-deaza-8-bromo-cyclic adenosine 5'-diphosphate ribose (7-deaza-8-bromo-cADPR 3), an established cell-permeant, hydrolysis-resistant cyclic adenosine 5'-diphosphate ribose (cADPR) antagonist, is presented. Using NMR analysis, we found that 3 adopted a C-2'endo conformation in the N9-linked ribose and a syn conformation about the N9-glycosyl linkage, which are similar to that of cADPR. The synthetic route was also employed to produce 7-deaza-2'-deoxy-cADPR 4, a potential cell-permeant cADPR analogue. 3 and 4 were more stable to chemical hydrolysis, consistent with the observation that 7-deaza-cADPR analogues are more stable than their parent adenosine derivatives. 3 was also found to be stable to enzyme-mediated hydrolysis using CD38 ectoenzyme.