7-deaza-2'-deoxyadenosine 5'-monophosphate morpholidate triethylammonium salt

• 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: 7-deaza-2'-deoxyadenosine 5'-monophosphate morpholidate triethylammonium salt
• 英文别名: [(2R,3S,5R)-5-(4-aminopyrrolo[2,3-d]pyrimidin-7-yl)-3-hydroxyoxolan-2-yl]methoxy-morpholin-4-ylphosphinic acid;N,N-diethylethanamine
• 化学式: C₆H₁₅N*C₁₅H₂₂N₅O₆P
• 分子量: 500.535
• InChiKey: HYEJZDPUILKOOB-LUHWTZLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.46
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  148
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  7-deaza-2'-deoxyadenosine 5'-monophosphate morpholidate triethylammonium salt 、 β-烟酰胺单核苷酸 在 magnesium sulfate 、 formamide 、 manganese(ll) chloride 作用下， 反应 48.0h， 以60%的产率得到7-deaza-2'-deoxynicotinamide adenine dinucleotide triethylammonium salt
  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
• 作为产物：
  描述：

  吗啉 、 三乙胺 、 （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 、 2,2'-二硫二吡啶 、 三苯基膦 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以13%的产率得到7-deaza-2'-deoxyadenosine 3,'5'-bisphosphate morpholidate triethylammonium salt
  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.