5'-O-triphosphoadenylyl-(2'->5')-adenylyl-(2'->5')-adenosine | 65954-93-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷酸
• 英文名称: 5'-O-triphosphoadenylyl-(2'->5')-adenylyl-(2'->5')-adenosine
• 英文别名: 5'-Triphosphoadenylyl(2'-5')adenylyl(2'-5')adenosine；5'-triphosphate of 2',5'-triadenylate；ppp5'A2'p5'A2'p5'A；pppA2'p5'A2'p5'A；adenylyl-(5'->2')-adenylyl-(5'->2')-O^5'-tetrahydroxy[1]triphosphoryl-adenosine；[[(2r,3r,4r,5r)-5-(6-Aminopurin-9-Yl)-4-[[(2r,3r,4r,5r)-5-(6-Aminopurin-9-Yl)-4-[[(2r,3s,4r,5r)-5-(6-Aminopurin-9-Yl)-3,4-Dihydroxy-Oxolan-2-Yl]methoxy-Hydroxy-Phosphoryl]oxy-3-Hydroxy-Oxolan-2-Yl]methoxy-Hydroxy-Phosphoryl]oxy-3-Hydroxy-Oxolan-2-Yl]methoxy-Hydroxy-Phosphoryl] Phosphono Hydrogen Phosphate；[[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-4-[[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-4-[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate
• CAS: 65954-93-0
• 化学式: C₃₀H₄₀N₁₅O₂₅P₅
• 分子量: 1165.6
• InChiKey: RTAGLZBJCCVJET-UQTMIEBXSA-N

物化性质

• 密度：
  2.61±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -10.9
• 重原子数：
  75
• 可旋转键数：
  20
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  589
• 氢给体数：
  13
• 氢受体数：
  37

反应信息

• 作为反应物：
  描述：

  5'-O-triphosphoadenylyl-(2'->5')-adenylyl-(2'->5')-adenosine 在 calf alkaline phosphatase 作用下， 以 水 为溶剂， 生成 腺苷酰-(2'-5')-腺苷酰-(2'-5')腺苷
  参考文献：
  名称：

  High yield synthesis, purification and characterisation of the RNase L activators 5′-triphosphate 2′–5′-oligoadenylates

  摘要：

  Upon viral infection, double-stranded viral RNA is detected very early in the host cell by several cellular 2'-5' oligoadenylate synthetases, which synthesize 2'-5' adenylate oligonucleotides that activate the cellular RNase L, firing an early primary antiviral response through self and non-self RNA cleavage. Transfecting cells with synthetic 2'-5' adenylate oligonucleotides activate RNase L, and thus provide a useful shortcut to study the early steps of cellular and viral commitments into this pathway. Defined 2'-5' adenylate oligonucleotides can be produced in vitro, but their controlled synthesis, purification, and characterisation have not been reported in detail. Here, we report a method suitable to produce large amounts of 2-5As of defined lengths in vitro using porcine OAS1 (pOAS) and human OAS2 (hOAS). We have synthesized a broad spectrum of 2-5As at the milligram scale and report an HPLC-purification and characterisation protocol with quantified yield for 2-5A of various lengths. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.antiviral.2010.06.003
• 作为产物：
  描述：

  腺苷酰-(2'-5')-腺苷酰-(2'-5')腺苷 在 磷酸三甲酯 、 三正丁胺 、 三丁基焦磷酸铵 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 5'-O-triphosphoadenylyl-(2'->5')-adenylyl-(2'->5')-adenosine
  参考文献：
  名称：

  2-5A的3'-氟-3'-脱氧类似物的立体化学在与小鼠RNase L结合和激活中的作用

  摘要：

  两套2-5A类似物的三聚体的含9-（3-氟-3-脱氧β-d木-呋喃糖基）腺嘌呤（A合成˚F）或3'-氟-3'-脱氧腺苷（A ˚F）描述了在链的不同位置上的）以及相应的5'-单磷酸盐和5'-二磷酸化（核心）三聚体的制备。2-5A（i）的每个核糖和木糖异构体对的氟脱氧类似物与p 3（A2'p）3 A3'[ 32 P] pC3'p竞争结合L 929细胞提取物中RNase L的能力，和（ii）从L 929激活部分纯化的RNase L将用于水解聚（U）[ 3 H]的细胞提取物与相关的3'-脱氧类似物[ Torrence等人，J。化学 263，1131（1988）]和三聚体母体，第3阿3，分别使用radiobinding和RNase L-（2'，5'）pentaadenylate（芯） -琼脂糖测定，。证据表明三聚体的立体化学起着重要作用，特别是在第二步过程中。最惊人的发现是，与2-5A相比，p 3 A（A

  DOI：

  10.1002/recl.19951140202

文献信息

• Mg(II) ion-mediated conversion of mono- and oligonucleotides to 5′-polyphosphates in aqueous solution
  作者：Hiroaki Sawai、Yoshiko Inaba、Atsushi Hirano、Hiromichi Wakai、Masamitsu Shimazu

  DOI：10.1016/s0040-4039(00)74092-5

  日期：1993.7

  5′-Polyphosphates of mono- and oligonucleotides were prepared from the corresponding 5′-monophosphates with phosphorotriimidazolide or phosphorotribenzimidazolide mediated by Mg(II) or Mn(II) ion in aqueous solution.

  由相应的5'-单磷酸与Mg（II）或Mn（II）离子介导的磷酸三亚咪唑化物或磷酸三苯并咪唑啉化物在水溶液中制备单-和寡核苷酸的5'-多磷酸。
• Bis(2,2,2-trichloroethyl) phosphorochloridite as a reagent for the phosphorylation of oligonucleotides: preparation of 5'-phosphorylated 2',5'-oligoadenylates
  作者：Jiro Imai、Paul F. Torrence

  DOI：10.1021/jo00333a016

  日期：1981.9
• Chemical synthesis of pppA2'p5'A2'p5'A, an interferon-induced inhibitor of protein synthesis, and some functional analogs
  作者：Jack A. J. Den Hartog、Robert A. Wijnands、Jacques H. Van Boom、Roberto Crea

  DOI：10.1021/jo00324a010

  日期：1981.5
• Synthesis of pppA2′p5′A2′p5′A γ-amidates by one pot procedure from A2′p5′A2′p5′A
  作者：Ágnes Nyilas

  DOI：10.1016/s0040-4039(97)00351-1

  日期：1997.4

  One pot synthesis of gamma-amidate of pppA2'p5'A2'p5'A described here using phosphoroxychloride and bis-tri-n-butylammonium pyrophosphate for preparing cyclic trimetaphosphate intermediate opening up with n-decylamin. (C) 1997 Elsevier Science Ltd.
• Expedient chemical synthesis of sequence-specific 2',5'-oligonucleotides
  作者：Jiro Imai、Paul F. Torrence

  DOI：10.1021/jo00209a014

  日期：1985.5