5'-O-triphosphoadenylyl-(2'->5')-adenosine | 65954-94-1

• 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')-adenosine
• 英文别名: pppA2'p5'A；[[(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] phosphono hydrogen phosphate
• CAS: 65954-94-1
• 化学式: C₂₀H₂₈N₁₀O₁₉P₄
• 分子量: 836.393
• InChiKey: YHHSPPDBQDMAPZ-XPWFQUROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -8.3
• 重原子数：
  53
• 可旋转键数：
  14
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  434
• 氢给体数：
  10
• 氢受体数：
  27

反应信息

• 作为产物：
  描述：

  Phosphoric acid (2R,3R)-3-(6-amino-purin-9-yl)-2,3-dihydroxy-propyl ester (2R,3R,4R,5R)-2-(6-amino-purin-9-yl)-4-hydroxy-5-phosphonooxymethyl-tetrahydro-furan-3-yl ester 在 三辛胺 、 三丁基焦磷酸铵 、 三乙胺 、 N,N'-羰基二咪唑 作用下， 生成 5'-O-triphosphoadenylyl-(2'->5')-adenosine
  参考文献：
  名称：

  Bis(2,2,2-trichloroethyl) phosphorochloridite as a reagent for the phosphorylation of oligonucleotides: preparation of 5'-phosphorylated 2',5'-oligoadenylates

  摘要：

  DOI：

  10.1021/jo00333a016

文献信息

• High yield synthesis, purification and characterisation of the RNase L activators 5′-triphosphate 2′–5′-oligoadenylates
  作者：B. Morin、N. Rabah、J. Boretto-Soler、H. Tolou、K. Alvarez、B. Canard

  DOI：10.1016/j.antiviral.2010.06.003

  日期：2010.9

  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.
• 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