adenylyl-(2'->5')-adenylyl-(2'->5')-adenylyl-(2'->5')-adenosine | 73853-00-6

• 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: adenylyl-(2'->5')-adenylyl-(2'->5')-adenylyl-(2'->5')-adenosine
• 英文别名: A2'p5'A2'p5'A2'p5'A；Adenosine, adenylyl-(2'.5')-adenylyl-(2'.5')-adenylyl-(2'.5')-；[(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]methyl [(2R,3R,4R,5R)-2-(6-aminopurin-9-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate
• CAS: 73853-00-6
• 化学式: C₄₀H₄₉N₂₀O₂₂P₃
• 分子量: 1254.87
• InChiKey: NZNHTIWALNOMOW-HKIDEBSPSA-N

物化性质

• 密度：
  2.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -9.6
• 重原子数：
  85
• 可旋转键数：
  20
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  604
• 氢给体数：
  13
• 氢受体数：
  38

反应信息

• 作为产物：
  描述：

  5’-三磷酸腺苷 在 1,4-dithio-D,L-threitol 、 porcine oligoadenylate synthetase 1 、 magnesium chloride 、 calf alkaline phosphatase 作用下， 反应 3.0h， 生成 腺苷酰-(2'-5')-腺苷酰-(2'-5')腺苷 、 adenylyl-(2'->5')-adenylyl-(2'->5')-adenylyl-(2'->5')-adenosine 、 adenylyl-2',5'-adenosine
  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

文献信息

• Natural Occurrence of 2′,5′-Linked Heteronucleotides in Marine Sponges
  作者：Annika Lopp、Tönu Reintamm、Anne Kuusksalu、Indrek Tammiste、Arno Pihlak、Merike Kelve

  DOI：10.3390/md8020235

  日期：——

  muricata and Chondrilla nucula are able to catalyze in vivo synthesis of 2-5A as well as the synthesis of a series 2',5'-linked heteronucleotides which accompanied high levels of 2',5'-diadenylates. In dephosphorylated perchloric acid extracts of the sponges, these heteronucleotides were identified as A2'p5'G, A2' p5'U, A2'p5'C, G2'p5'A and G2' p5'U. The natural occurrence of 2'-adenylated NAD(+) was also

  2',5'-寡聚腺苷酸合成酶 (OAS) 作为哺乳动物干扰素诱导的抗病毒酶系统的组成部分，催化细胞 ATP 寡聚化为 2',5'-连接的寡聚腺苷酸 (2-5A)。尽管脊椎动物 OAS 在体外条件下已被表征为 2'-核苷酸转移酶，但从未证明 2-5A 以外的 2',5'-寡核苷酸的自然存在。在这里，我们已经证明来自海洋海绵 Thenea muricata 和 Chondrilla nucula 的 OAS 能够催化 2-5A 的体内合成以及一系列 2',5' 连接的杂核苷酸的合成，这些杂核苷酸伴随着高水平的 2'， 5'-二腺苷酸。在海绵的去磷酸化高氯酸提取物中，这些异核苷酸被鉴定为 A2'p5'G、A2'p5'U、A2' p5'C、G2'p5'A 和 G2'p5'U。还检测到 2'-腺苷酸化 NAD(+) 的自然发生。体外试验表明，除了 ATP 外，GTP 还是海绵 OAS 的良好底物，尤其是来自
• 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.