Adenosyl-<3'-5'>-adenosyl-<3'-5'>-adenosin | 917-44-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: Adenosyl-<3'-5'>-adenosyl-<3'-5'>-adenosin
• 英文别名: adenylyl-(3'->5')-adenylyl-(3'->5')-adenosine；ApApA；Adenylyl-(5'->3')-adenylyl-(5'->3')-adenosine；[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3-[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-4-hydroxyoxolan-2-yl]methyl [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate
• CAS: 917-44-2
• 化学式: C₃₀H₃₇N₁₅O₁₆P₂
• 分子量: 925.662
• InChiKey: CUJKPTPMTCNOKC-UQTMIEBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -7.6
• 重原子数：
  63
• 可旋转键数：
  14
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  449
• 氢给体数：
  10
• 氢受体数：
  28

反应信息

• 作为反应物：
  描述：

  Adenosyl-<3'-5'>-adenosyl-<3'-5'>-adenosin 在 ribonuclease T₂ 作用下， 以 水 为溶剂， 反应 1.0h， 生成 5'-腺嘌呤核苷酸 、 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：

  N⁶-Benzoyladenosyl-<3'-5'>-N⁶-benzoyladenosyl-<3'-5'>-N⁶-benzoyladenosin 在 氨 作用下， 以 水 为溶剂， 反应 24.0h， 生成 Adenosyl-<3'-5'>-adenosyl-<3'-5'>-adenosin
  参考文献：
  名称：

  核苷酸，XVII。合成von homogenen Adenosyl-3'，5'-Oligomeren nach dem Phosphotriester-Verfahren † ‡

  摘要：

  核苷酸，十七。磷酸三酯法合成均相腺苷3'，5'-低聚物

  DOI：

  10.1002/hlca.19830660713

文献信息

• ARTIFICIAL NUCLEIC ACID MOLECULES FOR IMPROVED PROTEIN OR PEPTIDE EXPRESSION
  申请人：CureVac GmbH

  公开号：US20150218554A1

  公开（公告）日：2015-08-06

  The invention relates to an artificial nucleic acid molecule comprising at least one 5′UTR element which is derived from a TOP gene, at least one open reading frame, and preferably at least one histone stem-loop. Optionally the artificial nucleic acid molecule may further comprise, e.g. a poly(A)sequence, a poyladenylation signal, and/or a 3′UTR. The invention further relates to the use of such an artificial nucleic acid molecule in gene therapy and/or genetic vaccination.

  本发明涉及一种人造核酸分子，该分子包括至少一个来自TOP基因的5'UTR元素，至少一个开放阅读框架，以及最好至少一个组蛋白茎环。可选地，该人造核酸分子还可以包括例如一个poly(A)序列，一个polyadenylation信号和/或一个3'UTR。本发明还涉及在基因治疗和/或基因疫苗中使用这种人造核酸分子的用途。
• Synthesis and structural characterization of diastereomeric isomers of RNA trimer adenylyl(3′-5′)adenylyl(3′-5′)adenosine
  作者：Hidehito Urata、Hisafumi Hara、Yoshihiro Hirata、Norihiko Ohmoto、Masao Akagi

  DOI：10.1016/j.tetasy.2005.07.026

  日期：2005.9

  We have synthesized the diastereomeric isomers of adenylyl(3'-5')adenylyl(3'-5')adenosine (ApApA), and investigated their helical structures and hybridization properties with D-poly(U) by circular dichroism (CD) and UV melting experiments. The configuration of the 5'-end residue of ApApA has little effect on the helical structure. The configuration of the 3'-end residue has little effect on the stability of the triplex, and the chiral modifications cause complicated effects on the helical structure of ApApA and its triplex-forming ability with D-poly(U), depending on the site of the modification. (c) 2005 Elsevier Ltd. All rights reserved.
• On the mechanism of T4 RNA ligase
  作者：F. R. Bryant、S. J. Benkovic

  DOI：10.1021/ja00393a047

  日期：1981.2
• US20140273036A1
  申请人：——

  公开号：——

  公开（公告）日：——
• Nucleotide, XVII. Synthese von homogenen Adenosyl-3?,5?-Oligomeren nach dem Phosphotriester-Verfahren
  作者：Dieter Flockerzi、Eugen Uhlmann、Wolfgang Pfleiderer

  DOI：10.1002/hlca.19830660713

  日期：1983.11.2

  Nucleotides, XVII. Synthesis of Homogeneous Adenosyl-3′,5′-oligomers by the Phosphotriester Method

  核苷酸，十七。磷酸三酯法合成均相腺苷3'，5'-低聚物