pA^3'pA^3'pA | 1684-34-0

• 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: pA^3'pA^3'pA
• 英文别名: r(pA)₃；Triadenylsaeure；5'-O-Phosphoryl-adenosyl-(3'->5')-adenosyl-(3'->5')-adenosin；adenylyl-(5'->3')-adenylyl-(5'->3')-[5']adenylic acid；P-rAdo-P-rAdo-P-rAdo；[(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-(phosphonooxymethyl)oxolan-3-yl] hydrogen phosphate
• CAS: 1684-34-0
• 化学式: C₃₀H₃₈N₁₅O₁₉P₃
• 分子量: 1005.64
• InChiKey: MUSCXRZQUILYGM-UQTMIEBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -8.7
• 重原子数：
  67
• 可旋转键数：
  16
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  496
• 氢给体数：
  11
• 氢受体数：
  31

反应信息

• 作为产物：
  描述：

  adenosine 5'-phosphorimidazolide 、 5'-phosphoadenylyl-(3'->5')-adenosine 在 sodium chloride 、 magnesium chloride 、 4-羟乙基哌嗪乙磺酸 作用下， 生成 pA^3'pA^3'pA
  参考文献：
  名称：

  Kinetic and Mechanistic Analysis of Dinucleotide and Oligonucleotide Formation from the 5'-Phosphorimidazolide of Adenosine on Na+-Montmorillonite

  摘要：

  The rate constants for the condensation reaction of the 5'-phosphorimidazolide of adenosine (ImpA) to form dinucleotides and oligonucleotides have been measured in the presence of Na+-volclay (a Na+-montmorillonite) in pH 8 aqueous solution at 25 degrees C. The rates of the reaction of ImpA with an excess of adenosine 5'-monophosphoramidate (NH(2)pA), P-1,P-2-diadenosine 5',5'-pyrophosphate (A(5') ppA), or adenosine 5'-monophosphate (5'-AMP or pA) in the presence of the montmorillonite to form NH(2)pA(3') pA, A(5') ppA3' pA, and pA(3') pA, respectively, were measured. Only 3'5'-linked products ware observed. The magnitude of the rate constants decrease in the order NH(2)pA(3') pA > A(5')-ppA(3') pA > pA(3') pA. The binding of ImpA to montmorillonite was measured, and the adsorption isotherm was determined. The binding of ImpA to montmorillonite and the formation of higher oligonucleotides is not observed in the absence of salts. Mg2(+) enhances binding and oligonucleotide formation more than Ca2+ and Na+. The rate constants for the oligonucleotide formation were determined from the reaction products formed from 10 to 40 mM ImpA in the presence of Na+-montmorillonite using the computer program SIMFIT. The magnitudes of the rate constants for the formation of oligonucleotides increased in the order 2-mer < 3-mer < 4-mer ... 7-mer. The rate constants for dinucleotide and trinucleotide formation are more than 1000 times larger than those measured in the absence of montmorillonite. The rate constants for the formation of dinucleotide, trinucleotide, and tetranucleotide are 41, 2.6, and 3.7 times larger than those for the formation of oligo(G)s with a poly (C) template. The hydrolysis of ImpA was accelerated 35 times in the presence of the montmorillonite. The catalytic ability of montmorillonite to form dinucleotides and oligonucleotides is quantitatively evaluated and possible pathways for oligo(A) formation are proposed.

  DOI：

  10.1021/ja00096a013

文献信息

• Montmorillonite catalysis of RNA oligomer formation in aqueous solution. A model for the prebiotic formation of RNA
  作者：James P. Ferris、Gozen Ertem

  DOI：10.1021/ja00079a006

  日期：1993.12

  are almost ineffective catalysts. 2',5'-Linked oligomers, up to the tetramer in length, are formed using UO2(2+)-montmorillonite. The structure analysis of individual oligomer fractions was performed by selective enzymatic and KOH hydrolytic studies followed by HPLC analysis of the reaction products. It is concluded from the composition of the oligomers that the rate of addition ImpA to a 3'-terminus

  在室温下，在 Na(+)-蒙脱石存在下，腺苷磷咪唑化物 (ImpA) 在 pH 8 的水溶液中反应，形成长达 11 聚体的腺苷酸低聚物。这些低聚物通过磷酸二酯键连接，其中 3',5'-键以 2:1 的比例超过 2',5'-键。ImpA、A5'ppA 的 9:1 混合物的反应导致形成具有 3:1 比例的 3',5'-与 2',5'-连接的磷酸二酯键的低聚物。这些低聚物中有很大一部分包含 A5'ppA 组。A5'ppA 与 ImpA 的反应比 5'-ADP (ppA) 或 5'-ATP (pppA) 快得多。与蒙脱石相关的可交换阳离子影响观察到的 Li+、Na+、NH4+、Ca2+ 是更有效的，而 Mg2+ 和 Al3+ 几乎是无效的催化剂。使用 UO2(2+)-蒙脱石形成 2',5'-连接的低聚物，直至四聚体的长度。通过选择性酶促和 KOH 水解研究，然后对反应产物进行 HPLC 分析，对各
• Kinetic and Mechanistic Analysis of Dinucleotide and Oligonucleotide Formation from the 5'-Phosphorimidazolide of Adenosine on Na+-Montmorillonite
  作者：Kunio Kawamura、James P. Ferris

  DOI：10.1021/ja00096a013

  日期：1994.8

  The rate constants for the condensation reaction of the 5'-phosphorimidazolide of adenosine (ImpA) to form dinucleotides and oligonucleotides have been measured in the presence of Na+-volclay (a Na+-montmorillonite) in pH 8 aqueous solution at 25 degrees C. The rates of the reaction of ImpA with an excess of adenosine 5'-monophosphoramidate (NH(2)pA), P-1,P-2-diadenosine 5',5'-pyrophosphate (A(5') ppA), or adenosine 5'-monophosphate (5'-AMP or pA) in the presence of the montmorillonite to form NH(2)pA(3') pA, A(5') ppA3' pA, and pA(3') pA, respectively, were measured. Only 3'5'-linked products ware observed. The magnitude of the rate constants decrease in the order NH(2)pA(3') pA > A(5')-ppA(3') pA > pA(3') pA. The binding of ImpA to montmorillonite was measured, and the adsorption isotherm was determined. The binding of ImpA to montmorillonite and the formation of higher oligonucleotides is not observed in the absence of salts. Mg2(+) enhances binding and oligonucleotide formation more than Ca2+ and Na+. The rate constants for the oligonucleotide formation were determined from the reaction products formed from 10 to 40 mM ImpA in the presence of Na+-montmorillonite using the computer program SIMFIT. The magnitudes of the rate constants for the formation of oligonucleotides increased in the order 2-mer < 3-mer < 4-mer ... 7-mer. The rate constants for dinucleotide and trinucleotide formation are more than 1000 times larger than those measured in the absence of montmorillonite. The rate constants for the formation of dinucleotide, trinucleotide, and tetranucleotide are 41, 2.6, and 3.7 times larger than those for the formation of oligo(G)s with a poly (C) template. The hydrolysis of ImpA was accelerated 35 times in the presence of the montmorillonite. The catalytic ability of montmorillonite to form dinucleotides and oligonucleotides is quantitatively evaluated and possible pathways for oligo(A) formation are proposed.