[5-(2-氨基-6-氧代-3H-嘌呤-9-基)-3,4-二羟基四氢呋喃-2-基]甲基[5-(6-氨基嘌呤-9-基)-4-羟基-2-(羟基甲基)四氢呋喃-3-基]磷酸氢酯 | 3352-23-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - （3'->5'）-二核苷酸和类似物
• 中文名称: [5-(2-氨基-6-氧代-3H-嘌呤-9-基)-3,4-二羟基四氢呋喃-2-基]甲基[5-(6-氨基嘌呤-9-基)-4-羟基-2-(羟基甲基)四氢呋喃-3-基]磷酸氢酯
• 英文名称: ApG
• 英文别名: Adenylyl-(3'->5')-guanosine；[(2R,3S,4R,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate
• CAS: 3352-23-6
• 化学式: C₂₀H₂₅N₁₀O₁₁P
• 分子量: 612.453
• InChiKey: LWBLDUTUVIXFJE-INFSMZHSSA-N

物化性质

• 密度：
  2.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -5.8
• 重原子数：
  42
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  310
• 氢给体数：
  8
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  [5-(2-氨基-6-氧代-3H-嘌呤-9-基)-3,4-二羟基四氢呋喃-2-基]甲基[5-(6-氨基嘌呤-9-基)-4-羟基-2-(羟基甲基)四氢呋喃-3-基]磷酸氢酯 在 TlOH radical cation 作用下， 生成 ApG deprotonated radical cation
  参考文献：
  名称：

  Electron transfer in di(deoxy)nucleoside phosphates in aqueous solution: rapid migration of oxidative damage (via adenine) to guanine

  摘要：

  In aqueous solution, the one-electron loss centers created statistically by the oxidant SO4.- or by photoionization in di(2'-deoxy)nucleoside phosphates (DNPs) containing the base guanine (G) become localized at G, as concluded from pulse radiolysis and 193-nm laser photolysis experiments. From the latter it is evident that, in the case of adenylyl(3'-->5')guanosine (ApG), the charge-transfer process is complete in less-than-or-equal-to 50 ns. With DNPs containing a pyrimidine and the purine base adenine, the oxidative damage is collected by the adenine moiety (k greater-than-or-equal-to 2 X 10(5) s-1).

  DOI：

  10.1021/ja00059a044
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 bismuth Hydroxide 、 水 作用下， 生成 [5-(2-氨基-6-氧代-3H-嘌呤-9-基)-3,4-二羟基四氢呋喃-2-基]甲基[5-(6-氨基嘌呤-9-基)-4-羟基-2-(羟基甲基)四氢呋喃-3-基]磷酸氢酯
  参考文献：
  名称：

  Dimroth; Witzel, Justus Liebigs Annalen der Chemie, 1959, vol. 620, p. 109,110,116,118

  摘要：

  DOI：

文献信息

• Catalysis of Diribonucleoside Monophosphate Cleavage by Water Soluble Copper(II) Complexes of Calix[4]arene Based Nitrogen Ligands
  作者：Roberta Cacciapaglia、Alessandro Casnati、Luigi Mandolini、David N. Reinhoudt、Riccardo Salvio、Andrea Sartori、Rocco Ungaro

  DOI：10.1021/ja0632106

  日期：2006.9.1

  Calix[4]arenes functionalized at the 1,2-, 1,3-, and 1,2,3-positions of the upper rim with [12]ane-N-3 ligating units were synthesized, and their bi-and trimetallic zinc(II) and copper( II) complexes were investigated as catalysts in the cleavage of phosphodiesters as RNA models. The results of comparative kinetic studies using monometallic controls indicate that the subunits of all of the zinc(II) complexes and of the 1,3-distal bimetallic copper(II) complex 7-Cu-2 act as essentially independent monometallic catalysts. The lack of cooperation between metal ions in the above complexes is in marked contrast with the behavior of the 1,2-vicinal bimetallic copper(II) complex 6-Cu-2, which exhibits high catalytic efficiency and high levels of cooperation between metal ions in the cleavage of HPNP and of diribonucleoside monophosphates NpN'. A third ligated metal ion at the upper rim does not enhance the catalytic efficiency, which excludes the simultaneous cooperation in the catalysis of the three metal ions in 8-Cu-3. Rate accelerations relative to the background brought about by 6-Cu-2 and 8-Cu-3 (1.0 mM catalyst, water solution, pH 7.0, 50 degrees C) are on the order of 10(4)-fold, largely independent of the nucleobase structure, with the exception of the cleavage of diribonucleoside monophosphates in which the nucleobase N is uracil, namely UpU and UpG, for which rate enhancements rise to 10(5)-fold. The rationale for the observed selectivity is discussed in terms of deprotonation of the uracil moiety under the reaction conditions and complexation of the resulting anion with one of the copper(II) centers.
• The p<i>K</i>_a of the Internucleotidic 2‘-Hydroxyl Group in Diribonucleoside (3‘→5‘) Monophosphates
  作者：S. Acharya、A. Földesi、J. Chattopadhyaya

  DOI：10.1021/jo026545o

  日期：2003.3.1

  Ionization of the internucleotidic 2'-hydroxyl group in RNA facilitates transesterification reactions in Group I and II introns (splicing), hammerhead and hairpin ribozymes, self-cleavage in lariat-RNA, and leadzymes and tRNA processing by RNase P RNA, as well as in some RNA cleavage reactions promoted by ribonucleases. Earlier, the pK(a) of 2'-OH in mono- and diribonucleoside (3'-->5') monophosphates had been measured under various nonuniform conditions, which make their comparison difficult. This work overcomes this limitation by measuring the pK(a) values for internucleotidic 2'-OH of eight different diribonucleoside (3'-5') monophosphates under a set of uniform noninvasive conditions by H-1 NMR. Thus the pK(a) is 12.31 (+/-0.02) for ApG and 12.41 (+/-0.04) for ApA, 12.73 (+/-0.04) for GpG and 12.71 (+/-0.08) for GpA, 12.77 (+/-0.03) for CpG and 12.88 (+/-0.02) for CpA, and 12.76 (+/-0.03) for UpG and 12.70 (+/-0.03) for UpA. By comparing the pK(a)s of the respective 2'-OH of monomeric nucleoside 3'-ethyl phosphates with that of internucleotidic 2'-OH in corresponding diribonucleoside (3'-5') monophosphates, it has been confirmed that the aglycons have no significant effect on the pKa values of their 2'-OH under our measurement condition, except for the internucleotidic 2'-OH of 9-adeninyl nucleotide at the 5'-end (ApA and ApG), which is more acidic by 0.3-0.4 pK(a) units.
• Sequence-dependent platinum chelation by adenylyl(3'-5')guanosine and guanylyl(3'-5')adenosine reacting with cis-diamminedichloroplatinum(II) and its diaqua derivative
  作者：Bruno Van Hemelryck、Jean Pierre Girault、Genevieve Chottard、Philippe Valadon、Abdelazize Laoui、Jean Claude Chottard

  DOI：10.1021/ic00253a003

  日期：1987.3
• Jamoulle; Torrence, European Journal of Medicinal Chemistry, 1986, vol. 21, # 6, p. 517 - 519
  作者：Jamoulle、Torrence

  DOI：——

  日期：——
• KOMIYAMA, MAKOTO;TAKESHIGE, YUICHI, J. ORG. CHEM., 54,(1989) N0, C. 4936-4939
  作者：KOMIYAMA, MAKOTO、TAKESHIGE, YUICHI

  DOI：——

  日期：——