9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-2-amino-6-N,N-dimethylaminopurine | 79999-41-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-2-amino-6-N,N-dimethylaminopurine
• 英文别名: 2-amino-6-(N,N-dimethylamino)-9-(2',3,5'-tri-O-acetyl-beta-D-ribofuranosyl]purine；[(2R,3R,4R,5R)-3,4-diacetyloxy-5-[2-amino-6-(dimethylamino)purin-9-yl]oxolan-2-yl]methyl acetate
• CAS: 79999-41-0
• 化学式: C₁₈H₂₄N₆O₇
• 分子量: 436.425
• InChiKey: GKPKKLWKKUIADT-LSCFUAHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  161
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-2-amino-6-N,N-dimethylaminopurine 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydroxide 、 偶氮二异丁腈 、 四丁基氟化铵 、 三正丁基氢锡 作用下， 生成 N-[6-(dimethylamino)-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-2-yl]benzamide
  参考文献：
  名称：

  Synthesis of 3-(2-deoxy-β-d-ribofuranosyl)pyridin-2-one and 2-amino-6-(N,N-dimethylamino)-9-(2-deoxy-β-d-ribofuranosyl)purine derivatives for an unnatural base pair

  摘要：

  An unnatural base pair, 2-amino-6-(N,N-dimethylamino)purine (denoted x) and pyridin-2-one (denoted y), was designed to prove the structural requirements for base pair formation involving shape complementarity. It was expected that y might satisfy the structural requirements for pairing with x, in which the bulky 6-dimethylamino group may eliminate base pairing with the natural bases. As chemical or biological substrates for DNA synthesis, the phosphoramidite of x and the 2'-deoxy-C3-ribonucleoside triphosphate of y (dyTP) were synthesized, and the incorporation experiment was demonstrated by using the Klenow fragment of Escherichia call DNA polymerase I. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00520-7
• 作为产物：
  描述：

  2',3',5'-三乙酰鸟苷 在 四乙基氯化铵 、 N,N-二甲基苯胺 、 三氯氧磷 作用下， 以 乙腈 为溶剂， 反应 28.17h， 生成 9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-2-amino-6-N,N-dimethylaminopurine
  参考文献：
  名称：

  Nucleic acid related compounds. 33. Conversions of adenosine and guanosine to 2,6-dichloro, 2-amino-6-chloro, and derived purine nucleosides

  摘要：

  腺苷1-N-氧化物经酶促脱氨基作用生成1-羟基次黄嘌呤（2a），随后乙酰化并氯化得到2,6-二氯-9-(2,3,5-三-O-乙酰-(β-D-核糖呋喃糖基)嘌呤（3）。干燥的1,2-二甲氧基乙烷中的氨转化3为2-氯腺苷三乙酸酯（4a）。在乙腈中，用三甲胺在高温下处理4a导致形成2-N,N-二甲基氨基腺苷三乙酸酯（4b）。瓜嘌呤（5）通过改进的方法顺利地被乙酰化。得到的三乙酸酯（6）在约85%的产率下氯化，生成2-氨基-6-氯-9-(2,3,5-三-O-乙酰-β-D-核糖呋喃糖基)嘌呤（7）。用三甲胺在室温下处理7 28小时，得到6-N,N-二甲基氨基化合物（8d）。然而，钾氟化物或氯化钠与DMF或乙腈中的催化量三甲胺反应，产率大于90%地生成2-氨基-6-氟（8a）或2-氨基-6-叠氮（8b）产物。

  DOI：

  10.1139/v81-374

文献信息

• Novel nucleic acid base pair
  申请人：Hirao Ichiro

  公开号：US20050191689A1

  公开（公告）日：2005-09-01

  A novel artificial nucleic acid base pair which is obtained by forming a selective base pair by introducing a group having steric hindrance (preferably a group having steric hindrance and static repulsion and a stacking effect) and can be recognized by a polymerase such as DNA polymerase; a novel artificial gene; and a method of designing nucleic acid bases so as to form a selective base pair with the use of steric hindrance, static repulsion and stacking effect at the base moiety of the nucleic acid. An artificial nucleic acid comprising these bases; a process for producing the same; a codon containing the same; a nucleic acid molecule containing the same; a process for producing a non-natural gene by using the same; a process for producing a novel protein by using the above nucleic acid molecule or non-natural gene, and the like.

  一种新的人工核酸碱基对，通过引入具有立体位阻的基团（优选具有立体位阻和静电斥力以及堆积效应的基团），形成选择性碱基对，并能被DNA聚合酶等聚合酶识别；一种新的人工基因；以及一种设计核酸碱基的方法，以便利用核酸的碱基部分的立体位阻、静电斥力和堆积效应形成选择性碱基对。包括这些碱基的人工核酸；生产该核酸的过程；含有该核酸的密码子；含有该核酸的核酸分子；利用该核酸分子或非天然基因生产非天然基因的过程；利用上述核酸分子或非天然基因生产新型蛋白质的过程等。
• Nucleic acid base pair
  申请人：Japan Science and Technology Agency

  公开号：US07667031B2

  公开（公告）日：2010-02-23

  A novel artificial nucleic acid base pair which is obtained by forming a selective base pair by introducing a group having steric hindrance (preferably a group having steric hindrance and static repulsion and a stacking effect) and can be recognized by a polymerase such as DNA polymerase; a novel artificial gene; and a method of designing nucleic acid bases so as to form a selective base pair with the use of steric hindrance, static repulsion and stacking effect at the base moiety of the nucleic acid. An artificial nucleic acid comprising these bases; a process for producing the same; a codon containing the same; a nucleic acid molecule containing the same; a process for producing a non-natural gene by using the same; a process for producing a novel protein by using the above nucleic acid molecule or non-natural gene, and the like.

  一种新型人工核酸碱基对，通过引入具有空间位阻的基团（最好是具有空间位阻、静电排斥和堆积效应的基团），形成一种选择性碱基对，并可以被聚合酶如DNA聚合酶识别；一种新型人工基因；以及一种设计核酸碱基的方法，以利用核酸碱基的基团上的空间位阻、静电排斥和堆积效应形成选择性碱基对。包含这些碱基的人工核酸；生产该人工核酸的方法；包含该核酸的密码子；包含该核酸的核酸分子；使用该核酸分子或非自然基因生产非自然基因的方法；使用上述核酸分子或非自然基因生产新型蛋白质的方法等。
• Nucleic acid related compounds. 33. Conversions of adenosine and guanosine to 2,6-dichloro, 2-amino-6-chloro, and derived purine nucleosides
  作者：Morris J. Robins、Bogdan Uznański

  DOI：10.1139/v81-374

  日期：1981.9.1

  Enzymatic deamination of adenosine 1-N-oxide gave 1-hydroxyinosine (2a) which was acetylated and then chlorinated to give 2,6-dichloro-9-(2,3,5-tri-O-acetyl-(β-D-ribofuranosyl)purine (3). Ammonia in dry 1,2-dimethoxyethane converted 3 into 2-chloro-adenosine triacetate (4a). Treatment of 4a with trimethylamine at elevated temperatures in acetonitrile resulted in formation of 2-N,N-dimethylaminoadenosine triacetate (4b). Guanosine (5) was acetylated smoothly by an improved procedure. The resulting triacetate (6) was chlorinated in ∼85% yield to give 2-amino-6-chloro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine (7). Treatment of 7 with trimethylamine at ambient temperature for 28 hours gave the 6-N,N-dimethylamino compound (8d). However, potassium fluoride or sodium azide with catalytic quantities of trimethylamine in DMF or acetonitrile gave the 2-amino-6-fluoro (8a) or 2-amino-6-azido (8b) products in yields of greater than 90%.

  腺苷1-N-氧化物经酶促脱氨基作用生成1-羟基次黄嘌呤（2a），随后乙酰化并氯化得到2,6-二氯-9-(2,3,5-三-O-乙酰-(β-D-核糖呋喃糖基)嘌呤（3）。干燥的1,2-二甲氧基乙烷中的氨转化3为2-氯腺苷三乙酸酯（4a）。在乙腈中，用三甲胺在高温下处理4a导致形成2-N,N-二甲基氨基腺苷三乙酸酯（4b）。瓜嘌呤（5）通过改进的方法顺利地被乙酰化。得到的三乙酸酯（6）在约85%的产率下氯化，生成2-氨基-6-氯-9-(2,3,5-三-O-乙酰-β-D-核糖呋喃糖基)嘌呤（7）。用三甲胺在室温下处理7 28小时，得到6-N,N-二甲基氨基化合物（8d）。然而，钾氟化物或氯化钠与DMF或乙腈中的催化量三甲胺反应，产率大于90%地生成2-氨基-6-氟（8a）或2-氨基-6-叠氮（8b）产物。
• Synthesis of 3-(2-deoxy-β-d-ribofuranosyl)pyridin-2-one and 2-amino-6-(N,N-dimethylamino)-9-(2-deoxy-β-d-ribofuranosyl)purine derivatives for an unnatural base pair
  作者：Masahide Ishikawa、Ichiro Hirao、Shigeyuki Yokoyama

  DOI：10.1016/s0040-4039(00)00520-7

  日期：2000.5

  An unnatural base pair, 2-amino-6-(N,N-dimethylamino)purine (denoted x) and pyridin-2-one (denoted y), was designed to prove the structural requirements for base pair formation involving shape complementarity. It was expected that y might satisfy the structural requirements for pairing with x, in which the bulky 6-dimethylamino group may eliminate base pairing with the natural bases. As chemical or biological substrates for DNA synthesis, the phosphoramidite of x and the 2'-deoxy-C3-ribonucleoside triphosphate of y (dyTP) were synthesized, and the incorporation experiment was demonstrated by using the Klenow fragment of Escherichia call DNA polymerase I. (C) 2000 Elsevier Science Ltd. All rights reserved.