2-[(phenoxyacetyl)amino]-9-(2'-deoxy-β-D-ribofuranosyl)-6-(2-methylthioethyl)purine | 833486-77-4

• 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: 2-[(phenoxyacetyl)amino]-9-(2'-deoxy-β-D-ribofuranosyl)-6-(2-methylthioethyl)purine
• 英文别名: 2-phenoxyacetylamino-9-(2'-deoxy-D-ribofyranosyl)-6-(2-methylthioethyl)purine；N-[9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-(2-methylsulfanylethyl)purin-2-yl]-2-phenoxyacetamide
• CAS: 833486-77-4
• 化学式: C₂₁H₂₅N₅O₅S
• 分子量: 459.526
• InChiKey: YTVDVQOGJQEEBX-LZLYRXPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  157
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-[(phenoxyacetyl)amino]-9-(2'-deoxy-β-D-ribofuranosyl)-6-(2-methylthioethyl)purine 在 磷酸三甲酯 、 1,8-双二甲氨基萘 、 三氯氧磷 、 三正丁胺 、 三丁基焦磷酸铵 、 水 、 三乙基碳酸氢铵缓冲液 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成
  参考文献：
  名称：

  Incorporation of an inducible nucleotide analog into DNA by DNA polymerases

  摘要：

  Non-natural nucleotides with diverse functionalities are highly useful in many areas of basic research and practical applications. We have previously developed an efficient method for post-synthetic modifications of 2-amino-6-vinylpurine (AVP)-containing oligonucleotides, which permits conjugations of a variety of useful functional appendages to the AVP moiety in DNA. Here we report an investigation on the ability of various DNA polymerases to use 5'-triphosphate of 2'-deoxyribosyl-2-amino-6-(2-methylthioethyl)purine (a stable precursor of AVP) as the substrate for templated DNA synthesis. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.02.024
• 作为产物：
  描述：

  2-amino-9-(3',5'-di-O-tert-butyldimethylsilyl-2'-deoxy-β-D-ribofuranosyl)-6-vinylpurine 在 吡啶 、 四丁基氟化铵 、 1-羟基苯并三唑 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 4.33h， 生成 2-[(phenoxyacetyl)amino]-9-(2'-deoxy-β-D-ribofuranosyl)-6-(2-methylthioethyl)purine
  参考文献：
  名称：

  杂交促进和胞嘧啶选择性活化与2-氨基-6-乙烯基嘌呤衍生物的交联

  摘要：

  最近，我们提出了具有可诱导反应性的交联剂的新概念，其中可以从其稳定的前体原位再生高反应性的交联剂2-氨基-6-乙烯基嘌呤核苷类似物（1）。苯硫醚（4）和苯亚砜（3）衍生物，通过杂交促进的活化过程，对胞苷具有选择性。尽管苯硫醚前体（4）对强亲核试剂（如胺和硫醇）具有很高的稳定性，但仍显示出交联能力。在这项研究中，我们研究了苯硫基对交联反应的取代作用，并确定了苯硫衍生物的2-羧基取代基（11k）作为具有可诱导反应性的有效交联剂。详细的研究表明，苯亚砜（3）和苯硫醚（4）的前体会产生2-氨基-6-乙烯基嘌呤核苷（1）作为常见的反应性物质。已经得出结论，前体（3和4）的可诱导反应性的性质是通过在ODN中具有胞嘧啶核苷的ODN在双链中的选择性过程，加速了它们对2-氨基-6-乙烯基嘌呤核苷（1）的消除。目标站点。

  DOI：

  10.1021/jo048298p

文献信息

• The alkyl-connected 2-amino-6-vinylpurine (AVP) crosslinking agent for improved selectivity to the cytosine base in RNA
  作者：Yosuke Taniguchi、Yusuke Kurose、Takamasa Nishioka、Fumi Nagatsugi、Shigeki Sasaki

  DOI：10.1016/j.bmc.2010.03.008

  日期：2010.4

  We have previously reported that the 2-amino-6-vinylpurine (AVP) nucleoside exhibits a highly efficient and selective crosslinking reaction toward cytosine and displayed an improved antisense inhibition in cultured cells. In this study, we further investigated the alkyl-connected AVP nucleoside analogs for more efficient crosslinking to the cytosine base (rC) of the target RNA. We synthesized three AVP analogs which connect the 2-amino-6-vinylpurine unit to the 2'-deoxyribose through a methylene, an ethylene, or a butylene linker. The ODN incorporating the AVP analog with the methylene or the butylene linker showed a slightly higher crosslinking to the target rC of RNA than the original AVP with no linker. In contrast, the AVP with the ethylene linker formed a selective and efficient crosslink to the rC of the target RNA. (C) 2010 Elsevier Ltd. All rights reserved.
• Hybridization-Promoted and Cytidine-Selective Activation for Cross-Linking with the Use of 2-Amino-6-vinylpurine Derivatives
  作者：Takeshi Kawasaki、Fumi Nagatsugi、Md. Monsur Ali、Minoru Maeda、Kumiko Sugiyama、Kenji Hori、Shigeki Sasaki

  DOI：10.1021/jo048298p

  日期：2005.1.1

  Recently, we have proposed a new concept for cross-linking agents with inducible reactivity, in which the highly reactive cross-linking agent, the 2-amino-6-vinylpurine nucleoside analogue (1), can be regenerated in situ from its stable precursors, the phenylsulfide (4) and the phenylsulfoxide (3) derivatives, by a hybridization-promoted activation process with selectivity to cytidine. The phenylsulfide precursor

  最近，我们提出了具有可诱导反应性的交联剂的新概念，其中可以从其稳定的前体原位再生高反应性的交联剂2-氨基-6-乙烯基嘌呤核苷类似物（1）。苯硫醚（4）和苯亚砜（3）衍生物，通过杂交促进的活化过程，对胞苷具有选择性。尽管苯硫醚前体（4）对强亲核试剂（如胺和硫醇）具有很高的稳定性，但仍显示出交联能力。在这项研究中，我们研究了苯硫基对交联反应的取代作用，并确定了苯硫衍生物的2-羧基取代基（11k）作为具有可诱导反应性的有效交联剂。详细的研究表明，苯亚砜（3）和苯硫醚（4）的前体会产生2-氨基-6-乙烯基嘌呤核苷（1）作为常见的反应性物质。已经得出结论，前体（3和4）的可诱导反应性的性质是通过在ODN中具有胞嘧啶核苷的ODN在双链中的选择性过程，加速了它们对2-氨基-6-乙烯基嘌呤核苷（1）的消除。目标站点。
• Incorporation of an inducible nucleotide analog into DNA by DNA polymerases
  作者：Md. Monsur Ali、Shuhei Imoto、Yingfu Li、Shigeki Sasaki、Fumi Nagatsugi

  DOI：10.1016/j.bmc.2009.02.024

  日期：2009.4

  Non-natural nucleotides with diverse functionalities are highly useful in many areas of basic research and practical applications. We have previously developed an efficient method for post-synthetic modifications of 2-amino-6-vinylpurine (AVP)-containing oligonucleotides, which permits conjugations of a variety of useful functional appendages to the AVP moiety in DNA. Here we report an investigation on the ability of various DNA polymerases to use 5'-triphosphate of 2'-deoxyribosyl-2-amino-6-(2-methylthioethyl)purine (a stable precursor of AVP) as the substrate for templated DNA synthesis. (c) 2009 Elsevier Ltd. All rights reserved.