3-(2,3-di-O-acetyl-β-D-ribofuranosyl)-5-[3-(2,2-dichloroacetamido)-1-propynyl]-2-oxo(1H)pyridine | 872610-17-8

• 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: 3-(2,3-di-O-acetyl-β-D-ribofuranosyl)-5-[3-(2,2-dichloroacetamido)-1-propynyl]-2-oxo(1H)pyridine
• 英文别名: [(2R,3R,4S,5S)-4-acetyloxy-5-[5-[3-[(2,2-dichloroacetyl)amino]prop-1-ynyl]-2-oxo-1H-pyridin-3-yl]-2-(hydroxymethyl)oxolan-3-yl] acetate
• CAS: 872610-17-8
• 化学式: C₁₉H₂₀Cl₂N₂O₈
• 分子量: 475.282
• InChiKey: CPIDTDFFVALXQG-QXSJWSMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  140
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-(2,3-di-O-acetyl-β-D-ribofuranosyl)-5-[3-(2,2-dichloroacetamido)-1-propynyl]-2-oxo(1H)pyridine 在 吡啶 、 ammonium hydroxide 、 2-氯-1,3,2-苯并二氧磷杂环己烷-4-酮 、 碳酸氢钠 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.59h， 生成 3-(β-D-ribofuranosyl)-5-[3-(fluorescein-5-carboxamido)-1-propynyl]-2-oxo(1H)pyridine 5'-triphosphoric acid
  参考文献：
  名称：

  Site-Specific Fluorescent Labeling of RNA Molecules by Specific Transcription Using Unnatural Base Pairs

  摘要：

  Site-specific fluorescent labeling of RNA molecules was achieved by specific transcription using an unnatural base pair system. The unnatural base pairs between 2-amino-6-(2-thienyl)purine (s) and 2-oxo-(1H)pyridine (y), and 2-amino-6-(2-thiazolyl)purine (v) and y function in transcription, and the substrates of y and 5-modified y bases can be site-specifically incorporated into RNA, opposite s or v in DNA templates, by T7 RNA polymerase. Ribonucleoside 5'-triphosphates of 5-fluorophore-linked y bases were chemically synthesized from the nucleoside of y. These fluorescent substrates were site-specifically incorporated into RNA by transcription mediated by the s-y and v-y pairs. By using this fluorescent labeling method, specific positions of Raf-binding and theophylline-binding RNA aptamers were fluorescently labeled, and the specific binding to their target molecules was detected by their fluorescent intensities. This site-specific labeling method using an unnatural base pair system will be useful for analyzing conformational changes of RNA molecules and for detecting interactions between RNA and its binding species.

  DOI：

  10.1021/ja0542946
• 作为产物：
  描述：

  3-(2,3-di-O-acetyl-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl)-5-iodo-2-oxo(1H)pyridine 在 二氯乙酸 、 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.75h， 生成 3-(2,3-di-O-acetyl-β-D-ribofuranosyl)-5-[3-(2,2-dichloroacetamido)-1-propynyl]-2-oxo(1H)pyridine
  参考文献：
  名称：

  Site-Specific Fluorescent Labeling of RNA Molecules by Specific Transcription Using Unnatural Base Pairs

  摘要：

  Site-specific fluorescent labeling of RNA molecules was achieved by specific transcription using an unnatural base pair system. The unnatural base pairs between 2-amino-6-(2-thienyl)purine (s) and 2-oxo-(1H)pyridine (y), and 2-amino-6-(2-thiazolyl)purine (v) and y function in transcription, and the substrates of y and 5-modified y bases can be site-specifically incorporated into RNA, opposite s or v in DNA templates, by T7 RNA polymerase. Ribonucleoside 5'-triphosphates of 5-fluorophore-linked y bases were chemically synthesized from the nucleoside of y. These fluorescent substrates were site-specifically incorporated into RNA by transcription mediated by the s-y and v-y pairs. By using this fluorescent labeling method, specific positions of Raf-binding and theophylline-binding RNA aptamers were fluorescently labeled, and the specific binding to their target molecules was detected by their fluorescent intensities. This site-specific labeling method using an unnatural base pair system will be useful for analyzing conformational changes of RNA molecules and for detecting interactions between RNA and its binding species.

  DOI：

  10.1021/ja0542946

文献信息

• NOVEL NUCLEOSIDE OR NUCLEOTIDE DERIVATIVE AND USE THEREOF
  申请人：Riken

  公开号：EP1816130A1

  公开（公告）日：2007-08-08

  The object of the present invention is to provide a nucleoside or nucleotide having a 5-substituted-2-oxo(1H)pyridin-3-yl group as a base, as well as a method using the same. In one embodiment, the nucleoside or nucleotide of the present invention has a fluorescent dye selected from the group consisting of 5-FAM, 6-FAM, 5-TAMRA, 6-TAMRA, DANSYL, 5-HEX, 6-HEX, 5-TET, 6-TET, 5-ROX and 6-ROX or a quencher dye selected from the group consisting of DABCYL. BHQ1 and BHQ2, which is attached either directly or through a linker to the 5-position of the above base.

  本发明的目的是提供一种以5-取代-2-氧代(1H)吡啶-3-基团为碱基的核苷或核苷酸，以及使用这种核苷或核苷酸的方法。 在一个实施方案中，本发明的核苷或核苷酸具有选自 5-FAM、6-FAM、5-TAMRA、6-TAMRA、DANSYL、5-HEX、6-HEX、5-TET、6-TET、5-ROX 和 6-ROX 组成的组的荧光染料或选自 DABCYL.BHQ1 和 BHQ2，它们直接或通过连接体连接到上述碱基的 5 位。
• EP1816130
  申请人：——

  公开号：——

  公开（公告）日：——
• Novel Nucleoside or Nucleotide Derivative and Use Thereof
  申请人：Hirao Ichiro

  公开号：US20090275017A1

  公开（公告）日：2009-11-05

  The object of the present invention is to provide a nucleoside or nucleotide having a 5-substituted-2-oxo(1H)pyridin-3-yl group as a base, as well as a method using the same. In one embodiment, the nucleoside or nucleotide of the present invention has a fluorescent dye selected from the group consisting of 5-FAM, 6-FAM, 5-TAMRA, 6-TAMRA, DANSYL, 5-HEX, 6-HEX, 5-TET, 6-TET, 5-ROX and 6-ROX or a quencher dye selected from the group consisting of DABCYL, BHQ1 and BHQ2, which is attached either directly or through a linker to the 5-position of the above base.
• US7960543B2
  申请人：——

  公开号：US7960543B2

  公开（公告）日：2011-06-14