3-(β-D-ribofuranosyl)-5-[3-(6-aminohexanamido)-1-propynyl]-2-oxo(1H)pyridine 5'-triphosphoric acid | 872610-23-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(β-D-ribofuranosyl)-5-[3-(6-aminohexanamido)-1-propynyl]-2-oxo(1H)pyridine 5'-triphosphoric acid
• 英文别名: [[(2R,3S,4R,5S)-5-[5-[3-(6-aminohexanoylamino)prop-1-ynyl]-2-oxo-1H-pyridin-3-yl]-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate
• CAS: 872610-23-6
• 化学式: C₁₉H₃₀N₃O₁₅P₃
• 分子量: 633.38
• InChiKey: QTTNYHCNHDCZJS-DDBAPUKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -8.6
• 重原子数：
  40
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  294
• 氢给体数：
  9
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  3-(β-D-ribofuranosyl)-5-[3-(6-aminohexanamido)-1-propynyl]-2-oxo(1H)pyridine 5'-triphosphoric acid 、 5-carboxyfluorescein N-hydroxysuccinimide ester 在 碳酸氢钠 、 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 以30%的产率得到3-(β-D-ribofuranosyl)-5-[3-[6-(fluorescein-5-carboxamido)hexanamido]-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-[3-(6-trifluoroacetamidohexanamido)-1-propynyl]-2-oxo(1H)pyridine 在 吡啶 、 二氯乙酸 、 ammonium hydroxide 、 2-氯-1,3,2-苯并二氧磷杂环己烷-4-酮 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.84h， 生成 3-(β-D-ribofuranosyl)-5-[3-(6-aminohexanamido)-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

文献信息

• Site-Specific Fluorescent Labeling of RNA Molecules by Specific Transcription Using Unnatural Base Pairs
  作者：Rie Kawai、Michiko Kimoto、Shuji Ikeda、Tsuneo Mitsui、Masayuki Endo、Shigeyuki Yokoyama、Ichiro Hirao

  DOI：10.1021/ja0542946

  日期：2005.12.1

  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.