3-(β-D-ribofuranosyl)-5-iodo-2-oxo(1H)pyridine | 610766-50-2

• 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-iodo-2-oxo(1H)pyridine
• 英文别名: 3-(β-D-ribofuranosyl)-5-iodopyridin-2(1H)-one；3-(beta-D-ribofuranosyl)-5-iodopyridin-2(1H)-one；3-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodo-1H-pyridin-2-one
• CAS: 610766-50-2
• 化学式: C₁₀H₁₂INO₅
• 分子量: 353.113
• InChiKey: MABWFOPIGSZHLF-BGZDPUMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  99
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(β-D-ribofuranosyl)-5-iodo-2-oxo(1H)pyridine 在 吡啶 作用下， 反应 1.5h， 生成 3-(2,3-di-O-acetyl-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl)-5-iodo-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
• 作为产物：
  描述：

  3-(β-D-ribofuranosyl)-2-oxo(1H)pyridine 在 N-碘代丁二酰亚胺 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 2.0h， 生成 3-(β-D-ribofuranosyl)-5-iodo-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

• Nucleoside or nucleotides having novel unnatural bases and utilization of the same
  申请人：Hirao Ichiro

  公开号：US20060263771A1

  公开（公告）日：2006-11-23

  The object of the present invention is to provide a nucleoside or nucleotide having an unnatural base. The nucleoside or nucleotide of the present invention has a 5-substituted-2-oxo(1H)-pyridin-3-yl group as a base. Preferably, the 5-position of the above base is substituted with a substituent selected from the group consisting of the following: 1) a photoreactive group selected from iodine and bromine; 2) an alkenyl group, an alkynyl group or an amino group, or a derivative thereof; 3) biotin or a derivative thereof; and 4) a fluorescent molecule selected from fluorescein, 6-carboxyfluorescein, tetramethyl-6-carboxyrhodamine, and derivatives thereof.

  本发明的目的是提供一种具有非天然碱基的核苷或核苷酸。本发明的核苷或核苷酸具有5-取代-2-氧代（1H）-吡啶-3-基团作为碱基。优选地，上述碱基的5位被取代为以下群组中选择的取代基：1）光敏反应基团，选择自碘和溴；2）烯基基团，炔基基团或氨基基团或其衍生物；3）生物素或其衍生物；和4）荧光分子，选择自荧光素，6-羧基荧光素，四甲基-6-羧基罗丹明和其衍生物。
• Nucleosides or nucleotides having novel unnatural bases and use thereof
  申请人：RIKEN

  公开号：US07745417B2

  公开（公告）日：2010-06-29

  The object of the present invention is to provide a nucleoside or nucleotide having an unnatural base. The nucleoside or nucleotide of the present invention has a 5-substituted-2-oxo(1H)-pyridin-3-yl group as a base. Preferably, the 5-position of the above base is substituted with a substituent selected from the group consisting of the following: 1) a photoreactive group selected from iodine and bromine; 2) an alkenyl group, an alkynyl group or an amino group, or a derivative thereof; 3) biotin or a derivative thereof; and 4) a fluorescent molecule selected from fluorescein, 6-carboxyfluorescein, tetramethyl-6-carboxyrhodamine, and derivatives thereof.

  本发明的目的是提供一种具有非天然碱基的核苷酸或核苷。本发明的核苷酸或核苷具有5-取代-2-氧代(1H)-吡啶-3-基基团作为碱基。优选，上述基团的5-位置被以下组的取代基所取代：1）从碘和溴中选择的光反应基团；2）烯基基团、炔基基团或氨基、或其衍生物；3）生物素或其衍生物；和4）从荧光素、6-羧基荧光素、四甲基-6-羧基罗丹明和其衍生物中选择的荧光分子。
• 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。
• Unnatural base pairs mediate the site-specific incorporation of an unnatural hydrophobic component into RNA transcripts
  作者：Masayuki Endo、Tsuneo Mitsui、Taeko Okuni、Michiko Kimoto、Ichiro Hirao、Shigeyuki Yokoyama

  DOI：10.1016/j.bmcl.2004.02.072

  日期：2004.5

  Site-specific incorporation of a hydrophobic nucleotide analog into RNA, by T7 transcription mediated by unnatural base pairs, was developed. The nucleotide analog, 5-phenylethynyl-3-(beta-D-ribofuranosyl)pyridin-2-one 5-triphosphate (denoted by Ph-yTP), was chemically synthesized and then site-specifically incorporated by T7 RNA polymerase into RNA opposite the pairing partner, 2-amino-6-(2-thienyl)purine (denoted by s) in DNA templates. The introduction of Ph-y into a theophylline-binding RNA aptamer, in which a uridine in the internal loop was replaced by Ph-y, raised the thermal stability of the aptamer. Thus, this unnatural nucleotide analog would be useful for stabilizing RNA tertiary structures and complexes between RNA and other molecules. (C) 2004 Elsevier Ltd. All rights reserved.
• EP1816130
  申请人：——

  公开号：——

  公开（公告）日：——