5-phenylethynyl-3-(β-D-ribofuranosyl)pyridin-2-one | 697225-03-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-phenylethynyl-3-(β-D-ribofuranosyl)pyridin-2-one
• 英文别名: 3-(β-D-ribofuranosyl)-5-(2-phenylethynyl)-pyridin-2(1H)-one；3-(beta-D-ribofuranosyl)-5-(2-phenylethynyl)-pyridin-2(1H)-one；3-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(2-phenylethynyl)-1H-pyridin-2-one
• CAS: 697225-03-9
• 化学式: C₁₈H₁₇NO₅
• 分子量: 327.337
• InChiKey: OTEHCWIXFVWGBT-VQHPVUNQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 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：

  5-phenylethynyl-3-(β-D-ribofuranosyl)pyridin-2-one 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 作用下， 反应 2.17h， 生成 5-phenylethynyl-3-(β-D-ribofuranosyl)pyridin-2-one 5-triphosphate
  参考文献：
  名称：

  Unnatural base pairs mediate the site-specific incorporation of an unnatural hydrophobic component into RNA transcripts

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2004.02.072
• 作为产物：
  描述：

  3-(β-D-ribofuranosyl)-2-oxo(1H)pyridine 在 copper(l) iodide 、 四(三苯基膦)钯 、 碘 、 sodium carbonate 、 三乙胺 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 5-phenylethynyl-3-(β-D-ribofuranosyl)pyridin-2-one
  参考文献：
  名称：

  Unnatural base pairs mediate the site-specific incorporation of an unnatural hydrophobic component into RNA transcripts

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2004.02.072

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。
• NUCLEOSIDES OR NUCLEOTIDES HAVING NOVEL UNNATURAL BASES AND USE THEREOF
  申请人：RIKEN

  公开号：EP1544294B8

  公开（公告）日：2014-03-19
• ARTIFICIAL RIBOSWITCH FOR CONTROLLING PRE-MRNA SPLICING
  申请人：Gaur Rajesh K.

  公开号：US20090170793A1

  公开（公告）日：2009-07-02

  The present invention relates to riboswitches that have been engineered to regulate pre-mRNA splicing. In particular, the insertion of a high affinity theophylline binding aptamer into the 3′ splice site region, 5′ splice site region, or branchpoint sequence (BPS) of a pre-mRNA modulates RNA splicing in the presence of theophylline. Accordingly, the aspects of the present invention include, but are not limited to, theophylline-dependent riboswitches which modulate RNA splicing, methods of modulating RNA splicing using theophylline and its corresponding riboswitches, methods of improving/identifying theophylline-dependent riboswitches, methods of treating diseases associated with or caused by abnormal RNA splicing.
• US7563601B1
  申请人：——

  公开号：US7563601B1

  公开（公告）日：2009-07-21