3-(β-D-ribofuranosyl)-2-oxo(1H)pyridine | 114072-10-5

• 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)-2-oxo(1H)pyridine
• 英文别名: 3-(β-D-ribofuranosyl)-pyridine-2-one；3-(β-D-ribofuranosyl)-pyridin-2(1H)-one；3-(beta-D-Ribofuranosyl)-pyridin-2(1H)-one；3-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-pyridin-2-one
• CAS: 114072-10-5
• 化学式: C₁₀H₁₃NO₅
• 分子量: 227.217
• InChiKey: XZCXSJCRXFBVPI-BGZDPUMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  16
• 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)-2-oxo(1H)pyridine 在 吡啶 、 二氯乙酸 、 ammonium hydroxide 、 N-碘代丁二酰亚胺 、 copper(l) iodide 、 四(三苯基膦)钯 、 2-氯-1,3,2-苯并二氧磷杂环己烷-4-酮 、 碳酸氢钠 、 sodium carbonate 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 28.84h， 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：

  5-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribono-1,4-lactone 在 氢氧化钾 、 sodium tetrahydroborate 、 碘代三甲硅烷 、 四丁基氟化铵 、 溶剂黄146 、 三苯基膦 、 lithium diisopropyl amide 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 27.0h， 生成 3-(β-D-ribofuranosyl)-2-oxo(1H)pyridine
  参考文献：
  名称：

  3-（β-D-呋喃核糖基）-2-氟吡啶和3-（β-D-呋喃核糖基）-吡啶-2-酮的合成

  摘要：

  吡啶-2-酮C-核苷13分7个步骤由2-氟吡啶1和D-ribono-1,4-lactone 2制备。β-核糖呋喃糖苷12和13的成功方法包括还原半缩醛3的呋喃糖环，然后进行分子内光延环化。

  DOI：

  10.1016/s0040-4039(96)02289-7

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。
• Novel nucleic acid base pair
  申请人：Hirao Ichiro

  公开号：US20090286247A1

  公开（公告）日：2009-11-19

  A novel artificial nucleic acid base pair which is obtained by forming a selective base pair by introducing a group having steric hindrance (preferably a group having steric hindrance and static repulsion and a stacking effect) and can be recognized by a polymerase such as DNA polymerase; a novel artificial gene; and a method of designing nucleic acid bases so as to form a selective base pair with the use of steric hindrance, static repulsion and stacking effect at the base moiety of the nucleic acid. An artificial nucleic acid comprising these bases; a process for producing the same; a codon containing the same; a nucleic acid molecule containing the same; a process for producing a non-natural gene by using the same; a process for producing a novel protein by using the above nucleic acid molecule or non-natural gene, and the like.

  一种新型人工核酸碱基对，通过引入具有立体位阻（优选为具有立体位阻和静电斥力以及堆积效应）的基团形成选择性碱基对，并且可以被聚合酶如DNA聚合酶识别；一种新型人工基因；以及一种设计核酸碱基的方法，以便在核酸的碱基部分利用立体位阻、静电斥力和堆积效应形成选择性碱基对。包含这些碱基的人工核酸；制备该人工核酸的方法；包含该人工核酸的密码子；包含该人工核酸的核酸分子；使用该人工核酸制备非天然基因的方法；使用上述核酸分子或非天然基因制备新型蛋白质的方法等。
• 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。
• Ribozymes directed against flt-1
  申请人：RIBOZYME PHARMACEUTICALS, INC.

  公开号：EP1321521A1

  公开（公告）日：2003-06-25

  Nucleic acid catalysts which modulate the expression of flt-1 gene; methods of delivery, screening, identification, synthesis, deprotection, purification of nucleic acid catalysts and process for identification of nucleic acid molecules is described.

  描述了调节 flt-1 基因表达的核酸催化剂；核酸催化剂的递送、筛选、鉴定、合成、脱保护、纯化方法以及核酸分子的鉴定过程。
• 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。