<1',2',3',4',5'-13C5>-uridine | 159496-16-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: <1',2',3',4',5'-13C5>-uridine
• 英文别名: EIDD-2481；1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxy(113C)methyl)(2,3,4,5-13C4)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 159496-16-9
• 化学式: C₉H₁₂N₂O₆
• 分子量: 249.149
• InChiKey: DRTQHJPVMGBUCF-AWOURBBFSA-N

物化性质

• 熔点：
  166-168°C
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  119
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  <1',2',3',4',5'-13C5>-uridine 在 吡啶 、 silver nitrate 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 生成
  参考文献：
  名称：

  序列特异性非均匀13 C 5标记RNA的第一个例子：具有13 C弛豫窗的29mer HIV-1 TAR RNA的合成

  摘要：

  完整的合成方案以及有关单体结构单元的1 H和13 C-NMR数据，这些单体用于固相合成13 C标记（99％原子的13 C）茎（27 A和43 G），凸起（24 C）和环（31 29聚体HIV-1 RNA TAR发夹U）区域从起始13 ç 6 - -葡萄糖被呈现。的复杂的NMR谱13 C标记的单体结构单元，由于各种的相互作用13 C和1已指定H个旋转。异核2D NMR已证明，通过化学合成在此处实现的HIV-1 TAR 29mer RNA的非均一标记提供了最佳的机会，可以进行完整的T 1和T 2弛豫测量（“ NMR弛豫窗口”）与统一标记的寡核苷酸RNA相比，由于13 C共振的最小重叠，所有四种策略性地将13 C标记的残基的糖碳的每种类型均以独特且前所未有的方式进行。

  DOI：

  10.1016/s0040-4020(99)00294-x
• 作为产物：
  描述：

  (3aR,5R,6S,6aR)-5-(hydroxymethyl-13C)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl-3a,5,6,6a-13C4 methanesulfonate 在 4-二甲氨基吡啶 、 sodium hydroxide 、 硫酸 、 sodium acetate 、 四氯化锡 作用下， 以 吡啶 、 水 、 甲苯 为溶剂， 生成 <1',2',3',4',5'-13C5>-uridine
  参考文献：
  名称：

  13 C标记单体的化学合成，用于固相和模板控制的DNA和RNA低聚物的酶促合成

  摘要：

  从[ 13 C 6 ]-葡萄糖1和相应的核碱基5a-e或6a-e（N 6-苯甲酰基-腺嘌呤，N 2-乙酰基-鸟嘌呤，N 4-苯甲酰基-胞嘧啶）开始制备13 C标记的核糖核苷（尿嘧啶和胸腺嘧啶）的总收率在47％至66％之间。它们随后转化为5'- O-二甲氧基三苯甲基保护的DNA-亚磷酰胺和5'- O-二甲氧基三苯甲基-2' - O-三烷基甲硅烷基保护的RNA-磷-酰胺，用于固相合成DNA-和RNA-低聚物，并转化为5' - Ø已经进行了用于模板控制的酶促合成（聚合酶-或逆转录酶反应）的-核糖核苷和-核糖核苷三磷酸。

  DOI：

  10.1016/s0040-4039(00)73458-7

文献信息

• Synthesis of multiply labelled ribonucleosides for sequence-specific labelling of oligo-RNA
  作者：Jan Milecki、Andras Földesi、Artur Fischer、Ryszard W. Adamiak、Jyoti Chattopadhyaya

  DOI：10.1002/jlcr.503

  日期：2001.10.15

  The synthesis of ribonucleotide blocks multiply labelled with 2H, 13C and 15N for solid support synthesis of sequence specifically labelled RNA is described. Labels were introduced in the ribose ring (13C), C5 position of pyrimidine nucleobases (2H) and exocyclic amino groups (15N) and serve as multiple probes for studying the various physicochemical consequences of physiologically important RNA folding by high-resolution multi-nuclear NMR spectroscopy. Copyright © 2001 John Wiley & Sons, Ltd.

  本文描述了核糖核苷酸块与2H、13C和15N的复合标记，用于序列特异性标记的RNA的固体支持合成。标记被引入核糖环（13C）、嘧啶核苷酸的C5位（2H）和外环氨基（15N），并作为多重探针，用于通过高分辨率多核核磁共振光谱研究生理上重要的RNA折叠的各种物理化学后果。版权所有 © 2001 John Wiley & Sons, Ltd.
• The prophylactic and therapeutic activity of a broadly active ribonucleoside analog in a murine model of intranasal venezuelan equine encephalitis virus infection
  作者：George R. Painter、Richard A. Bowen、Gregory R. Bluemling、John DeBergh、Vindhya Edpuganti、Prabhakar R. Gruddanti、David B. Guthrie、Michael Hager、Damien L. Kuiper、Mark A. Lockwood、Deborah G. Mitchell、Michael G. Natchus、Zachary M. Sticher、Alexander A. Kolykhalov

  DOI：10.1016/j.antiviral.2019.104597

  日期：2019.11

  The New World alphaviruses Venezuelan, Eastern, and Western equine encephalitis viruses (VEEV, EEEV and WEEV, respectively) commonly cause a febrile disease that can progress to meningoencephalitis, resulting in significant morbidity and mortality. To address the need for a therapeutic agent for the treatment of Alphavirus infections, we identified and pursued preclinical characterization of a ribonucleoside analog EIDD-1931 (beta-D-N-4-hydroxycytidine, NHC), which has shown broad activity against alphaviruses in vitro and has a very high genetic barrier for development of resistance. To be truly effective as a therapeutic agent for VEEV infection a drug must penetrate the blood brain barrier and arrest virus replication in the brain. High plasma levels of EIDD-1931 are rapidly achieved in mice after oral dosing. Once in the plasma EIDD-1931 is efficiently distributed into organs, including brain, where it is rapidly converted to its active 5'-triphosphate. EIDD-1931 showed a good safety profile in mice after 7-day repeated dosing with up to 1000 mg/kg/day doses. In mouse model studies, EIDD-1931 was 90-100% effective in protecting mice against lethal intranasal infection when therapeutic treatment was started as late as 24 h post-infection, and partial protection was achieved when treatment was delayed for 48 h post-infection. These results support further preclinical development of EIDD-1931 as a potential anti-alphavirus drug.
• Chemical synthesis of 13C-labelled monomers for the solid-phase and template controlled enzymatic synthesis of DNA and RNA oligomers
  作者：S. Quant、R.W. Wechselberger、M.A. Wolter、K.-H. Wörner、P. Schell、J.W. Engels、C. Griesinger、H. Schwalbe

  DOI：10.1016/s0040-4039(00)73458-7

  日期：1994.9

  5′-O-dimethoxytrityl protected DNA-phosphoramidites and 5′-O-dimethoxytrityl-2′-O-trialkylsilyl protected RNA-phosphor-amidites for the solid phase synthesis of DNA- and RNA-oligomers and to 5′-O-ribo- and deoxyribo-nucleosidetriphosphates for template controlled enzymatic synthesis (polymerase- or reverse transcriptase reaction) has been carried out.

  从[ 13 C 6 ]-葡萄糖1和相应的核碱基5a-e或6a-e（N 6-苯甲酰基-腺嘌呤，N 2-乙酰基-鸟嘌呤，N 4-苯甲酰基-胞嘧啶）开始制备13 C标记的核糖核苷（尿嘧啶和胸腺嘧啶）的总收率在47％至66％之间。它们随后转化为5'- O-二甲氧基三苯甲基保护的DNA-亚磷酰胺和5'- O-二甲氧基三苯甲基-2' - O-三烷基甲硅烷基保护的RNA-磷-酰胺，用于固相合成DNA-和RNA-低聚物，并转化为5' - Ø已经进行了用于模板控制的酶促合成（聚合酶-或逆转录酶反应）的-核糖核苷和-核糖核苷三磷酸。
• The first example of sequence-specific non-uniformly 13C5 labelled RNA: Synthesis of the 29mer HIV-1 TAR RNA with 13C Relaxation Window
  作者：Jan Milecki、Edouard Zamaratski、Tatiana V. Maltseva、András Földesi、Ryszard W. Adamiak、Jyoti Chattopadhyaya

  DOI：10.1016/s0040-4020(99)00294-x

  日期：1999.5

  A complete synthetic protocol as well as 1H- and 13C-NMR data on the monomer building blocks used for the solid-phase synthesis of specifically 13C-labelled (99 atom % 13C) stem (27A and 43G), bulge (24C) and loop (31U) regions of 29mer HIV-1 TAR RNA hairpin starting from the 13C6--glucose are presented. The complex NMR spectra of 13C-labelled monomer building blocks, due to the interaction of various

  完整的合成方案以及有关单体结构单元的1 H和13 C-NMR数据，这些单体用于固相合成13 C标记（99％原子的13 C）茎（27 A和43 G），凸起（24 C）和环（31 29聚体HIV-1 RNA TAR发夹U）区域从起始13 ç 6 - -葡萄糖被呈现。的复杂的NMR谱13 C标记的单体结构单元，由于各种的相互作用13 C和1已指定H个旋转。异核2D NMR已证明，通过化学合成在此处实现的HIV-1 TAR 29mer RNA的非均一标记提供了最佳的机会，可以进行完整的T 1和T 2弛豫测量（“ NMR弛豫窗口”）与统一标记的寡核苷酸RNA相比，由于13 C共振的最小重叠，所有四种策略性地将13 C标记的残基的糖碳的每种类型均以独特且前所未有的方式进行。