2,4(1H,3H)-嘧啶二酮-2-13C-1,3-15N2 | 181517-11-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 2,4(1H,3H)-嘧啶二酮-2-13C-1,3-15N2
• 中文别名: 尿嘧啶-2-13C,15N2
• 英文名称: [2-13C,15N2]uracil
• 英文别名: [1,3-15N2, 2-13C]-uracil；Uracil-13C,15N2；(213C,1,3-15N2)1H-pyrimidine-2,4-dione
• CAS: 181517-11-3
• 化学式: C₄H₄N₂O₂
• 分子量: 115.064
• InChiKey: ISAKRJDGNUQOIC-VMGGCIAMSA-N

物化性质

• 熔点：
  >300 °C (lit.)
• 溶解度：
  DMSO：可溶，甲醇：水（1:1）：可溶

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 安全说明：
  S22,S24/25

反应信息

• 作为反应物：
  描述：

  2,4(1H,3H)-嘧啶二酮-2-13C-1,3-15N2 在 溴 、 溶剂黄146 作用下， 反应 0.5h， 生成 5-bromouracil-[1,3-15N2-2-13C]
  参考文献：
  名称：

  Synthesis of isotopically labelled DNA degradation products for use in mass spectrometric studies of cellular DNA damage

  摘要：

  Thirteen substituted purines and pyrimidines bearing from three to five carbon, nitrogen and/or deuterium isotopic labels have been synthesized in yields ranging from .1 to 70%. Most of the products originate from the same small number of commercially available labelled starting materials, and in several cases one intermediate leads to two products, thus minimizing the expense and time required. The parent compounds are found in tissue as the result of DNA damage often linked with carcinogenesis and mutagenesis. The synthesized compounds serve as internal standards for the study of DNA damage using mass spectrometry.

  DOI：

  10.1002/(sici)1099-1344(199608)38:8<713::aid-jlcr886>3.0.co;2-i
• 作为产物：
  描述：

  脲-13C,15N2 、 丙炔酸 以 苯 为溶剂， 反应 40.0h， 以1.01 g的产率得到2,4(1H,3H)-嘧啶二酮-2-13C-1,3-15N2
  参考文献：
  名称：

  一种双标记尿嘧啶核苷-(13C ,15N2)的合成方 法

  摘要：

  本发明涉及一种双标记尿嘧啶核苷‑( 13 C, 15 N 2 )的合成方法，该方法以无水苯为溶剂，双标记尿素‑( 13 C, 15 N 2 )和丙炔酸为原料进行环化反应，得到双标记尿嘧啶‑( 13 C, 15 N 2 )；在Ar 2 气氛下，乙腈作溶剂，双标记尿嘧啶‑( 13 C, 15 N 2 )和1‑乙酰氧基‑2,3,5‑三苯甲酰氧基‑β‑D‑呋喃核糖混合，接着加入六甲基二硅氮烷和三氟甲基磺酸三甲基硅脂，经后处理后得到的中间体用氨水水解，即可得到双标记尿嘧啶核苷‑( 13 C, 15 N 2 )。与现有技术相比，本发明工艺简单，收率较高，同位素丰度不下降，适合实验室生产双标记尿嘧啶核苷‑( 13 C, 15 N 2 )。

  公开号：

  CN106397514B

文献信息

• Transglycosylation in the Modification and Isotope Labeling of Pyrimidine Nucleosides
  作者：Yong Gong、Lu Chen、Wei Zhang、Rhys Salter

  DOI：10.1021/acs.orglett.0c01941

  日期：2020.7.17

  Transglycosylation of pyrimidine nucleosides is demonstrated in a one-pot synthesis of uridine derivatives under microwave irradiation. Inductive activation of 2′,3′,5′-tri-O-acetyl uridine with a 5-nitro group produces a more-reactive glycosyl donor. Under optimized Vorbrüggen conditions, the 5-nitrouridine facilitates a reversible nucleobase exchange with a series of 5-substituted uracils. The protocol

  嘧啶核苷的转糖基化在微波辐射下一锅合成尿苷衍生物中得到证明。具有5-硝基的2'，3'，5'-三-O-乙酰尿苷的感应活化产生反应性更高的糖基供体。在优化的Vorbrüggen条件下，5-硝基尿苷促进了与一系列5-取代的尿嘧啶的可逆核碱基交换。该协议还以热加热下的克级反应为例。该策略可轻松获得同位素标记的尿苷。
• ヌクレオシド化合物の製造方法
  申请人：大陽日酸株式会社

  公开号：JP2015160832A

  公开（公告）日：2015-09-07

  【課題】同位体標識されたヌクレオシド化合物を効率的に製造することができるヌクレオシド化合物の製造方法の提供。【解決手段】原材料ヌクレオシド化合物と、塩基とを、リン酸イオンを含む水溶液中において、ヌクレオシドホスホリラーゼにより塩基交換反応させて、目的ヌクレオシド化合物を得る工程を含み、前記目的ヌクレオシド化合物が安定同位体標識又は放射性同位体標識されたものであることを特徴とするヌクレオシド化合物の製造方法。【選択図】なし

  提供一种可以高效制备同位素标记的核苷化合物的方法。通过在含有磷酸根离子的水溶液中，让原料核苷化合物与碱基经由核苷酸磷酸化酶进行碱基交换反应，从而得到目标核苷化合物的步骤。其中，所述目标核苷化合物是稳定同位素标记或放射性同位素标记的。
• Nitro-Activated Nucleobase Exchange in the Synthesis of 2′-Fluoro-2′-Deoxyribonucleosides
  作者：Yong Gong、Wei Zhang、Lu Chen、Ronghui Lin、Ronghui Zhou、Rhys Salter

  DOI：10.1021/acs.joc.2c01093

  日期：2022.7.15

  Functionalized nucleosides bearing pyrimidine or purine bases can be prepared by activation of accessible pyrimidine nucleosides and subsequent transglycosylation. Nitration of lumicitabine, a 2′-fluoro-2′-deoxycytidine class antiviral agent, and its 2′-fluoro-2′-deoxyuridine precursor produce the same 5-nitro-2′-fluoro-2′-deoxyuridine. Under Vorbrüggen conditions, 5-nitrouracil serves as the leaving

  带有嘧啶或嘌呤碱基的功能化核苷可以通过活化可接近的嘧啶核苷和随后的转糖基化来制备。lumicitabine（一种 2'-fluoro-2'-deoxycytidine 类抗病毒剂）及其 2'-fluoro-2'-deoxyuridine 前体的硝化产生相同的 5-nitro-2'-fluoro-2'-deoxyuridine。在 Vorbrüggen 条件下，5-硝基尿嘧啶作为离去核碱基，能够与嘧啶和嘌呤核碱基交换为异头 2'-氟-2'-脱氧核糖核苷，通常有利于 β-端基异构体。该策略也适用于 2'-fluoro-2'-deoxyuridines 的同位素标记。
• Simultaneous Determination of Five Oxidative DNA Lesions in Human Urine
  作者：Jean-Luc Ravanat、Pascale Guicherd、Zorana Tuce、Jean Cadet

  DOI：10.1021/tx980194k

  日期：1999.9.1

  A method, involving a HPLC prepurification followed by a GC/MS analysis, has been set up for the measurement of nucleic acid oxidation products in human urine. For this purpose, isotopically labeled internal standards have been prepared and used for isotope dilution mass spectrometric detection. Using this approach, four oxidized DNA bases, i.e., 5-hydroxyuracil, 5-(hydroxymethyl)uracil, 8-oxo-7,8-dihydroadenine, and 8-oxo-7,8-dihydroguanine, together with 8-oxo-7,8-dihydro-2'-deoxyguanosine have been simultaneously quantified in human urine samples. The levels of the oxidized nucleic acid constituents, as expressed in picomoles per milliliter, were determined to be, in decreasing order: 8-oxo-7,8-dihydroguanine (583 +/- 376) > 5-(hydroxymethyl)uracil (121 +/- 56) > 5-hydroxyuracil (58 +/- 23) > 8-oxo-7,8-dihydro-2'-deoxyguanosine (30 +/- 15) > 8-oxo-7,8-dihydroadenine (7 +/- 4). Attempts to determine the amount of 5,6-dihydroxy-5,6-dihydrothymine, 5-hydroxycytosine, and 2,6-diamino-4-hydroxy-5-formamidopyrimidine using the above HPLC-GC/MS method were unsuccessful.
• Enzymatic synthesis and RNA interference of nucleosides incorporating stable isotopes into a base moiety
  作者：Akihiko Hatano、Mitsuya Shiraishi、Nanae Terado、Atsuhiro Tanabe、Kenji Fukuda

  DOI：10.1016/j.bmc.2015.09.011

  日期：2015.10

  Thymidine phosphorylase was used to catalyze the conversion of thymidine (or methyluridine) and uracil incorporating stable isotopes to deoxyuridine (or uridine) with the uracil base incorporating the stable isotope. These base-exchange reactions proceeded with high conversion rates (75-96%), and the isolated yields were also good (64-87%). The masses of all synthetic compounds incorporating stable isotopes were identical to the theoretical molecular weights via EIMS. C-13 NMR spectra showed spin-spin coupling between C-13 and N-15 in the synthetic compounds, and the signals were split, further proving incorporation of the isotopes into the compounds. The RNA interference effects of this siRNA with uridine incorporating stable isotopes were also investigated. A 25mer siRNA had a strong knockdown effect on the MARCKS protein. The insertion position and number of uridine moieties incorporating stable isotopes introduced into the siRNA had no influence on the silencing of the target protein. This incorporation of stable isotopes into RNA and DNA has the potential to function as a chemically benign tracer in cells. (c) 2015 Elsevier Ltd. All rights reserved.