[1,3-15N2, 2-13C]-deoxyuridine

• 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: [1,3-15N2, 2-13C]-deoxyuridine
• 英文别名: 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl](213C,1,3-15N2)pyrimidine-2,4-dione
• 化学式: C₉H₁₂N₂O₅
• 分子量: 231.18
• InChiKey: MXHRCPNRJAMMIM-XPWHOUBVSA-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：
  0.56
• 拓扑面积：
  99.1
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [1,3-15N2, 2-13C]-deoxyuridine 在 咪唑 、 氢氟酸 作用下， 以 吡啶 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Enzymatic synthesis and RNA interference of nucleosides incorporating stable isotopes into a base moiety

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2015.09.011
• 作为产物：
  描述：

  2'-脱氧腺苷 在 purine nucleoside phosphorylase 、 thymidine phosphorylase 、 磷酸 作用下， 以 aq. phosphate buffer 为溶剂， 反应 50.0h， 生成 [1,3-15N2, 2-13C]-deoxyuridine
  参考文献：
  名称：

  ヌクレオシド化合物の製造方法

  摘要：

  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。

  公开号：

  JP2015160832A

文献信息

• 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.
• 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。