<5-¹⁵N>-5,6-diamino-2-thioxo-1,2-dihydro-4(3H)-pyrimidinone | 173170-77-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: <5-¹⁵N>-5,6-diamino-2-thioxo-1,2-dihydro-4(3H)-pyrimidinone
• 英文别名: 6-amino-5-(15N)azanyl-2-sulfanylidene-1H-pyrimidin-4-one
• CAS: 173170-77-9
• 化学式: C₄H₆N₄OS
• 分子量: 159.177
• InChiKey: QYSWOQHLIDKEOL-HOSYLAQJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  10
• 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：
  125
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  <5-¹⁵N>-5,6-diamino-2-thioxo-1,2-dihydro-4(3H)-pyrimidinone 在 ammonium hydroxide 、 镍 作用下， 反应 2.5h， 以99%的产率得到<5-¹⁵N>-5,6-diamino-4(3H)-pyrimidinone
  参考文献：
  名称：

  The synthesis of 15 N(7)-Hoogsteen face-labeled adenosine phosphoramidite for solid-phase RNA synthesis

  摘要：

  AbstractWe have developed an efficient route for the synthesis of 15N(7)-labeled adenosine as phosphoramidite building block for site- and atom-specific incorporation into RNA by automated solid-phase synthesis. Such labeled RNA is required for the evaluation of selected non-canonical base pair interactions in folded RNA using NMR spectroscopic methods. Graphical abstract

  DOI：

  10.1007/s00706-016-1882-8
• 作为产物：
  描述：

  <5-¹⁵N>-6-amino-5-nitroso-2-thioxo-1,2-dihydro-4(3H)-pyrimidinone 在 碳酸氢钠 、 sodium sulfate 作用下， 以 水 为溶剂， 反应 7.0h， 以95%的产率得到<5-¹⁵N>-5,6-diamino-2-thioxo-1,2-dihydro-4(3H)-pyrimidinone
  参考文献：
  名称：

  The synthesis of 15 N(7)-Hoogsteen face-labeled adenosine phosphoramidite for solid-phase RNA synthesis

  摘要：

  AbstractWe have developed an efficient route for the synthesis of 15N(7)-labeled adenosine as phosphoramidite building block for site- and atom-specific incorporation into RNA by automated solid-phase synthesis. Such labeled RNA is required for the evaluation of selected non-canonical base pair interactions in folded RNA using NMR spectroscopic methods. Graphical abstract

  DOI：

  10.1007/s00706-016-1882-8

文献信息

• Syntheses of [6,7-15N]-Adenosine, [6,7-15N]-2'-Deoxyadenosine, and [7-15N]-Hypoxanthine
  作者：Alex R. Pagano、Wayne M. Lajewski、Roger A. Jones

  DOI：10.1021/ja00152a006

  日期：1995.11

  We have developed a high-yield route for the synthesis of [7-N-15]-hypoxanthine in four steps in an overall yield of 81%. This procedure uses [N-15]-sodium nitrite as the N-15 source and an inexpensive pyrimidine to provide an economical route to this useful N-15-labeled intermediate. Conversion to [7-N-15]-6-chloropurine followed by enzymatic transglycosylation gives the corresponding ribo- and 2'-deoxyribonucleosides. Ammonolysis of the 6-chloro moiety to give the [6,7-N-15]-labeled nucleosides is effected simply and in high yield using 2 equiv of [N-15]-ammonium chloride and 3 equiv of potassium bicarbonate.
• Use of ¹³C as an Indirect Tag in ¹⁵N Specifically Labeled Nucleosides. Syntheses of [8-¹³C-1,7,NH₂-¹⁵N₃]Adenosine, -Guanosine, and Their Deoxy Analogues
  作者：Anthony J. Shallop、Barbara L. Gaffney、Roger A. Jones

  DOI：10.1021/jo0345446

  日期：2003.10.1

  We have previously reported the use of a C-13 tag at the C2 of N-15-multilabeled purine nucleosides to distinguish the adjacent-labeled N-15 atoms from those in an untagged nucleoside. We now introduce the use of an indirect tag at the C8 of (15)N7-labeled purine nucleosides. This tag allows unambiguous differentiation between a pair of (15)N7-labeled purines in which only one is (13)C8 labeled. Although the very small C8-N7 coupling (< 1 Hz) precludes its direct detection in 1D N-15 spectra, 2D H-1-N-15 NMR experiments display the large C8-H8 coupling (>200 Hz) because H8 is coupled to both N7 and C8. The (13)C8 atom is introduced by means of a ring closure of the exocyclic amino groups of a pyrimidinone using [C-13] sodium ethyl xanthate. Here, we present methods for the syntheses of [8-C-13-1,7,NH2- N-15(3)]adenosine, -guanosine, and their deoxy analogues.