hexahydro-cyclobuta[1,2-d;4,3-d']dipyrimidine-2,4,5,7-tetraone | 13375-99-0

• 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: hexahydro-cyclobuta[1,2-d;4,3-d']dipyrimidine-2,4,5,7-tetraone
• 英文别名: (4aalpha,4balpha,8aalpha,8balpha)-4a,4b,8a,8b-Tetrahydrocyclobuta[1,2-d:4,3-d/']dipyrimidine-2,4,5,7(1H,3H,6H,8H)-te；(1R,2S,7S,8R)-3,5,10,12-tetrazatricyclo[6.4.0.02,7]dodecane-4,6,9,11-tetrone
• CAS: 13375-99-0
• 化学式: C₈H₈N₄O₄
• 分子量: 224.176
• InChiKey: XFDCFFIAUVAAFU-GNSDDBTRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  hexahydro-cyclobuta[1,2-d;4,3-d']dipyrimidine-2,4,5,7-tetraone 在 盐酸 作用下， 以 水 为溶剂， 生成 6-(4'-Pyrimidin-2'-on)uracil
  参考文献：
  名称：

  尿嘧啶的光化学：重新研究。

  摘要：

  呈现了对尿嘧啶（Ura）经历的光化学反应进行重新检查的结果。在-78.5摄氏度的冷冻水溶液中照射Ura会产生两种非对映异构（6-4）产物，即5-羟基-6-4'-（嘧啶-2'-一）-5,6的顺式和反式异构体-二氢尿嘧啶。在0.1m HCl中加热后，这些化合物各自分解形成6-4'-（嘧啶-2'-one）尿嘧啶。另外，提供了产生Ura三聚体的水合物的证据，该化合物在254nm处的辐射形成Ura和作为产物的（6-4）加合物。在冷冻水溶液中照射Ura后，还存在化合物5-4'-（嘧啶-2'-一）尿嘧啶和6-羟基-5,6-二氢尿嘧啶。当在冷冻的水性状态下照射Ura时，会形成环丁烷二聚体（CBD），在液体水溶液和乙腈溶液中，并在有光敏剂（例如丙酮）的情况下使用。关于在这些光化学系统中形成的四个CBD异构体（顺式，顺式，反式，反式和反式）的身份和相对定量重要性的公开信息并不完整，而且常常存在分歧。使用化学方

  DOI：

  10.1111/j.1751-1097.2010.00826.x
• 作为产物：
  描述：

  在 盐酸 、 水 作用下， 反应 0.5h， 生成 hexahydro-cyclobuta[1,2-d;4,3-d']dipyrimidine-2,4,5,7-tetraone
  参考文献：
  名称：

  Synthesis, Crystal Structure, and Enzymatic Evaluation of a DNA-Photolesion Isostere

  摘要：

  Nucleotide analogues are useful tools for the investigation of interactions between DNA-binding proteins and DNA at a molecular level. Herein we describe the synthesis of the DNA-lesion analogue 2, which is required to determine the extent to which specific phosphodiesters in the DNA backbone contribute to the recognition of cyclobutane pyrimidine dimer DNA lesion by the dimer-specific repair enzymes DNA photolyases or T4-endonuclease V. The analogue 2 is a close structural mimic of cyclobutane pyrimidine dimers like 1. which are the major lesions induced upon irradiation of cells with UV light. Instead of the negatively charged phosphate link in 1, analogue 2 contains an uncharged but isosteric formacetal moiety. The analysis of this and other phosphodiester contacts is hoped to provide insight into the lesion recognition process, which is currently believed to require the nipping of the lesioned base out of the DNA double helix. The lesion analogue 2 is synthetically available in large quantities, which allowed us to establish a new, fast and sensitive DNA photolyase assay. A precise X-ray crystal structure analysis of the DNA-lesion analogue 2 is also presented. The structure underlines the isosteric character of 2 and reveals, in combination with the only other available X-ray crystal structure determined from a thymine-dimer triester analogue, interesting structural features of cyclobutane pyrimidine dimer lesions. We describe the incorporation of the lesion analogue 2 into oligonucleotides by using standard phosphoramidite chemistry. Initial enzymatic repair studies are reported with three different types of DNA photolyases. These studies show that the lesion analogue 2 is rapidly repaired by photolyases from Anacystis nidulans, Neurospora crassa and from the marsupial Potorous tridactylis. The enzymatic investigations indicate that all photolyases, including enzymes from higher organisms (Tridactylis) accept the formacetal dimer as a lesion substrate and therefore could possess a similar DNA-lesion recognition process, in which the interaction with the central phosphate unit is only of limited importance.

  DOI：

  10.1002/(sici)1521-3765(19980416)4:4<642::aid-chem642>3.0.co;2-k

文献信息

• Dobos, S.; Fidy, J.; Laczko, Zs., Acta Chimica Academiae Scientiarum Hungaricae, 1981, vol. 106, # 1, p. 17 - 30
  作者：Dobos, S.、Fidy, J.、Laczko, Zs.

  DOI：——

  日期：——