(2R,4R,5S,10R,11S,13R,20S)-7,11-dihydroxy-4-(hydroxymethyl)-20-methyl-7-oxo-3,6,8,26-tetraoxa-1,14,16,22-tetraza-7lambda5-phosphapentacyclo[18.3.1.12,5.110,13.114,18]heptacos-18(25)-ene-15,17,21,23-tetrone | 171755-06-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,4R,5S,10R,11S,13R,20S)-7,11-dihydroxy-4-(hydroxymethyl)-20-methyl-7-oxo-3,6,8,26-tetraoxa-1,14,16,22-tetraza-7lambda5-phosphapentacyclo[18.3.1.12,5.110,13.114,18]heptacos-18(25)-ene-15,17,21,23-tetrone
• 英文别名: (2R,4R,5S,10R,11S,13R,20S)-7,11-dihydroxy-4-(hydroxymethyl)-20-methyl-7-oxo-3,6,8,26-tetraoxa-1,14,16,22-tetraza-7λ5-phosphapentacyclo[18.3.1.12,5.110,13.114,18]heptacos-18(25)-ene-15,17,21,23-tetrone
• CAS: 171755-06-9
• 化学式: C₂₀H₂₇N₄O₁₂P
• 分子量: 546.428
• InChiKey: VCVUUXWYMPBUNV-OCJWLLHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.6
• 重原子数：
  37
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  214
• 氢给体数：
  5
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  胸苷酰(3'->5')胸苷铵盐 在 sodium dipicolinate 作用下， 生成 (2R,4R,5S,10R,11S,13R,20S)-7,11-dihydroxy-4-(hydroxymethyl)-20-methyl-7-oxo-3,6,8,26-tetraoxa-1,14,16,22-tetraza-7lambda5-phosphapentacyclo[18.3.1.12,5.110,13.114,18]heptacos-18(25)-ene-15,17,21,23-tetrone 、 SP TpT 、 、
  参考文献：
  名称：

  Combined NMR and DFT Studies for the Absolute Configuration Elucidation of the Spore Photoproduct, a UV-Induced DNA Lesion

  摘要：

  By irradiation of bacterial spores under UV radiation, a photoproduct (SP) bearing a covalent methylene link between two adjacent thymines is formed in DNA. Because of the presence of an asymmetric carbon on the aglycone and of two possible orientations for the formation of the cross-link, four isomers could in principle be obtained. Currently, no conclusive structural information of this photoproduct is available. The structure of the isolated SPTpT dinucleotide was revisited in order to determine the type of cross-link and the absolute configuration of the C-5a carbon. For this purpose, a study combining NMR spectroscopy and DFT calculations was pursued on the spore photoproduct of the dinucleoside TpT since its structure was previously shown to be identical to the one produced in DNA. A full characterization of SPTpT by NMR analyses was performed in D2O and DMSO. 2D NMR measurements (H-1-C-13, H-1-P-31, COSY, NOESY, and ROESY) and DFT calculations (geometries optimization of R and S isomers and theoretical chemical shifts) lead us to conclude without ambiguity that the absolute configuration of the C-5a. carbon is Rand that the methylene bridge of the photoproduct corresponds to the methyl group of the thymine located on the T-end of the dinucleoside monophosphate.

  DOI：

  10.1021/ja805032r