3-(3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-8-hydroxy-6-methyl-5,6,7,8-tetrahydro-3H-1,3,4,5,8a-pentaaza-cyclopenta[b]naphthalen-9-one

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 3-(3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-8-hydroxy-6-methyl-5,6,7,8-tetrahydro-3H-1,3,4,5,8a-pentaaza-cyclopenta[b]naphthalen-9-one
• 英文别名: 3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-8-hydroxy-6-methyl-5,6,7,8-tetrahydropyrimido[1,2-a]purin-10-one
• 化学式: C₁₄H₁₉N₅O₆
• 分子量: 353.335
• InChiKey: LVHPHBKWMWGZLO-HZPYULPISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  153
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-(3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-8-hydroxy-6-methyl-5,6,7,8-tetrahydro-3H-1,3,4,5,8a-pentaaza-cyclopenta[b]naphthalen-9-one 生成
  参考文献：
  名称：

  Cross-Link Dimer Formation of the Acetaldehyde-Derived Cyclic 1,N2-Propano-2'-deoxyguanosine Adduct Using Electrochemical Oxidation

  摘要：

  2′-deoxyguanosine 1 的乙醛衍生环丙酸加合物 2 的电化学氧化损伤被确定为加合物 2 的交联二聚体 4。交联形成的原因是 2 中的外环氨基对通过 1 个质子和 2 个电子转移产生的碳位 3 具有亲核偏好。在双链 DNA 暴露于乙醛后进行电化学氧化的过程中，也检测到了二聚体的形成。据推断，这种二聚体是在双链 DNA 的 G-G 序列中特别生成的链内交联，预计它是乙醛介导的基因毒性的原因之一。

  DOI：

  10.1248/cpb.57.1434
• 作为产物：
  描述：

  鸟苷 、 丁烯-2-醛 在 phosphate buffer 、 L-精氨酸 作用下， 反应 2.0h， 以90%的产率得到3-(3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-8-hydroxy-6-methyl-5,6,7,8-tetrahydro-3H-1,3,4,5,8a-pentaaza-cyclopenta[b]naphthalen-9-one
  参考文献：
  名称：

  A convenient preparative method for the 1,N2-cyclic adducts of guanine nucleosides and nucleotides with crotonaldehyde

  摘要：

  The treatment of guanine nucleosides and nucleotides with excess crotonaldehyde in pH 8.0 phosphate buffer containing an equimolar amount of L-arginine at 50degreesC for 2 h resulted in the selective formation of the corresponding cyclic 1,N-2 -propano adducts as a mixture of its diastercomers. 0 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01047-5

文献信息

• A convenient preparative method for the 1,N2-cyclic adducts of guanine nucleosides and nucleotides with crotonaldehyde
  作者：Magoichi Sako、Isamu Yaekura

  DOI：10.1016/s0040-4020(02)01047-5

  日期：2002.10

  The treatment of guanine nucleosides and nucleotides with excess crotonaldehyde in pH 8.0 phosphate buffer containing an equimolar amount of L-arginine at 50degreesC for 2 h resulted in the selective formation of the corresponding cyclic 1,N-2 -propano adducts as a mixture of its diastercomers. 0 2002 Elsevier Science Ltd. All rights reserved.
• Cross-Link Dimer Formation of the Acetaldehyde-Derived Cyclic 1,N2-Propano-2'-deoxyguanosine Adduct Using Electrochemical Oxidation
  作者：Hiroya Murakami、Yukihiro Esaka、Bunji Uno

  DOI：10.1248/cpb.57.1434

  日期：——

  The electrochemically oxidative lesion of the acetaldehyde-derived cyclic propano adduct 2 of 2′-deoxyguanosine 1 was identified as the cross-linked dimer 4 of adduct 2. Cross-link formation is explained by the nucleophilic preference of the exocyclic amino group in 2 to the carbocation 3 electrogenerated by 1-proton and 2-electron transfers. Dimer formation was also detected in duplex DNA during exposure to acetaldehyde followed by electrochemical oxidation. The dimer has been deduced to be an intrastrand cross-link generated specifically in the G–G sequence in duplex DNA, which is expected to contribute to acetaldehyde-mediated genotoxicity.

  2′-deoxyguanosine 1 的乙醛衍生环丙酸加合物 2 的电化学氧化损伤被确定为加合物 2 的交联二聚体 4。交联形成的原因是 2 中的外环氨基对通过 1 个质子和 2 个电子转移产生的碳位 3 具有亲核偏好。在双链 DNA 暴露于乙醛后进行电化学氧化的过程中，也检测到了二聚体的形成。据推断，这种二聚体是在双链 DNA 的 G-G 序列中特别生成的链内交联，预计它是乙醛介导的基因毒性的原因之一。