8-bromo-2'-deoxy-3',5'-di-O-acetylguanosine | 879998-59-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 8-bromo-2'-deoxy-3',5'-di-O-acetylguanosine
• 英文别名: [(2R,3S,5R)-3-acetyloxy-5-(2-amino-8-bromo-6-oxo-1H-purin-9-yl)oxolan-2-yl]methyl acetate
• CAS: 879998-59-1
• 化学式: C₁₄H₁₆BrN₅O₆
• 分子量: 430.215
• InChiKey: ORXFHNYCEDGOJL-DJLDLDEBSA-N

物化性质

• 沸点：
  642.9±65.0 °C(Predicted)
• 密度：
  1.98±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  147
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  四(三苯基膦)钯 、 8-bromo-2'-deoxy-3',5'-di-O-acetylguanosine 以 四氢呋喃 为溶剂， 反应 12.0h， 以74%的产率得到
  参考文献：
  名称：

  嘌呤核苷通过氧化加成的选择性C8金属化

  摘要：

  8-溴-2'-脱氧-3'，5'-二-O-乙酰鸟嘌呤（1），8-溴-2'，3'，5'-三-O-乙酰鸟嘌呤（2），8-溴- 2′-脱氧-3′，5′-二-O-乙酰腺苷（3）和8-溴-2′，3′，5′-三-O-乙酰腺苷（4）与[Pd（PPh 3）反应4 ]通过C8-Br氧化加成反应生成C8 palpalated的氮杂络合物[ 5 ]-[ 8 ]，其特征是未质子化的N7环氮原子。该配合物具有非对位转位的三苯基膦配体，可测定2 J PP反式-[PdL 2（PPh 3）2 ]类型的络合物（[ 7 ]的2 J PP = 442 Hz ）。此外，[ 7 ]的两个复杂分子以固态形式形成反式Watson-Crick / Hoogsteen AA碱基对。用三氟甲磺酸lut啶鎓对鸟嘌呤衍生的复合物[ 5 ]和[ 6 ]与HBF 4 ·Et 2 O和腺苷衍生的复合物[ 7 ]和[ 8 ]进行N7质子化反应，生成复合物[

  DOI：

  10.1021/acs.organomet.8b00685
• 作为产物：
  描述：

  3',5'-di-O-acetyl-8-oxo-7,8-dihydro-2'-deoxyguanosine 在 溴 作用下， 以 水 为溶剂， 生成 8-bromo-2'-deoxy-3',5'-di-O-acetylguanosine
  参考文献：
  名称：

  Reaction of 3′,5′-di-O-acetyl-2′-deoxyguansoine with hypobromous acid

  摘要：

  Hypobromous acid (HOBr) is formed by eosinophil peroxidase and myeloperoxidase in the presence of H2O2, Cl-, and Br- in the host defense system of humans, protecting against invading bacteria. However, the formed HOBr may cause damage to DNA and its components in the host. When a guanine nucleoside (3',5'-di-O-acetyl-2'-deoxyguansoine) was treated with HOBr at pH 7.4, spiroiminodihydantoin, guanidinohydantoin/iminoallantoin, dehydro-iminoallantoin, diimino-imidazole, amino-imidazolone, and diamino-oxazolone nucleosides were generated in addition to an 8-bromoguanine nucleoside. The major products were spiroiminodihydantoin under neutral conditions and guanidinohydantoin/iminoallantoin under mildly acidic conditions. All the products were formed in the reaction with HOCl in the presence of Br-. These products were also produced by eosinophil peroxidase or myeloperoxidase in the presence of H2O2, Cl-, and B-. The results suggest that the products other than 8-bromoguanine may also have importance for mutagenesis by the reaction of HOBr with guanine residues in nucleotides and DNA. (C) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.04.060

文献信息

• Practical Halogenations of Nucleosides Using Tetrabutylammonium Peroxydisulfate
  作者：Yong Hae Kim、Hee Yoon Lee、Vasu Sampath、Vidyadhar Jadhav

  DOI：10.3987/com-05-s(k)13

  日期：——