8-bromo-1-methyl-2'-deoxyguanosine

• 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-1-methyl-2'-deoxyguanosine
• 英文别名: N1-methyl-8-Br-dG；2-amino-8-bromo-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1-methylpurin-6-one
• 化学式: C₁₁H₁₄BrN₅O₄
• 分子量: 360.167
• InChiKey: IWWDHVRRLJNJTC-KVQBGUIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  126
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  8-bromo-1-methyl-2'-deoxyguanosine 、 4-羟基苯硼酸 在 palladium diacetate 、 trisodium tris(3-sulfophenyl)phosphine sodium carbonate 作用下， 以 水 、 乙腈 为溶剂， 反应 4.0h， 以23%的产率得到N1-methyl-8-(4-hydroxyphenyl)-2'-deoxyguanosine
  参考文献：
  名称：

  Biomarkers for Phenol Carcinogen Exposure Act as pH-Sensing Fluorescent Probes

  摘要：

  Biomarkers for phenolic carcinogen exposure, 8-(4' '-hydroxyphenyl)-2'-deoxypurines, have been found to possess pH-sensitive fluorescent properties. Phenolic ionization constants (pK(a)) establish substituent (sigma(-)) constants of 0.46 for N1-Me-dG and 0.55 for dA. Their fluorescent properties prompted the synthesis of 4 that possesses fluorescent pH sensing in the physiological pH region. Our results demonstrate the potential utility of these adducts for pH sensing within nucleic acids, as well as establishing a basis for phenol-mediated carcinogenesis.

  DOI：

  10.1021/ja068416l
• 作为产物：
  描述：

  N¹-methyl-2'-deoxyguanosine 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 水 为溶剂， 以71%的产率得到8-bromo-1-methyl-2'-deoxyguanosine
  参考文献：
  名称：

  Inhibitory Effects of the Guanine Moiety on Suzuki Couplings of Unprotected Halonucleosides in Aqueous Media

  摘要：

  In the Suzuki arylations of unprotected halonucleosides in aqueous media, 8-bromo-2'-deoxyguanosine (8BrdG) couplings were slower to reach completion than the corresponding 8-bromo-2'deoxyadenosine (8BrdA) couplings. The guanine moiety has an acidic proton, which under our Suzuki conditions (PH congruent to 10) may be deprotonated to give an anion that can coordinate to palladium. The possibility that guanine coordination was responsible for the observed slower rates was explored using additive experiments in which nonhalogenated nucleosides were added to the Suzuki coupling reaction of 8BrdA or 4-bromotoluene and PhB(OH)(2) and the reaction progress monitored by HPLC or GC. Adding dG slowed these reactions, and an induction period was observed. The addition of dA or 1-methyl-2'-deoxyguanosine (lMedG) to these couplings did not affect the rate of conversion to product. Guanine coordination was further explored using C-13 and P-31 NMR spectroscopy, which implies that guanine is coordinating to palladium through N-1 or O-6, or both. Furthermore, the presence of dG inhibited the formation of the active palladium(0) catalytic species, which may account for both the observed induction period and the sluggishness of reactions where guanine is involved.

  DOI：

  10.1021/jo050832l
• 作为试剂：
  描述：

  对溴甲苯 、 苯硼酸 在 palladium diacetate 8-bromo-1-methyl-2'-deoxyguanosine 、 trisodium tris(3-sulfophenyl)phosphine 、 sodium carbonate 作用下， 以 水 、 乙腈 为溶剂， 反应 2.0h， 生成 4-甲基联苯
  参考文献：
  名称：

  Inhibitory Effects of the Guanine Moiety on Suzuki Couplings of Unprotected Halonucleosides in Aqueous Media

  摘要：

  In the Suzuki arylations of unprotected halonucleosides in aqueous media, 8-bromo-2'-deoxyguanosine (8BrdG) couplings were slower to reach completion than the corresponding 8-bromo-2'deoxyadenosine (8BrdA) couplings. The guanine moiety has an acidic proton, which under our Suzuki conditions (PH congruent to 10) may be deprotonated to give an anion that can coordinate to palladium. The possibility that guanine coordination was responsible for the observed slower rates was explored using additive experiments in which nonhalogenated nucleosides were added to the Suzuki coupling reaction of 8BrdA or 4-bromotoluene and PhB(OH)(2) and the reaction progress monitored by HPLC or GC. Adding dG slowed these reactions, and an induction period was observed. The addition of dA or 1-methyl-2'-deoxyguanosine (lMedG) to these couplings did not affect the rate of conversion to product. Guanine coordination was further explored using C-13 and P-31 NMR spectroscopy, which implies that guanine is coordinating to palladium through N-1 or O-6, or both. Furthermore, the presence of dG inhibited the formation of the active palladium(0) catalytic species, which may account for both the observed induction period and the sluggishness of reactions where guanine is involved.

  DOI：

  10.1021/jo050832l