N²-Benzyl-2'-deoxyguanosine | 208597-31-3

• 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: N²-Benzyl-2'-deoxyguanosine
• 英文别名: n2-Benzyl-2'-deoxyguanosine；2-(benzylamino)-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-6-one
• CAS: 208597-31-3
• 化学式: C₁₇H₁₉N₅O₄
• 分子量: 357.369
• InChiKey: OFBJAGLROLWMEV-YNEHKIRRSA-N

物化性质

• 密度：
  1.62±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  121
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N²-Benzyl-2'-deoxyguanosine 在 盐酸 作用下， 生成 N2-Benzylguanin
  参考文献：
  名称：

  {}N-Nitrosobenzylmethylamine Is Activated to a DNA Benzylating Agent in Rats

  摘要：

  The ability of rat tissues to activate the esophageal carcinogen, N-nitrosobenzylmethylamine (NBzMA), to a DNA benzylating intermediate was investigated. [3-H-3]NBzMA was prepared and given to male F344 rats. Tissues were harvested 4 h after treatment, and DNA was isolated. HPLC analysis with radiochemical detection of chemical and enzymatic hydrolysates of DNA from liver and lung revealed the formation of benzyl adducts. Benzyl alcohol, N-2-benzylguanine, 3-benzyladenine, N-6-benzyladenine, and 7-benzylguanine were the major radioactive components in the hydrolysates. An unknown adduct was also observed. The adduct distribution was similar to that observed in [3-H-3]benzylnitrosourea ([3-H-3]BzNU)treated calf thymus DNA. However, enzymatic hydrolysates of [3-H-3]BzNU-treated DNA also contained significant levels of O-6-benzyl-2'-deoxyguanosine (O-6-BzdG). This radioactive adduct disappeared upon incubation of the DNA with a crude preparation of the repair protein, O-6-alkylguanine-DNA alkyltransferase isolated from rat liver. These data provide evidence that O-6-BzdG is probably rapidly repaired in vivo. No benzylation of esophageal mucosal DNA was detected. The level of DNA benzylation observed in tissues from [3-H-3]NBzMA-treated rats was several orders of magnitude lower than the level of DNA methylation in these same tissues. Therefore, these data indicate that DNA benzylation plays a minor role, if any, in the carcinogenic activity of NBzMA.

  DOI：

  10.1021/tx9601014
• 作为产物：
  描述：

  5'-O-3'-O-bis(tert-butyldimethylsilyl)-6-O-benzyl-2-N-benzyl-2'-deoxyguanosine 在 palladium on activated charcoal 氢气 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 N²-Benzyl-2'-deoxyguanosine
  参考文献：
  名称：

  Synthesis of biologically active N2-amine adducts of 2′-deoxyguanosine

  摘要：

  Several biologically important N-2-adducts of 2'-deoxyguanosine (dG) that previously were difficultly accessible, have been synthesized directly by means of the Buchwald-Hartwig reaction. The reaction employed in each case involves the coupling of 2'-deoxy-2-bromoinosine with the appropriate amine. Deprotection in all cases gave good yields of the desired 2-alkylated or -arylated deoxynucleoside. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01196-5

文献信息

• Effect of Ionic State of 2‘-Deoxyguanosine and Solvent on Its Aralkylation by Benzyl Bromide
  作者：Ki-Young Moon、Robert C. Moschel

  DOI：10.1021/tx980012m

  日期：1998.6.1

  To extend studies of the aralkylation of nucleic acid components under a variety of solvent conditions, we determined product distributions from the reactions of benzyl bromide with 2'-deoxyguanosine and the anion of 2'-deoxyguanosine in 2,2,2-trifluoroethanol (TFE) and compared these distributions with those from the reaction of the anion with benzyl bromide in N'\N-dimethylacetamide (DMA). 7-Benzylguanine was the only benzylated product detected in the reaction with the neutral nucleoside in TFE, In striking contrast, the reaction of the anion of 2'-deoxyguanosine with benzyl bromide in TFE produced N-2-benzyl-2'-deoxyguanasine in significant yield and with high selectivity. The reaction of the anion of 2'-deoxyguanosine with benzyl bromide in DMA produced products derived only from reaction at the 1- and/or 7-position of the nucleoside. The weakly nucleophilic but protic polar solvent TFE and the iminolate tautomeric form of the 2'-deoxyguanosine anion appear to be essential for benzylation at the exocyclic N-2-position.
• BORANE-AMINE COMPLEXES - VERSATILE REAGENTS IN THE CHEMISTRY OF NUCLEIC ACIDS AND THEIR ANALOGS
  作者：Zinaida A. Sergueeva、Dmitri S. Sergueev、Barbara Ramsay Shaw

  DOI：10.1081/ncn-100002464

  日期：2001.3.31

  A new method for synthesis of N-alkylated nucleosides was developed. Exceptionally mild and selective conversion of N-acyl to the corresponding N-alkyl nucleosides was achieved by reduction with borane-amine complexes. The borane-amine complexes were also used as efficient scavengers of a 4,4'-dimethoxytrityl (DMT) cation. Neutralization of the cation eliminated the boranophosphate group degradation during acidic DMT deprotection and allowed milder acidic conditions for the deprotection.