8-溴-9-(2-脱氧呋喃戊糖基)-2-{(E)-[(二甲基氨基)亚甲基]氨基}-1,9-二氢-6H-嘌呤-6-酮 | 717876-75-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 中文名称: 8-溴-9-(2-脱氧呋喃戊糖基)-2-{(E)-[(二甲基氨基)亚甲基]氨基}-1,9-二氢-6H-嘌呤-6-酮
• 英文名称: 8-Bromo-2'-deoxy-N-[(dimethylamino)methylidene]guanosine
• 英文别名: N'-[8-bromo-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-oxo-1H-purin-2-yl]-N,N-dimethylmethanimidamide
• CAS: 717876-75-0
• 化学式: C₁₃H₁₇BrN₆O₄
• 分子量: 401.22
• InChiKey: ZSILXQZBZDBZNX-XLPZGREQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  125
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  8-溴-9-(2-脱氧呋喃戊糖基)-2-{(E)-[(二甲基氨基)亚甲基]氨基}-1,9-二氢-6H-嘌呤-6-酮 在 四(三苯基膦)钯 吡啶 、 4-二甲氨基吡啶 、 copper(l) iodide 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 N(2)-dimethylaminomethylene-8-(prop-1-ynyl)-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyguanosine
  参考文献：
  名称：

  DNA duplexes stabilized by modified monomer residues: synthesis and stability

  摘要：

  本文描述了一系列在 5 位修饰的 2′-脱氧尿苷类似物和一系列在 8 位修饰的 2′-脱氧尿苷的合成过程。紫外线熔解研究被用来评估含有这些修饰的 12 位和 8 位 DNA 双链的稳定性。热力学分析表明，稳定性增加的原因是与 DNA 碱基堆叠过程有关的焓的降低。我们认为丙炔分子的稳定程度可能与序列有关。

  DOI：

  10.1039/a707031d
• 作为产物：
  描述：

  8-溴-2'-脱氧鸟苷 、 N,N-二甲基甲酰胺二乙基缩醛 以 甲醇 为溶剂， 反应 6.0h， 以100%的产率得到8-溴-9-(2-脱氧呋喃戊糖基)-2-{(E)-[(二甲基氨基)亚甲基]氨基}-1,9-二氢-6H-嘌呤-6-酮
  参考文献：
  名称：

  Synthesis of novel push–pull-type solvatochromic 2′-deoxyguanosine derivatives with longer wavelength emission

  摘要：

  We synthesized novel push-pull-type fluorescent guanosine derivatives, (CN)G and (Ac)G containing 1,6- and 2,7-disubstituted pyrene chromophores. 1,6-Disubstituted pyrene derivatives, 1,6-(CN)G (3b) and 1,6-(Ac)G (3c), exhibited highly solvatochromic fluorescence emission at longer wavelength (similar to 540 nm). The environmentally sensitive fluorescent deoxyguanosines such as 3b and 3c can be used as powerful tools for structural studies of nucleic acids and molecular diagnostics. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.03.012

文献信息

• SYNTHESIS AND PROPERTIES OF OLIGONUCLEOTIDES CONTAINING 8-BROMO-2′-DEOXYGUANOSINE
  作者：Carme Fàbrega、Maria J. Macías、Ramon Eritja

  DOI：10.1081/ncn-100002085

  日期：2001.2.28

  The preparation of oligonucleotides containing 8-bromo-2′-deoxyguanosine is described. Substitution of G by 8-bromoguanine on an alternating CG decamer stabilizes the Z-form in such a way that the B-form was not observed. Melting temperatures showed that duplexes in which 8-bromo-2′-deoxyguanosine paired with natural bases were much less stable.

  描述了含有8-溴-2'-脱氧鸟苷的寡核苷酸的制备。在交替的CG decamer上用8-溴鸟嘌呤取代G可以稳定Z形式，使得未观察到B形式。熔融温度表明，其中8-溴-2'-脱氧鸟苷与天然碱基配对的双链体的稳定性要差得多。
• Fluorescence switching of photochromic vinylpyrene-substituted 2′-deoxyguanosine
  作者：Yoshio Saito、Katsuhiko Matsumoto、Yoshiki Takeuchi、Subhendu Sekhar Bag、Satoshi Kodate、Takashi Morii、Isao Saito

  DOI：10.1016/j.tetlet.2009.01.029

  日期：2009.4

  We synthesized C8-vinylpyrene-substituted 2'-deoxyguanosine (VPy)G and studied the photoregulated reversible E-Z isomerization. When E-isomer was irradiated with visible light (>420 nm), E- to Z-isomerization took place very rapidly, while upon irradiation with UV-Iight (similar to 365 nm), Z-isomer was converted to E-isomer. When Z-isomer was illuminated with 365-400 nm light, no fluorescence was observed, while F-isomer showed a very strong fluorescence emission, indicating that (VPy)G could be a useful fluorescence switching molecule. (C) 2009 Elsevier Ltd. All rights reserved.
• Design and synthesis of highly solvatochromic fluorescent 2′-deoxyguanosine and 2′-deoxyadenosine analogs
  作者：Katsuhiko Matsumoto、Naoya Takahashi、Azusa Suzuki、Takashi Morii、Yoshio Saito、Isao Saito

  DOI：10.1016/j.bmcl.2010.11.129

  日期：2011.2

  We synthesized various substituted 8-styryl-2'-deoxyguanosine and 8-styryl-2'-deoxyadenosine derivatives. Among them only acetyl substituted 8-styryl-2'-deoxyguanosine analog 5b showed a remarkable solvatochromicity (Delta lambda(em)(max) = 91 nm), that is, strong fluorescence at 477 nm in 1,4-dioxane, but in methanol the fluorescence was red shifted to 558 nm with very low intensity. Such environmentally sensitive solvatochromic fluorescent guanosine analogs may be useful as a sensor for investigating interactions of DNA with DNA binding proteins. (C) 2010 Elsevier Ltd. All rights reserved.
• DNA duplexes stabilized by modified monomer residues: synthesis and stability
  作者：Duncan Graham、John A. Parkinson、Tom Brown

  DOI：10.1039/a707031d

  日期：——

  The synthesis of a series of 2′-deoxyuridine analogues modified at the 5-position and a series of 2′-deoxypurines modified at the 8-position is described. Ultraviolet melting studies have been used to assess the stability of DNA duplexes 12- and 8-residues in length that contain these modifications. Of those modified residues which have been incorporated into oligonucleotides, 5-(prop-1-ynyl)-2′-deoxyuridine is found to impart the greatest increase in stability on the DNA duplexes studied.Thermodynamic analyses show that the reason for this increase in stability arises from a decrease in enthalpy which is related to the DNA base stacking process. We suggest that the degree of stabilisation imparted by the propyne moiety may be sequence dependent.

  本文描述了一系列在 5 位修饰的 2′-脱氧尿苷类似物和一系列在 8 位修饰的 2′-脱氧尿苷的合成过程。紫外线熔解研究被用来评估含有这些修饰的 12 位和 8 位 DNA 双链的稳定性。热力学分析表明，稳定性增加的原因是与 DNA 碱基堆叠过程有关的焓的降低。我们认为丙炔分子的稳定程度可能与序列有关。
• Synthesis of novel push–pull-type solvatochromic 2′-deoxyguanosine derivatives with longer wavelength emission
  作者：Yoshio Saito、Azusa Suzuki、Kazutoshi Imai、Nobukatsu Nemoto、Isao Saito

  DOI：10.1016/j.tetlet.2010.03.012

  日期：2010.5

  We synthesized novel push-pull-type fluorescent guanosine derivatives, (CN)G and (Ac)G containing 1,6- and 2,7-disubstituted pyrene chromophores. 1,6-Disubstituted pyrene derivatives, 1,6-(CN)G (3b) and 1,6-(Ac)G (3c), exhibited highly solvatochromic fluorescence emission at longer wavelength (similar to 540 nm). The environmentally sensitive fluorescent deoxyguanosines such as 3b and 3c can be used as powerful tools for structural studies of nucleic acids and molecular diagnostics. (C) 2010 Elsevier Ltd. All rights reserved.