3’,5’-O-bis(tert-butydimethylsilyl)-N²-phenoxyacetyl-2’-deoxyguanosine | 866724-08-5

• 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: 3’,5’-O-bis(tert-butydimethylsilyl)-N²-phenoxyacetyl-2’-deoxyguanosine
• 英文别名: 3',5'-O-bis(tert-butyldimethylsilyl)-2-N-phenoxyacetyldeoxyguanosine；2-N-phenoxyacetyl-3',5'-di-O-t-butyldimethylsilyl-2'-deoxyguanosine；N-[9-[(2R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]-6-oxo-1H-purin-2-yl]-2-phenoxyacetamide
• CAS: 866724-08-5
• 化学式: C₃₀H₄₇N₅O₆Si₂
• 分子量: 629.904
• InChiKey: MTLVQLWDRCFVSD-WMTXJRDZSA-N

物化性质

• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.84
• 重原子数：
  43
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  125
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3’,5’-O-bis(tert-butydimethylsilyl)-N²-phenoxyacetyl-2’-deoxyguanosine 在 1-甲基吡咯烷 、 四丁基溴化铵 、 sodium carbonate 、 triethylamine tris(hydrogen fluoride) 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 33.5h， 生成 N-[6-(2-cyano-ethylsulfanyl)-9-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-2-yl]-2-phenoxy-acetamide
  参考文献：
  名称：

  Remarkable stabilization of antiparallel DNA triplexes by strong stacking effects of consecutively modified nucleobases containing thiocarbonyl groups

  摘要：

  The consecutive arrangement of 2'-deoxy-6-thioguanosines (s(6)Gs) and 4-thiothymidines (s(4)Ts) in antiparallel triplex-forming oligonucleotides (TFOs) considerably stabilized the resulting antiparallel triplexes with high base recognition ability by the strong stacking effects of thiocarbonyl groups. This result was remarkable because chemical modifications of the sugar moieties and nucleobases of antiparallel TFOs generally destabilize triplex structures. Moreover, in comparison with unmodified TFOs, it was found that TFOs containing s(6)Gs and s(4)Ts could selectively bind to the complementary DNA duplex but not to mismatched DNA duplexes or single-stranded RNA. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.079
• 作为产物：
  描述：

  N²-(phenoxyacetyl)-2'-deoxyguanosine 、 叔丁基二甲基氯硅烷 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 作用下， 以 氯仿 为溶剂， 反应 16.0h， 以86%的产率得到3’,5’-O-bis(tert-butydimethylsilyl)-N²-phenoxyacetyl-2’-deoxyguanosine
  参考文献：
  名称：

  O6-烷基鸟嘌呤DNA烷基转移酶对链内交联DNA的修复活性受核苷酸间连接的影响。

  摘要：

  通过固相合成制备了在两个连续的2'-脱氧鸟苷（dG）的O 6原子之间包含亚烷基链内交联（IaCL）的寡核苷酸。包含丁烯和庚烯IaCL的双链体的紫外热变性研究表明，与未修饰的双链体相比，稳定性降低了20°C。这些IaCL DNA双链体的圆二色性谱显示出与B型DNA一致的特征。人O 6-烷基鸟嘌呤DNA烷基转移酶（hAGT）能够修复含有IaCL的双链体，对庚烯类似物的修复效率略高。有趣的是，与O 6相比，hAGT对这些IaCL的修复效率较低亚烷基连接的IaCL在相连的2'-脱氧鸟苷残基之间缺乏5'-3'-磷酸二酯键。这些结果表明，在dG的O 6原子处，hAGT对IaCL的活性水平受交联残基之间的主链磷酸二酯键的影响。

  DOI：

  10.1002/asia.201501253

文献信息

• The synthesis of a menthol derivative of 2-aminopurine as a fluorescent DNA lesion
  作者：Wouter F.J. Hogendorf、Carlo P. Verhagen、Erik Malta、Nora Goosen、Herman S. Overkleeft、Dmitri V. Filippov、Gijsbert A. Van der Marel

  DOI：10.1016/j.tet.2009.10.023

  日期：2009.12

  An efficient synthetic route to the phosphoramidite of a menthol functionalized guanosine analog is presented. Two procedures were executed for the key introduction of the 6′-allyl menthyl moiety. Stille vinylation on 6-O-tosylguanosine followed by cross-metathesis using an excess of allyl menthyl ether proved to be less efficient than a Stille coupling on the same tosylate using an advanced menthyl-allyl

  提出了一种合成薄荷醇官能化鸟苷类似物的亚磷酰胺的有效途径。对关键引入6'-烯丙基薄荷基部分执行了两个程序。事实证明，在6- O-甲苯磺酰基鸟苷上进行Stille乙烯基化，然后使用过量的烯丙基薄荷基醚进行交叉复分解，其效率不如使用高级薄荷基-烯丙基锡烷衍生物在相同甲苯磺酸酯上进行Stille偶联的效率低。使用亚磷酰胺方法将修饰的核苷掺入DNA 50聚体的过程顺利进行。
• Synthesis of oligodeoxynucleotides incorporating 2-N-carbamoylguanine and evaluation of the hybridization properties
  作者：Takeshi Sasami、Yoko Odawara、Akihiro Ohkubo、Mitsuo Sekine、Kohji Seio

  DOI：10.1016/j.bmc.2008.11.042

  日期：2009.2

  Previously, we reported 2-N-carbamoylguanine (cmG) as a guanine analog. We further studied the synthetic protocol and hybridization properties of oligodeoxynucleotides (ODNs) incorporating cmG. These ODNs were synthesized using the phosphoramidite of cmG without protection of the 6-O position. However, the isolated products were contaminated with deacylated products having guanine in place of cmG.

  以前，我们报道了2- N-氨基甲酰基鸟嘌呤（cmG）作为鸟嘌呤类似物。我们进一步研究了整合cmG的寡脱氧核苷酸（ODNs）的合成方案和杂交特性。这些ODN是使用cmG的亚磷酰胺合成的，没有保护6- O位置。然而，分离的产物被具有鸟嘌呤代替cmG的脱酰产物污染。合成过程的详细分析表明，脱酰作用是由氨基甲酰基部分与封端剂反应引起的。保护6- O位置抑制了副反应。分析了掺入cmG的DNA双链体的热稳定性。T m的分析 值表明，取决于侧翼碱基，cmG的碱基区分能力与标准鸟嘌呤相当或更高。
• BODIPY-modified 2′-deoxyguanosine as a novel tool to detect DNA damages
  作者：Takeji Takamura-Enya、Ryoko Ishii

  DOI：10.1016/j.bmcl.2011.05.084

  日期：2011.7

  BODIPY-modified 2'-deoxyguanosine was synthesized for use as a detection reagent for genotoxic compounds. BODIPY-FL is a well known fluorescence reagent whose fluorescent light emission diminishes near a guanine base by a photo-induced electron transfer process. We attached BODIPY-FI to the 5' position of the deoxyribose moiety of 2'-deoxyguanosine. Although this compound has low fluorescence activity, when depurination by the action of alkylating reagents and dG oxidation by singlet oxygen occurred, the emission of strong fluorescence was observed. BODIPY-dG was found, therefore, to be a very useful tool for selectively detecting DNA damaging activity particularly in natural environmental extracts. (C) 2011 Elsevier Ltd. All rights reserved.
• Remarkable stabilization of antiparallel DNA triplexes by strong stacking effects of consecutively modified nucleobases containing thiocarbonyl groups
  作者：Kenji Yamada、Yusaku Hattori、Takeshi Inde、Takashi Kanamori、Akihiro Ohkubo、Kohji Seio、Mitsuo Sekine

  DOI：10.1016/j.bmcl.2012.11.079

  日期：2013.2

  The consecutive arrangement of 2'-deoxy-6-thioguanosines (s(6)Gs) and 4-thiothymidines (s(4)Ts) in antiparallel triplex-forming oligonucleotides (TFOs) considerably stabilized the resulting antiparallel triplexes with high base recognition ability by the strong stacking effects of thiocarbonyl groups. This result was remarkable because chemical modifications of the sugar moieties and nucleobases of antiparallel TFOs generally destabilize triplex structures. Moreover, in comparison with unmodified TFOs, it was found that TFOs containing s(6)Gs and s(4)Ts could selectively bind to the complementary DNA duplex but not to mismatched DNA duplexes or single-stranded RNA. (c) 2012 Elsevier Ltd. All rights reserved.
• <i>O</i> ⁶ -Alkylguanine DNA Alkyltransferase Repair Activity Towards Intrastrand Cross-Linked DNA is Influenced by the Internucleotide Linkage
  作者：Derek K. O'Flaherty、Christopher J. Wilds

  DOI：10.1002/asia.201501253

  日期：2016.2

  Oligonucleotides containing an alkylene intrastrand cross‐link (IaCL) between the O6‐atoms of two consecutive 2′‐deoxyguanosines (dG) were prepared by solid‐phase synthesis. UV thermal denaturation studies of duplexes containing butylene and heptylene IaCL revealed a 20 °C reduction in stability compared to the unmodified duplexes. Circular dichroism profiles of these IaCL DNA duplexes exhibited signatures

  通过固相合成制备了在两个连续的2'-脱氧鸟苷（dG）的O 6原子之间包含亚烷基链内交联（IaCL）的寡核苷酸。包含丁烯和庚烯IaCL的双链体的紫外热变性研究表明，与未修饰的双链体相比，稳定性降低了20°C。这些IaCL DNA双链体的圆二色性谱显示出与B型DNA一致的特征。人O 6-烷基鸟嘌呤DNA烷基转移酶（hAGT）能够修复含有IaCL的双链体，对庚烯类似物的修复效率略高。有趣的是，与O 6相比，hAGT对这些IaCL的修复效率较低亚烷基连接的IaCL在相连的2'-脱氧鸟苷残基之间缺乏5'-3'-磷酸二酯键。这些结果表明，在dG的O 6原子处，hAGT对IaCL的活性水平受交联残基之间的主链磷酸二酯键的影响。