O⁶-((2,4,6-Triisopropylphenyl)sulfonyl)-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyinosine | 149035-74-5

• 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: O⁶-((2,4,6-Triisopropylphenyl)sulfonyl)-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyinosine
• 英文别名: 3'-5'-O-di(tert-butyldimethylsilyl)-6-O-(2,4,6-triisopropylbenzenesulfonyl)-2'-deoxyinosine；[9-[(2R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]purin-6-yl] 2,4,6-tri(propan-2-yl)benzenesulfonate
• CAS: 149035-74-5
• 化学式: C₃₇H₆₂N₄O₆SSi₂
• 分子量: 747.159
• InChiKey: YHVZDYLHNBQOHH-OJDZSJEKSA-N

物化性质

• 沸点：
  709.1±70.0 °C(predicted)
• 密度：
  1.13±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.66
• 重原子数：
  50
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  123
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  O⁶-((2,4,6-Triisopropylphenyl)sulfonyl)-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyinosine 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 169.0h， 生成 2-N-(1-(3-nitrodibenzofuran-2-yl))ethyl-2'-deoxyadenosine
  参考文献：
  名称：

  dA和dC残留物的波长选择性解笼

  摘要：

  硝基二苯并呋喃（NDBF）基团被用作对光不稳定的“笼型”基团，以暂时掩盖dA和dC残基的沃森-克里克相互作用。它们显示出改进的掩蔽能力，并且在这些位置的光脱保护效率比1-（邻硝基苯基）-乙基（NPE）笼蔽基团高12倍。此外，在NPE基团的存在下，NDBF基团可以波长选择性地除去。这将使寡核苷酸具有更复杂的（解笼）策略-超出通常的不可逆触发。

  DOI：

  10.1021/ol200141v
• 作为产物：
  描述：

  2'-脱氧肌苷 在 咪唑 、 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.58h， 生成 O⁶-((2,4,6-Triisopropylphenyl)sulfonyl)-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyinosine
  参考文献：
  名称：

  Synthesis of the Fjord-region cis- and trans-Amino Triol Derivatives of the Carcinogenic Hydrocarbon Benzo[g]chrysene and Utilization for the Synthesis of a Deoxyadenosine Adduct Linked to the N6-Amino Group

  摘要：

  Efficient syntheses of the complete set of four diastereomeric fjord-region amino triol derivatives of benzo[g]chrysene in which the amino group in the 14-position and the adjacent 13-hydroxyl group are trans or cis to one another (trans- and cis-5 and 6) is described. This is the first description of the syntheses of the bay- or fjord-region cis-amino triol derivatives of any carcinogenic polycyclic aromatic hydrocarbon(PAH). The amino triols are key synthetic precursors of PAH-oligonucleotide adducts in which the PAH moiety is covalently linked to the exocyclic amino groups of deoxyadenosine or deoxyguanosine. Formation of adducts of this type via reaction of a PAH diol epoxide metabolite with DNA is believed to be a critical step in the mechanism of PAH carcinogenesis. The synthetic amino triol isomers may be used to synthesize PAH-oligonucleotides needed for site-directed mutagenesis studies to relate isomer structural differences to their effects on DNA replication.

  DOI：

  10.1021/jo00124a027

文献信息

• A red-shifted two-photon-only caging group for three-dimensional photorelease
  作者：Yvonne Becker、Erik Unger、Manuela A. H. Fichte、Daniel A. Gacek、Andreas Dreuw、Josef Wachtveitl、Peter J. Walla、Alexander Heckel

  DOI：10.1039/c7sc05182d

  日期：——

  with higher two-photon action cross section and red-shifted absorption was developed. Due to calculations, a dimethylamino functionality (DMA) was added at ring position 7. The uncaging of nucleobases after two-photon excitation (2PE) could be visualized via double-strand displacement in a hydrogel. With this assay we achieved three-dimensional photorelease of DMA-NDBF-protected DNA orthogonal to NDBF-protected

  基于硝基二苯并呋喃（NDBF），开发了一种具有更高的双光子作用截面和红移吸收的新型光笼。由于计算，在环的第7位添加了二甲基氨基官能团（DMA）。通过在水凝胶中的双链置换，可以看到双光子激发（2PE）后核碱基的解开。通过该测定，我们实现了与NDBF保护的链正交的DMA-NDBF保护的DNA的三维照片释放。DMA-NDBF虽然是出色的2P笼，但在可见光单光子激发（1PE）下却出奇地稳定。激发特异性光化学的这种情况扩大了正交光调节的范围。
• Synthesis of oligodeoxynucleotides containing diastereomeric dihydrodiol epoxide-N6-deoxyadenosine adducts of polycyclic aromatic hydrocarbons
  作者：Thomas Steinbrecher、Andreas Becker、John J. Stezowski、Franz Oesch、Albrecht Seidel

  DOI：10.1016/s0040-4039(00)60775-x

  日期：1993.3

  A generally applicable route is reported for the synthesis of oligodeoxynucleotides which contain structurally defined N6-deoxyadenosine adducts, derived from sterically highly hindered dihydrodiol epoxides of polycyclic aromatic hydrocarbons (PAH).

  报道了合成寡核苷酸的通用途径，该寡核苷酸含有结构上定义的N 6-脱氧腺苷加合物，其衍生自多环芳族烃（PAH）的空间高度受阻的二氢二醇环氧化物。
• Wavelength-Selective Uncaging of dA and dC Residues
  作者：Florian Schäfer、Khashti Ballabh Joshi、Manuela A. H. Fichte、Timo Mack、Josef Wachtveitl、Alexander Heckel

  DOI：10.1021/ol200141v

  日期：2011.3.18

  Nitrodibenzofuran (NDBF) groups are used as photolabile “caging” groups to temporarily mask the Watson−Crick interaction of dA and dC residues. They show improved masking capabilities and are photodeprotected 12 times more efficiently than 1-(o-nitrophenyl)-ethyl (NPE) caging groups in these positions. Furthermore, NDBF groups can be removed wavelength-selectively in the presence of NPE groups. This

  硝基二苯并呋喃（NDBF）基团被用作对光不稳定的“笼型”基团，以暂时掩盖dA和dC残基的沃森-克里克相互作用。它们显示出改进的掩蔽能力，并且在这些位置的光脱保护效率比1-（邻硝基苯基）-乙基（NPE）笼蔽基团高12倍。此外，在NPE基团的存在下，NDBF基团可以波长选择性地除去。这将使寡核苷酸具有更复杂的（解笼）策略-超出通常的不可逆触发。
• Synthesis of the Fjord-region cis- and trans-Amino Triol Derivatives of the Carcinogenic Hydrocarbon Benzo[g]chrysene and Utilization for the Synthesis of a Deoxyadenosine Adduct Linked to the N6-Amino Group
  作者：Alexander S. Kiselyov、Thomas Steinbrecher、Ronald G. Harvey

  DOI：10.1021/jo00124a027

  日期：1995.9

  Efficient syntheses of the complete set of four diastereomeric fjord-region amino triol derivatives of benzo[g]chrysene in which the amino group in the 14-position and the adjacent 13-hydroxyl group are trans or cis to one another (trans- and cis-5 and 6) is described. This is the first description of the syntheses of the bay- or fjord-region cis-amino triol derivatives of any carcinogenic polycyclic aromatic hydrocarbon(PAH). The amino triols are key synthetic precursors of PAH-oligonucleotide adducts in which the PAH moiety is covalently linked to the exocyclic amino groups of deoxyadenosine or deoxyguanosine. Formation of adducts of this type via reaction of a PAH diol epoxide metabolite with DNA is believed to be a critical step in the mechanism of PAH carcinogenesis. The synthetic amino triol isomers may be used to synthesize PAH-oligonucleotides needed for site-directed mutagenesis studies to relate isomer structural differences to their effects on DNA replication.