3'-O,5'-O-bis(tert-butyldimethylsilyl)-O⁶-(2''-(4'''-nitrophenyl)ethyl)-2'-deoxyguanosine | 147299-48-7

• 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'-O,5'-O-bis(tert-butyldimethylsilyl)-O⁶-(2''-(4'''-nitrophenyl)ethyl)-2'-deoxyguanosine
• 英文别名: 3',5'O-bis(tert-butyldimethylsilyl)-O⁶-(p-nitrophenylethyl)-2'-deoxyguanosine；O⁶-(-p-Nitrophenylethyl)-3',5'-bis(tert-butyldimethylsilyl)-2'-desoxyguanosin；3',5'-O-Di-tert-butyldimethylsilyl-6-O-[2-(4-nitrophenyl)ethyl]-2'-deoxyguanosine；9-[(2R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]-6-[2-(4-nitrophenyl)ethoxy]purin-2-amine
• CAS: 147299-48-7
• 化学式: C₃₀H₄₈N₆O₆Si₂
• 分子量: 644.919
• InChiKey: ZYZPVQMYACLTHX-RBZQAINGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.64
• 重原子数：
  44
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  152
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3'-O,5'-O-bis(tert-butyldimethylsilyl)-O⁶-(2''-(4'''-nitrophenyl)ethyl)-2'-deoxyguanosine 在 吡啶 、 亚硝酸特丁酯 、 poly[4-vinylpyridinium poly(hydrogen fluoride)] 、 triethylamine tris(hydrogen fluoride) 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 37.0h， 生成 5'-O-(4,4'-Dimethoxytrityl)-6-O-[2-(4-nitrophenyl)ethyl]-2'-deoxy-2-fluoroinosine
  参考文献：
  名称：

  Synthesis and Hybridization Properties of Oligonucleotides Containing Polyamines at the C-2 Position of Purines: A Pre-synthetic Approach for the Incorporation of Spermine into Oligodeoxynucleotides Containing 2-(4,9,13-Triazatridecyl)-2′-deoxyguanosine

  摘要：

  We have developed a synthesis of spermine-containing oligonucleotides (ODN-sper) which allows incorporation of multiple polyamine residues. This approach was based on the pertrifluoroacetylated 5'DMT-dGsper phosphoramidite synthon. Its coupling yield with resin-bound ODN decreased dramatically when close to the 3'-end. Optimization of the coupling conditions allowed 22-mer ODNs containing up to six spermine residues to be synthesized. Several ODNs of different sequences with 1-4 pendent spermines could be purified and their hybridization properties were evaluated. Duplex melting temperatures increased linearly with the number of polyamine.residues (DeltaT(m)/sper = 3.0 +/- 0.2 degreesC in 100 mM NaCl). This compares very favorably with values reported for duplexes of similar initial stability containing other cation-substituted bases. Moreover, the stability increase was neither sequence nor position-dependent, and even contiguous spermine residues did not crosstalk. Extrapolation based on these findings leads to the conclusion that a duplex formed with a 22-mer oligonucleotide containing seven spermine residues would be as stable as genomic DNA, which highlights its potential for DNA strand invasion.

  DOI：

  10.1002/1521-3765(20001117)6:22<4188::aid-chem4188>3.0.co;2-n
• 作为产物：
  描述：

  2'-脱氧鸟苷 在 咪唑 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 50.0h， 生成 3'-O,5'-O-bis(tert-butyldimethylsilyl)-O⁶-(2''-(4'''-nitrophenyl)ethyl)-2'-deoxyguanosine
  参考文献：
  名称：

  吡咯衍生的双功能亲电试剂的 DNA 链间交联反应：DNA 中共同靶位点的证据

  摘要：

  由吡咯衍生的双功能亲电试剂家族鉴定的 DNA 链间交联位点在合成 DNA 双链体中进行了体外研究。该家族包括还原活化的丝裂霉素 C (1)、氧化活化的吡咯里西啶生物碱（例如 2）、简单的吡咯 2,3- 和 3,4-双-（乙酰氧基甲基）-1-甲基吡咯（3 和 4），以及抗肿瘤剂物质 2,3-二氢-5-(3',4'-二氯苯基)-6,7-双(羟甲基)-1H-吡咯嗪双-(异丙基氨基甲酸酯) (IPP, 5)。本文证明这些试剂优先交联双链 DNA 中的共同靶位点，即序列 5'-d(CG) 处脱氧鸟苷残基的环外氨基

  DOI：

  10.1021/ja00062a002

文献信息

• Stable and Selective Antiparallel Type Triplex DNA Formation by Targeting a GC Base Pair with the TFO Containing One &lt;i&gt;N&lt;/i&gt;&lt;sup&gt;2&lt;/sup&gt;-Phenyl-2′-deoxyguanosine
  作者：Yosuke Taniguchi、Mei Miyazaki、Nozomu Matsueda、Lei Wang、Hidenori Okamura、Shigeki Sasaki

  DOI：10.1248/cpb.c18-00043

  日期：2018.6.1

  osine (PhdG) showed a stable and selective triplex DNA formation with the GC base pair as compared to the natural dG/GC triplet. However, the multiple incorporation of PhdG into the TFOs hampered the stable triplex DNA, instead, showed a tendency to form a higher order structure. Therefore, we concluded that the stable and selective triplex DNA formation is expected by the replacement of dG by PhdG

  反平行三链体DNA是由富含嘌呤的三链体形成寡核苷酸（TFO）与双链体DNA中的同嘌呤区之间的相互作用形成的。这种具有基因组DNA的结构的形成有望控制活细胞中的基因表达。在这项研究中，为了增强三链DNA的稳定性，我们设计了N2-芳基化的脱氧鸟苷衍生物。在这些类似物中，我们发现与天然dG / GC三联体相比，含有N2-苯基-2'-脱氧鸟苷（PhdG）的TFO具有稳定的，选择性的三联DNA形成，并带有GC碱基对。但是，将PhdG多次掺入TFO阻碍了稳定的三链DNA，相反，它倾向于形成更高阶的结构。所以，
• N² -Substituted 2′-Deoxyguanosine Triphosphate Derivatives as Selective Substrates for Human DNA Polymerase κ
  作者：A. S. Prakasha Gowda、Marietta Lee、Thomas E. Spratt

  DOI：10.1002/anie.201611607

  日期：2017.3.1

  N2‐Alkyl‐2′‐deoxyguanosine triphosphate (N2‐alkyl‐dGTP) derivatives with methyl, butyl, benzyl, or 4‐ethynylbenzyl substituents were prepared and tested as substrates for human DNA polymerases. N2‐Benzyl‐dGTP was equal to dGTP as a substrate for DNA polymerase κ (pol κ), but was a poor substrate for pols β, δ, η, ι, or ν. In vivo reactivity was evaluated through incubation of N2‐4‐ethynylbenzyl‐dG

  Ñ 2 -烷基-2'-脱氧鸟苷三磷酸（N 2 -烷基的dGTP）制备具有甲基，丁基，苄基，或4-乙炔基苄基取代基的衍生物和作为用于人DNA聚合酶的底物进行测试。N 2-苄基-dGTP等于dGTP作为DNA聚合酶κ（polκ）的底物，但对于polsβ，δ，η，ι或ν则是较差的底物。体内的反应性是通过N个孵化评价2 -4-乙炔基苄基-dG的用野生型和polκ缺陷型小鼠胚胎成纤维细胞。CuAAC与5（6）-FAM-叠氮化物的反应表明，只有含有polκ的细胞才能掺入N 2-4-乙炔基苄基-dG进入细胞核。这是Y家族聚合酶特异性dNTP的第一个实例，该方法可用于探测体内polκ的活性。
• Steinbrecher, Thomas; Wameling, Christa; Oesch, Franz, Angewandte Chemie, 1993, vol. 105, # 3, p. 408 - 410
  作者：Steinbrecher, Thomas、Wameling, Christa、Oesch, Franz、Seidel, Albrecht

  DOI：——

  日期：——
• A High-Yield Synthesis of Deoxy-2-Fluoroinosine and its Incorporation into Oligonucleotides.
  作者：Abdennaji Adib、Pierre F. Potier、Svetlana Doronina、Ivan Huc、Jean-Paul Behr

  DOI：10.1016/s0040-4039(97)00540-6

  日期：1997.4

  An improved synthesis of the deoxy-2-fluoroinosine nucleoside is described, that makes use of mild fluorination (polyvinylpyridinium polyhydrogenfluoride) and O-silyl deprotection (triethylamine trihydrofluoride) reactions. The derived 5'-dimethoxytrityl-2-fluoroinosine-3'-phosphoramidite was incorporated into 10-, 15- and 20- mer oligonucleotides containing up to 7 non-natural bases. (C) 1997 Published by Elsevier Science Ltd.
• DNA interstrand cross-linking reactions of pyrrole-derived, bifunctional electrophiles: evidence for a common target site in DNA
  作者：Jinsuk Woo、Snorri T. Sigurdsson、Paul B. Hopkins

  DOI：10.1021/ja00062a002

  日期：1993.5

  The site of DNA interstrand cross-linking identified by a family of pyrrole-derived bifunctional electrophiles was studied in vitro in synthetic DNA duplexes. This family includes reductively activated mitomycin C (1), oxidatively activated pyrrolizidine alkaloids (e.g. 2), the simple pyrroles 2,3- and 3,4-bis-(acetoxymethyl)-1-methylpyrrole (3 and 4), and the antitumor substance 2,3-dihydro-5-(3'

  由吡咯衍生的双功能亲电试剂家族鉴定的 DNA 链间交联位点在合成 DNA 双链体中进行了体外研究。该家族包括还原活化的丝裂霉素 C (1)、氧化活化的吡咯里西啶生物碱（例如 2）、简单的吡咯 2,3- 和 3,4-双-（乙酰氧基甲基）-1-甲基吡咯（3 和 4），以及抗肿瘤剂物质 2,3-二氢-5-(3',4'-二氯苯基)-6,7-双(羟甲基)-1H-吡咯嗪双-(异丙基氨基甲酸酯) (IPP, 5)。本文证明这些试剂优先交联双链 DNA 中的共同靶位点，即序列 5'-d(CG) 处脱氧鸟苷残基的环外氨基