5'-O-dimethoxytrityl-3'-O-tert-butyldimethylsilyl-4-(N-1-triazoyl)-2'-deoxyuridine | 338799-25-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 5'-O-dimethoxytrityl-3'-O-tert-butyldimethylsilyl-4-(N-1-triazoyl)-2'-deoxyuridine
• 英文别名: 3’-O-(tert-butyldimethylsilyl)-5’-O-(4,4’-dimethoxytrityl)-C4-(1,2,4-triazol-1-yl)-2’-deoxyuridine；3’-O-(t-butyldimethylsilyl)-5’-O-(4,4’-dimethoxytrityl)-4-triazolyl-2’-deoxyuridine；5’-O-dimethoxytrityl-3’-O-tert-butyldimethylsilyl-N⁴-triazole-2’-deoxyuridine；1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[tert-butyl(dimethyl)silyl]oxyoxolan-2-yl]-4-(1,2,4-triazol-1-yl)pyrimidin-2-one
• CAS: 338799-25-0
• 化学式: C₃₈H₄₅N₅O₆Si
• 分子量: 695.891
• InChiKey: VYPYDESFKUROEJ-VUHKNJSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.53
• 重原子数：
  50.0
• 可旋转键数：
  12.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  111.75
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  5'-O-dimethoxytrityl-3'-O-tert-butyldimethylsilyl-4-(N-1-triazoyl)-2'-deoxyuridine 在 四丁基氟化铵 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 17.0h， 生成
  参考文献：
  名称：

  O⁶-Alkylguanine-DNA Alkyltransferase-Mediated Repair ofO⁴-Alkylated 2′-Deoxyuridines

  摘要：

  AbstractO6‐Alkylguanine‐DNA alkyltransferases (AGTs) are responsible for the removal of O6‐alkyl 2′‐deoxyguanosine (dG) and O4‐alkyl thymidine (dT) adducts from the genome. Unlike the E. coli OGT (O6‐alkylguanine‐DNA‐alkyltransferase) protein, which can repair a range of O4‐alkyl dT lesions, human AGT (hAGT) only removes methyl groups poorly. To uncover the influence of the C5 methyl group of dT on AGT repair, oligonucleotides containing O4‐alkyl 2′‐deoxyuridines (dU) were prepared. The ability of E. coli AGTs (Ada‐C and OGT), human AGT, and an OGT/hAGT chimera to remove O4‐methyl and larger adducts (4‐hydroxybutyl and 7‐hydroxyheptyl) from dU were examined and compared to those relating to the corresponding dT species. The absence of the C5 methyl group resulted in an increase in repair observed for the O4‐methyl adducts by hAGT and the chimera. The chimera was proficient at repairing larger adducts at the O4 atom of dU. There was no observed correlation between the binding affinities of the AGT homologues to adduct‐containing oligonucleotides and the amounts of repair measured.

  DOI：

  10.1002/cbic.201402169
• 作为产物：
  描述：

  2-脱氧尿苷 在 吡啶 、 咪唑 、 三乙胺 、 三氯氧磷 作用下， 以 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 9.0h， 生成 5'-O-dimethoxytrityl-3'-O-tert-butyldimethylsilyl-4-(N-1-triazoyl)-2'-deoxyuridine
  参考文献：
  名称：

  含有具有磷酸二酯功能的胞嘧啶类似物的新型核苷酸单元的合成和银（I）介导的 DNA 双链体的形成

  摘要：

  摘要 合成了具有磷酸二酯/硫代磷酸二酯功能的新型修饰的胞嘧啶类似物。通过紫外熔解实验研究了DNA双链体中不同金属离子和修饰的胞嘧啶-胞嘧啶碱基对之间的相互作用。与磷酸二酯对应物相比，硫代磷酸二酯修饰与 Ag(I) 离子的结合力更强，这在 ESI-MS 光谱中也进行了检查。

  DOI：

  10.1080/15257770.2022.2100903

文献信息

• Synthesis and Characterization of DNA Duplexes Containing an N⁴C−Ethyl−N⁴C Interstrand Cross-Link
  作者：David M. Noll、Anne M. Noronha、Paul S. Miller

  DOI：10.1021/ja003340t

  日期：2001.4.1

  Short DNA duplexes containing an N(4)C-ethyl-N(4)C interstrand cross-link, C-C, were synthesized on controlled pore glass supports. Duplexes having two, three, or four A/T base pairs on either side of the C-C cross-link and terminating with a C(4) overhang at their 5'-ends were prepared. The cross-link was introduced using a convertible nucleoside approach. Thus, an oligonucleotide terminating at its

  包含 N(4)C-乙基-N(4)C 链间交联、CC 的短 DNA 双链体在受控孔玻璃支持物上合成。准备了在 CC 交联两侧具有两个、三个或四个 A/T 碱基对并在其 5' 末端以 C(4) 悬垂终止的双工。使用可转换核苷方法引入交联。因此，首先在载体上制备了在其 5'-末端带有 O(4)-triazoyl-2'-deoxyuridine 的寡核苷酸。与载体结合的低聚物的三唑基团被 5'-二甲氧基三苯甲基-3'-O-叔丁基二甲基甲硅烷基-N(4)-(2-氨基乙基)脱氧胞苷的氨基乙基基团取代以产生交联。二甲氧基三苯甲基被去除，双链体的上下链从两个5'端延伸 -使用受保护的核苷 3'-亚磷酰胺交联的羟基。然后除去所得部分双链体的叔丁基二甲基甲硅烷基，并使用受保护的核苷5'-亚磷酰胺从所得交联的3'-羟基沿3'-方向延伸链。交联的双链体通过 HPLC 纯化，并通过酶消化和 MALDI-TOF 质谱法表征。在
• Synthesis and anti-HIV-1 integrase activity of modified dinucleotides
  作者：Yves Aubert、Marcel Chassignol、Victoria Roig、Gladys Mbemba、Julien Weiss、Hervé Meudal、Jean-François Mouscadet、Ulysse Asseline

  DOI：10.1016/j.ejmech.2009.09.007

  日期：2009.12

  The synthesis of a series of thirty-eight new modified dinucleotides and dinucleotide conjugate analogues of d-5′ApC3′ is described. The inhibitory activity of these compounds toward HIV-1 integrase was examined in enzymatic assays using the natural dinucleotide as a reference. Among the compounds, a perylene-dinucleotide conjugate has shown a two micromolar anti-integrase activity due to the presence

  一系列38新型改性二核苷酸和D-的二核苷酸偶联物类似物的合成5' APC 3'进行说明。这些酶对HIV-1整合酶的抑制活性在酶法测定中以天然二核苷酸为参考进行了检测。在这些化合物中，由于嵌入剂和二核苷酸的存在，a-二核苷酸缀合物具有两个微摩尔的抗整合酶活性。
• SYNTHESES OF DNA DUPLEXES CONTAINING A C‒C INTERSTRAND CROSS-LINK
  作者：Anne M. Noronha、David M. Noll、Paul S. Miller

  DOI：10.1081/ncn-100002542

  日期：2001.3.31

  Short DNA duplexes that contain a N4C-ethyl-N4C interstrand cross-link were prepared on controlled pore glass supports using a DNA synthesizer. The C-C cross-link was introduced via a convertible nucleoside on the support or by using a protected C-C cross-link phosphoramidite. An orthogonal protection scheme allowed selective chain growth in either a 3'-->5' or 5'-->3' direction. The cross-linked duplexes

  使用DNA合成仪在可控孔玻璃载体上制备了包含N4C-乙基-N4C链间交联的短DNA双链体。通过载体上的可转换核苷或使用受保护的CC交联亚磷酰胺引入CC交联。正交保护方案允许选择性链在3'-> 5'或5'-> 3'方向上生长。通过HPLC纯化交联的双链体，并通过MALDI-TOF质谱和/或通过酶消化进行表征。
• Structural basis of interstrand cross-link repair by O⁶-alkylguanine DNA alkyltransferase
  作者：Alexey Y. Denisov、Francis P. McManus、Derek K. O'Flaherty、Anne M. Noronha、Christopher J. Wilds

  DOI：10.1039/c7ob02093g

  日期：——

  E.coli (OGT and Ada-C) AGTs with comparably low μM dissociation constants for 2:1 or 4:1 AGT/DNA stoichiometries. The solution structures of two heptylene linked DNA duplexes (CGAAAYTTTCG)2, XLUU7 (Y=dU) and XLGG7 (Y=dG), were solved and the global structures were virtually identical with a RMSD of 1.22 Å. The ICL was found to reside in the major groove for both duplexes. The linkage adopts an E conformation

  DNA链间交联（ICL）是生物系统中发现的最具细胞毒性的病变之一。O 6-烷基鸟嘌呤DNA烷基转移酶（AGT）能够去除2'-脱氧鸟苷的O 6-原子和胸苷的O 4-原子的烷基化损伤。人类AGT（hAGT）已显示出修复链间交联（ICL）双链体的能力，其中2'-脱氧鸟苷的两个O 6原子通过丁烯（XLGG4）或庚烯（XLGG7）链连接。然而，发现胸苷的O 4原子之间的类似ICL逃避了修复。连接O的ICL双工已经准备了通过丁烯（ XLUU4）或庚烯（ XLUU7）键的2'-脱氧尿苷的4个原子，以研究C5甲基对AGT介导的修复的影响。既XLUU4和XLUU7难治由人力和修理大肠杆菌（OGT和Ada-C）与AGTS相对低μM解离常数为2：1或4：1个AGT / DNA的化学计量。两个庚烯连接的DNA双链体（CGAAAYTTTCG） 2， XLUU7（Y = dU）和XLGG7的溶液结构（Y = dG）被求解，总体结构几乎相同，RMSD为1