(2R,5R)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-5-(pyren-1-yl)tetrahydrofuran-3-ol | 180611-79-4

• 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: (2R,5R)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-5-(pyren-1-yl)tetrahydrofuran-3-ol
• 英文别名: (2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-pyren-1-yloxolan-3-ol
• CAS: 180611-79-4
• 化学式: C₄₂H₃₆O₅
• 分子量: 620.745
• InChiKey: JZZWHVGAJJWKSN-LCKTVPPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  47.0
• 可旋转键数：
  9.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2R,5R)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-5-(pyren-1-yl)tetrahydrofuran-3-ol 在 吡啶 、 二氯乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 12.75h， 生成 3'-O-acetyl-1-pyrene β-deoxynucleoside
  参考文献：
  名称：

  Polymerase incorporation of pyrene-nucleoside triphosphates

  摘要：

  Pyrene-deoxynucleoside triphosphates (dPTPs), varying by the positioning of the aromatic system, were synthesized. Their ability to function as substrates for the Klenow fragment of Escherichia coli DNA polymerase I and the TdT polymerase was assessed. The dPTPs are all equally well tolerated by the Klenow fragment, and lead to elongation of up to 5 extra nucleotides of a ssDNA primer in a TdT-mediated reaction. The tailing efficiency of the dPTPs compares favorably to other less drastically modified dNTPs. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.101
• 作为产物：
  描述：

  2-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythro-pentofuranosyl chloride 在 吡啶 、 4-二甲氨基吡啶 、 sodium methylate 、 magnesium 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 (2R,5R)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-5-(pyren-1-yl)tetrahydrofuran-3-ol
  参考文献：
  名称：

  Local disruption of DNA-base stacking by bulky base surrogates

  摘要：

  一种新型的联苯基替代物在保持双链完整性的同时，破坏了2-氨基嘌呤碱基叠加。

  DOI：

  10.1039/b110842e

文献信息

• Templated chemistry for monitoring damage and repair directly in duplex DNA
  作者：Seoung Ho Lee、Shenliang Wang、Eric T. Kool

  DOI：10.1039/c2cc34060g

  日期：——

  We report the fluorogenic detection of the product of base excision repair (an abasic site) in a specific sequence of duplex DNA. This is achieved by DNA-templated chemistry, employing triple helix-forming probes that contain unnatural nucleobases designed to selectively recognize the site of a missing base. Light-up signals of up to 36-fold were documented, and probes could be used to monitor enzymatic removal of a damaged base.

  我们报告了在双链DNA特定序列中对碱基切除修复产物（一个去碱基位点）的荧光检测。这是通过DNA模板化化学实现的，采用了含有非天然核苷碱基的三重螺旋形成探针，旨在选择性识别缺失碱基的位置。记录到的荧光信号增强高达36倍，并且探针可以用于监测损伤碱基的酶促去除。
• Naphthalene, Phenanthrene, and Pyrene as DNA Base Analogues:  Synthesis, Structure, and Fluorescence in DNA
  作者：Rex X.-F. Ren、Narayan C. Chaudhuri、Pamela L. Paris、Rumney、Eric T. Kool

  DOI：10.1021/ja9612763

  日期：1996.1.1

  efficient method has also been developed for epimerization of the α-anomers to β-anomers by acid-catalyzed equilibration; this isomerization is successfully carried out on the four polycyclic nucleosides as well as two substituted phenyl nucleosides. The geometry of the anomeric substitution is derived from (1)H NOE experiments and is also correlated with a single-crystal X-ray structure of one α-isomer

  我们描述了携带多环芳烃的脱氧核糖核苷的合成、结构和 DNA 掺入作为 DNA“基础”类似物。新的多环化合物是 1-萘基、2-萘基、9-菲基和 1-芘基脱氧核苷。这些化合物是使用最近开发的 C-糖苷键形成方法合成的，该方法涉及芳香族化合物的有机镉衍生物与 1α-氯代脱氧核糖前体偶联。这种偶联的主要产物是脱氧核糖苷的 α-端基异构体。还开发了一种通过酸催化平衡将 α-端基异构体差向异构化为 β-端基异构体的有效方法；这种异构化成功地对四个多环核苷以及两个取代的苯基核苷进行。异头取代的几何形状源自 (1)H NOE 实验，并且还与一种 α-异构体的单晶 X 射线结构相关。三种多环 C-核苷衍生物通过其亚磷酰胺衍生物整合到 DNA 寡核苷酸中；芘基和菲基衍生物在 DNA 序列中显示出荧光。结果 (1) 拓宽了我们的 C-糖苷偶联反应的范围，(2) 证明（使用新的酸催化差向异构化）α-和 β-异头物
• An Excimer Clamp for Measuring Damaged‐Base Excision by the DNA Repair Enzyme NTH1
  作者：Yong Woong Jun、David L. Wilson、Anna M. Kietrys、Elizabeth R. Lotsof、Savannah G. Conlon、Sheila S. David、Eric T. Kool

  DOI：10.1002/anie.202001516

  日期：2020.5.4

  detection of damaged DNA base excision activity by a ratiometric fluorescence change. This strategy utilizes glycosylase-induced excimer formation of pyrenes, and modified DNA probes, incorporating two pyrene deoxynucleotides and a damaged base, enable the direct, real-time detection of NTH1 activity in vitro and in cellular lysates. The probe design was also applied in screening for potential NTH1 inhibitors

  直接测量 DNA 修复酶活性对于细胞修复途径的基础研究及其相关疾病的潜在新转化应用都很重要。NTH1 是一种针对氧化嘧啶的主要糖基化酶，可防止这种损伤引起的突变，并且 NTH1 活性的调节对于抵抗氧化应激和抑制肿瘤形成很重要。在此，我们描述了一种通过比率荧光变化直接检测受损 DNA 碱基切除活性的新型分子策略。该策略利用糖基化酶诱导芘的准分子形成和修饰的 DNA 探针，结合两个芘脱氧核苷酸和一个受损的碱基，能够在体外和细胞裂解物中直接、实时检测 NTH1 活性。
• Polycyclic Aromatic DNA-Base Surrogates: High-Affinity Binding to an Adenine-Specific Base-Flipping DNA Methyltransferase
  作者：Christine Beuck、Ishwar Singh、Anupam Bhattacharya、Walburga Hecker、Virinder S. Parmar、Oliver Seitz、Elmar Weinhold

  DOI：10.1002/anie.200219972

  日期：2003.8.25
• NOVEL NUCLEOSIDE ANALOGS WITH POLYCYCLIC AROMATIC GROUPS ATTACHED, METHODS OF SYNTHESIS AND USES THEREFOR
  申请人：University of Rochester

  公开号：EP0927188B1

  公开（公告）日：2004-09-08