5'-O-[二(4-甲氧基苯基)苯基甲基]-2-硫代尿苷 | 163496-06-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 中文名称: 5'-O-[二(4-甲氧基苯基)苯基甲基]-2-硫代尿苷
• 英文名称: 5’-O-dimetoxytrityl-2-thiouridine
• 英文别名: 1-((2R,3R,4S,5R)-5-((Bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-3,4-dihydroxytetrahydrofuran-2-yl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one；1-[(2R,3R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-3,4-dihydroxyoxolan-2-yl]-2-sulfanylidenepyrimidin-4-one
• CAS: 163496-06-8
• 化学式: C₃₀H₃₀N₂O₇S
• 分子量: 562.643
• InChiKey: VEYJOLJIOJKZRE-YULOIDQLSA-N

物化性质

• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  142
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5'-O-[二(4-甲氧基苯基)苯基甲基]-2-硫代尿苷 在 sodium tetrahydroborate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 4.5h， 生成 5'-O-dimetoxytrityl-2-selenouridine
  参考文献：
  名称：

  Transformation of a wobble 2-thiouridine to 2-selenouridine via S-geranyl-2-thiouridine as a possible cellular pathway

  摘要：

  The newly discovered S-geranylated 2-thiouridines (geS2U) (Dumelin et al., 2012) and 2-selenouridines (Se2U) were recently shown to be synthesized by a single enzyme (selenouridine synthase, SelU) through two distinct pathways using the same 2-thiouridine substrate (S2U); however, no clear catalytic mechanism was proposed. We suggest that S-geranyl-2-thiouridine is an intermediate of the SelU-catalyzed conversion of S2U to Se2U. The successful chemical transformation of S2U -> geS2U -> Se2U is demonstrated here as an initial approximation of the intracellular pathway. The structure of Se2U was confirmed by spectroscopic methods, which included, for the first time, Se-77 NMR data (delta 354 ppm). (C) 2014 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2014.05.012
• 作为产物：
  描述：

  4,4'-双甲氧基三苯甲基氯 、 2-硫代尿苷 在 吡啶 作用下， 生成 5'-O-[二(4-甲氧基苯基)苯基甲基]-2-硫代尿苷
  参考文献：
  名称：

  细菌tRNA的S -Geylyl-2-thiouridine摆动核苷; S -geranylated-RNAs的化学和酶促合成及其理化特性

  摘要：

  最近，在Lys，Glu和Gln特异的细菌tRNA的第一个（摆动）反密码子位置发现了5-甲基氨基甲基-2-硫尿苷（mnm5geS2U）和5-羧甲基氨基甲基-2-硫尿苷（cmnm5geS2U）的高度亲脂性S -geranylated衍生物。 。这些独特的tRNA的功能和细胞生物发生仍然知之甚少。在这里，我们介绍一种直接和两种合成后的化学路线，用于制备模型geS2U-RNA。我们的实验数据表明，geS2U-RNA比其亲本S2U-RNA和未修饰的U-RNA更具亲脂性。热力学研究表明，S含-geranyl-2-thiouridine的RNA对与互补单元相反的G的互补RNA链具有更高的亲和力。重组tRNA硒基尿苷合酶（SelU）对S2U-RNA模型具有硫特异性的Geranylation活性，该S2U-RNA由S2U-RNA组成人类tRNA Lys3序列的反密码子-茎-环（ASL）。另外，需要镁离子的存在才能达到明显的香叶酰化效率。

  DOI：

  10.1093/nar/gkw727

文献信息

• Novel RNA base pair with higher specificity using single selenium atom
  作者：Huiyan Sun、Jia Sheng、Abdalla E. A. Hassan、Sibo Jiang、Jianhua Gan、Zhen Huang

  DOI：10.1093/nar/gks010

  日期：2012.6.1

  Specificity of nucleobase pairing provides essential foundation for genetic information storage, replication, transcription and translation in all living organisms. However, the wobble base pairs, where U in RNA (or T in DNA) pairs with G instead of A, might compromise the high specificity of the base pairing. The U/G wobble pairing is ubiquitous in RNA, especially in non-coding RNA. In order to increase U/A pairing specificity, we have hypothesized to discriminate against U/G wobble pair by tailoring the steric and electronic effects at the 2-exo position of uridine and replacing the 2-exo oxygen with a selenium atom. We report here the first synthesis of the 2-Se-U-RNAs as well as the 2-Se-uridine ( Se U) phosphoramidite. Our biophysical and structural studies of the Se U-RNAs indicate that this single atom replacement can indeed create a novel U/A base pair with higher specificity than the natural one. We reveal that the Se U/A pair maintains a structure virtually identical to the native U/A base pair, while discriminating against U/G wobble pair. This oxygen replacement with selenium offers a unique chemical strategy to enhance the base pairing specificity at the atomic level.

  核碱基配对的特异性为所有生物的遗传信息存储、复制、转录和翻译提供了重要基础。然而，摇摆碱基配对，即 RNA 中的 U（或 DNA 中的 T）与 G 而不是 A 配对，可能会损害碱基配对的高度特异性。在 RNA 中，尤其是在非编码 RNA 中，U/G 摆动配对无处不在。为了提高 U/A 配对的特异性，我们假设通过调整尿苷的 2-exo 位的立体和电子效应，并用一个硒原子取代 2-exo 氧原子，来区分 U/G 摇摆配对。我们在此报告了 2-Se-U-RNA 以及 2-Se-uridine ( Se U) 磷酰胺的首次合成。我们对 Se U-RNA 的生物物理和结构研究表明，这种单原子置换确实可以产生比天然碱基对具有更高特异性的新型 U/A 碱基对。我们发现，Se U/A碱基对保持了与天然U/A碱基对几乎相同的结构，同时对U/G摆动碱基对具有识别作用。这种用硒替代氧的方法提供了一种独特的化学策略，在原子水平上提高了碱基配对的特异性。
• Transformation of a wobble 2-thiouridine to 2-selenouridine via S-geranyl-2-thiouridine as a possible cellular pathway
  作者：Paulina Bartos、Anna Maciaszek、Anna Rosinska、Elzbieta Sochacka、Barbara Nawrot

  DOI：10.1016/j.bioorg.2014.05.012

  日期：2014.10

  The newly discovered S-geranylated 2-thiouridines (geS2U) (Dumelin et al., 2012) and 2-selenouridines (Se2U) were recently shown to be synthesized by a single enzyme (selenouridine synthase, SelU) through two distinct pathways using the same 2-thiouridine substrate (S2U); however, no clear catalytic mechanism was proposed. We suggest that S-geranyl-2-thiouridine is an intermediate of the SelU-catalyzed conversion of S2U to Se2U. The successful chemical transformation of S2U -> geS2U -> Se2U is demonstrated here as an initial approximation of the intracellular pathway. The structure of Se2U was confirmed by spectroscopic methods, which included, for the first time, Se-77 NMR data (delta 354 ppm). (C) 2014 Elsevier Inc. All rights reserved.
• <i>S</i>-Geranyl-2-thiouridine wobble nucleosides of bacterial tRNAs; chemical and enzymatic synthesis of<i>S</i>-geranylated-RNAs and their physicochemical characterization
  作者：Malgorzata Sierant、Grazyna Leszczynska、Klaudia Sadowska、Agnieszka Dziergowska、Michal Rozanski、Elzbieta Sochacka、Barbara Nawrot

  DOI：10.1093/nar/gkw727

  日期：2016.12.15

  understood. Here, we present one direct and two post-synthetic chemical routes for preparing model geS2U-RNAs. Our experimental data demonstrate that geS2U-RNAs are more lipophilic than their parent S2U-RNAs as well as non-modified U-RNAs. Thermodynamic studies revealed that the S-geranyl-2-thiouridine-containing RNA has higher affinity toward complementary RNA strand with G opposite the modified unit

  最近，在Lys，Glu和Gln特异的细菌tRNA的第一个（摆动）反密码子位置发现了5-甲基氨基甲基-2-硫尿苷（mnm5geS2U）和5-羧甲基氨基甲基-2-硫尿苷（cmnm5geS2U）的高度亲脂性S -geranylated衍生物。 。这些独特的tRNA的功能和细胞生物发生仍然知之甚少。在这里，我们介绍一种直接和两种合成后的化学路线，用于制备模型geS2U-RNA。我们的实验数据表明，geS2U-RNA比其亲本S2U-RNA和未修饰的U-RNA更具亲脂性。热力学研究表明，S含-geranyl-2-thiouridine的RNA对与互补单元相反的G的互补RNA链具有更高的亲和力。重组tRNA硒基尿苷合酶（SelU）对S2U-RNA模型具有硫特异性的Geranylation活性，该S2U-RNA由S2U-RNA组成人类tRNA Lys3序列的反密码子-茎-环（ASL）。另外，需要镁离子的存在才能达到明显的香叶酰化效率。