2′-amino-2′-deoxy-2′-N-(pyren-1-ylmethyl)-5′-O-(4,4′-dimethoxytrityl)uridine | 801220-49-5

• 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: 2′-amino-2′-deoxy-2′-N-(pyren-1-ylmethyl)-5′-O-(4,4′-dimethoxytrityl)uridine
• 英文别名: 1-[(2R,3R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxy-3-(pyren-1-ylmethylamino)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 801220-49-5
• 化学式: C₄₇H₄₁N₃O₇
• 分子量: 759.858
• InChiKey: GZCDJVYRPYMYMF-FDWGYNFJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  57
• 可旋转键数：
  12
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  119
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2′-amino-2′-deoxy-2′-N-(pyren-1-ylmethyl)-5′-O-(4,4′-dimethoxytrityl)uridine 在 吡啶 、 三乙基硅烷 、 二氯乙酸 、 4-二甲氨基吡啶 、 甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 21.5h， 生成 2′-amino-2′-deoxy-2′-N-methyl-2′-N-(pyren-1-ylmethyl)-5′-O-(4,4′-dimethoxytrityl)uridine
  参考文献：
  名称：

  Conformationally controlled high-affinity targeting of RNA or DNA by novel 2′-amino-DNA/LNA mixmers and pyrenyl-functionalized 2′-amino-DNA

  摘要：

  含有 2â²-N-甲基-2â²-N-（吡喃-1-基甲基）-2â²-氨基-DNA 单体的 9-Mer DNA 序列对 DNA 互补体的亲和力显著增强，而相应的 2â²-amino-DNA 单体则对双链的稳定性产生不利影响。通过加入四个 LNA 核苷酸，诱导 B-DNA 到 A-DNA 的构象变化，可以有效地逆转这些影响。

  DOI：

  10.1039/b411626g
• 作为产物：
  描述：

  2-pyrenecarboxaldehyde 、 5'-O-dimethoxytrityl-2'-amino-2'-deoxyuridine 在 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以70%的产率得到2′-amino-2′-deoxy-2′-N-(pyren-1-ylmethyl)-5′-O-(4,4′-dimethoxytrityl)uridine
  参考文献：
  名称：

  Conformationally controlled high-affinity targeting of RNA or DNA by novel 2′-amino-DNA/LNA mixmers and pyrenyl-functionalized 2′-amino-DNA

  摘要：

  含有 2â²-N-甲基-2â²-N-（吡喃-1-基甲基）-2â²-氨基-DNA 单体的 9-Mer DNA 序列对 DNA 互补体的亲和力显著增强，而相应的 2â²-amino-DNA 单体则对双链的稳定性产生不利影响。通过加入四个 LNA 核苷酸，诱导 B-DNA 到 A-DNA 的构象变化，可以有效地逆转这些影响。

  DOI：

  10.1039/b411626g

文献信息

• Recognition of Double-Stranded DNA Using Energetically Activated Duplexes Modified with N2′-Pyrene-, Perylene-, or Coronene-Functionalized 2′-<i>N</i>-Methyl-2′-amino-DNA Monomers
  作者：Brooke A. Anderson、Jared J. Onley、Patrick J. Hrdlicka

  DOI：10.1021/acs.joc.5b00742

  日期：2015.6.5

  Invader probes have been proposed as alternatives to polyamides, triplex-forming oligonucleotides, and peptide nucleic acids for recognition of chromosomal DNA targets. These double-stranded probes are activated for DNA recognition by +1 interstrand zippers of pyrene-functionalized nucleotides. This particular motif forces the intercalating pyrene moieties into the same region, resulting in perturbation and destabilization of the probe duplex. In contrast, the two probe strands display very high affinity toward complementary DNA. The energy difference between the probe duplexes and recognition complexes provides the driving force for DNA recognition. In the present study, we explore the properties of Invader probes based on larger intercalators, i.e., perylene and coronene, expecting that the larger pi-surface area will result in additional destabilization of the probe duplex and further stabilization of probe target duplexes, in effect increasing the thermodynamic driving force for DNA recognition. Toward this end, we developed protocols for 2'-N-methyl-2'-amino-2'-deoxyuridine phosphoramidites that are functionalized at the N2'-position with pyrene, perylene, or coronene moieties and incorporated these monomers into oligodeoxyribonudeotides (ONs). The resulting ONs and Invader probes are characterized by thermal denaturation experiments, analysis of thermodynamic parameters, absorption and fluorescence spectroscopy, and DNA recognition experiments. Invader probes based on large intercalators efficiently recognize model targets.
• Conformationally controlled high-affinity targeting of RNA or DNA by novel 2′-amino-DNA/LNA mixmers and pyrenyl-functionalized 2′-amino-DNA
  作者：Neerja Kalra、B. Ravindra Babu、Virinder S. Parmar、Jesper Wengel

  DOI：10.1039/b411626g

  日期：——

  9-Mer DNA sequences containing 2′-N-methyl-2′-N-(pyren-1-ylmethyl)-2′-amino-DNA monomers display significantly increased affinity towards DNA complements whereas the corresponding 2′-amino-DNA monomer has a detrimental effect on duplex stability. These effects are efficiently reversed by incorporation of four LNA nucleotides inducing a B-DNA to A-DNA conformational change.

  含有 2â²-N-甲基-2â²-N-（吡喃-1-基甲基）-2â²-氨基-DNA 单体的 9-Mer DNA 序列对 DNA 互补体的亲和力显著增强，而相应的 2â²-amino-DNA 单体则对双链的稳定性产生不利影响。通过加入四个 LNA 核苷酸，诱导 B-DNA 到 A-DNA 的构象变化，可以有效地逆转这些影响。