5'-O-(4,4'-dimethoxytrityl)-2'-C-[4-(pyrene-1-ylcarbonyl)-1H-1,2,3-triazol-1-yl]-2'-deoxyuridine | 1350452-69-5

• 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: 5'-O-(4,4'-dimethoxytrityl)-2'-C-[4-(pyrene-1-ylcarbonyl)-1H-1,2,3-triazol-1-yl]-2'-deoxyuridine
• 英文别名: 1-[(2R,3R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxy-3-[4-(pyrene-1-carbonyl)triazol-1-yl]oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 1350452-69-5
• 化学式: C₄₉H₃₉N₅O₈
• 分子量: 825.877
• InChiKey: XDEZDVCUTOIAOS-JEERDGSXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  62
• 可旋转键数：
  12
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  154
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  5'-O-(4,4'-dimethoxytrityl)-2'-C-[4-(pyrene-1-ylcarbonyl)-1H-1,2,3-triazol-1-yl]-2'-deoxyuridine 、 双(二异丙基氨基)(2-氰基乙氧基)膦 在 四氮唑 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 3.5h， 以59%的产率得到3'-O-(N,N-diisopropylamino-2-cyanoethoxyphosphinyl)-5'-O-(4,4'-dimethoxytrityl)-2'-C-[4-(pyrene-1-ylcarbonyl)-1H-1,2,3-triazol-1-yl]-2'-deoxyuridine
  参考文献：
  名称：

  C2′-Pyrene-Functionalized Triazole-Linked DNA: Universal DNA/RNA Hybridization Probes

  摘要：

  Development of universal hybridization probes, that is, oligonudeotides displaying identical affinity toward matched and mismatched DNA/RNA targets, has been a longstanding goal due to potential applications as degenerate PCR primers and microarray probes. The classic approach toward this end has been the use of "universal bases" that either are based on hydrogen-bonding purine derivatives or aromatic base analogues without hydrogen-bonding capabilities. However, development of probes that result in truly universal hybridization without compromising duplex thermostability has proven challenging. Here we have used the "click reaction" to synthesize four C2'-pyrenefunctionalized triazole-linked 2'-deoxyuridine phosphoramidites. We demonstrate that oligodeoxyribonucleotides modified with the corresponding monomers display (a) minimally decreased thermal affinity toward DNA/RNA complements relative to reference strands, (b) highly robust universal hybridization characteristics (average differences in thermal denaturation temperatures of matched vs mismatched duplexes involving monomer W are <1.7 degrees C), and (c) exceptional affinity toward DNA targets containing abasic sites opposite of the modification site (Delta T-m up to +25 degrees C). The latter observation, along with results from absorption and fluorescence spectroscopy, suggests that the pyrene moiety is intercalating into the duplex whereby the opposing nucleotide is pushed into an extrahelical position. These properties render C2'-pyrene-functionalized triazole-linked DNA as promising universal hybridization probes for applications in nucleic acid chemistry and biotechnology.

  DOI：

  10.1021/jo201845z
• 作为产物：
  描述：

  1-(pyren-1-yl)prop-2-yn-1-ol 在 Jones reagent 、 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 四氢呋喃 、 水 、 丙酮 、 叔丁醇 为溶剂， 反应 7.0h， 生成 5'-O-(4,4'-dimethoxytrityl)-2'-C-[4-(pyrene-1-ylcarbonyl)-1H-1,2,3-triazol-1-yl]-2'-deoxyuridine
  参考文献：
  名称：

  C2′-Pyrene-Functionalized Triazole-Linked DNA: Universal DNA/RNA Hybridization Probes

  摘要：

  Development of universal hybridization probes, that is, oligonudeotides displaying identical affinity toward matched and mismatched DNA/RNA targets, has been a longstanding goal due to potential applications as degenerate PCR primers and microarray probes. The classic approach toward this end has been the use of "universal bases" that either are based on hydrogen-bonding purine derivatives or aromatic base analogues without hydrogen-bonding capabilities. However, development of probes that result in truly universal hybridization without compromising duplex thermostability has proven challenging. Here we have used the "click reaction" to synthesize four C2'-pyrenefunctionalized triazole-linked 2'-deoxyuridine phosphoramidites. We demonstrate that oligodeoxyribonucleotides modified with the corresponding monomers display (a) minimally decreased thermal affinity toward DNA/RNA complements relative to reference strands, (b) highly robust universal hybridization characteristics (average differences in thermal denaturation temperatures of matched vs mismatched duplexes involving monomer W are <1.7 degrees C), and (c) exceptional affinity toward DNA targets containing abasic sites opposite of the modification site (Delta T-m up to +25 degrees C). The latter observation, along with results from absorption and fluorescence spectroscopy, suggests that the pyrene moiety is intercalating into the duplex whereby the opposing nucleotide is pushed into an extrahelical position. These properties render C2'-pyrene-functionalized triazole-linked DNA as promising universal hybridization probes for applications in nucleic acid chemistry and biotechnology.

  DOI：

  10.1021/jo201845z

文献信息

• EMBODIMENTS OF A PROBE AND METHOD FOR TARGETING NUCLEIC ACIDS
  申请人：Hrdlicka Patrick Jerzy

  公开号：US20140220573A1

  公开（公告）日：2014-08-07

  Disclosed embodiments concern a probe comprising one or more pairs of monomers capable of targeting a nucleic acid target. The pair of monomers may be arranged in a manner that promotes thermoinstability of the probe complex, thus producing a probe capable of locating and/or detecting a target. The probe also may comprise one or more natural or non-natural nucleotides capable of Watson-Crick base pairing with an isosequential nucleic acid target. Particular disclosed embodiments concern a method of using the disclosed probe to target nucleic acids. In particular disclosed embodiments, the probe may be incubated with a target nucleic acid and then be detected.

  公开的实施例涉及一种探针，包括一个或多个能够定位到核酸靶标的单体对。这对单体可以被排列在一种促进探针复合物热不稳定性的方式下，从而产生一种能够定位和/或检测靶标的探针。该探针还可以包括一个或多个自然或非自然核苷酸，能够与同构核酸靶标进行Watson-Crick碱基配对。特定的实施例涉及使用所公开的探针来定位核酸的方法。在特定的实施例中，探针可以与靶向核酸一起孵育，然后被检测到。
• US9885082B2
  申请人：——

  公开号：US9885082B2

  公开（公告）日：2018-02-06
• C2′-Pyrene-Functionalized Triazole-Linked DNA: Universal DNA/RNA Hybridization Probes
  作者：Sujay P. Sau、Patrick J. Hrdlicka

  DOI：10.1021/jo201845z

  日期：2012.1.6

  Development of universal hybridization probes, that is, oligonudeotides displaying identical affinity toward matched and mismatched DNA/RNA targets, has been a longstanding goal due to potential applications as degenerate PCR primers and microarray probes. The classic approach toward this end has been the use of "universal bases" that either are based on hydrogen-bonding purine derivatives or aromatic base analogues without hydrogen-bonding capabilities. However, development of probes that result in truly universal hybridization without compromising duplex thermostability has proven challenging. Here we have used the "click reaction" to synthesize four C2'-pyrenefunctionalized triazole-linked 2'-deoxyuridine phosphoramidites. We demonstrate that oligodeoxyribonucleotides modified with the corresponding monomers display (a) minimally decreased thermal affinity toward DNA/RNA complements relative to reference strands, (b) highly robust universal hybridization characteristics (average differences in thermal denaturation temperatures of matched vs mismatched duplexes involving monomer W are <1.7 degrees C), and (c) exceptional affinity toward DNA targets containing abasic sites opposite of the modification site (Delta T-m up to +25 degrees C). The latter observation, along with results from absorption and fluorescence spectroscopy, suggests that the pyrene moiety is intercalating into the duplex whereby the opposing nucleotide is pushed into an extrahelical position. These properties render C2'-pyrene-functionalized triazole-linked DNA as promising universal hybridization probes for applications in nucleic acid chemistry and biotechnology.