5-[3-(1-pyrenecarboxamido)propynyl]-2'-deoxyuridine

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 5-[3-(1-pyrenecarboxamido)propynyl]-2'-deoxyuridine
• 英文别名: N-[3-[1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,4-dioxopyrimidin-5-yl]prop-2-ynyl]pyrene-1-carboxamide
• 化学式: C₂₉H₂₃N₃O₆
• 分子量: 509.518
• InChiKey: AMVXJDNRAVCKGS-RBZQAINGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  38
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  128
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-芘甲酸 在 copper(l) iodide 、 四(三苯基膦)钯 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氯乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.83h， 生成 5-[3-(1-pyrenecarboxamido)propynyl]-2'-deoxyuridine
  参考文献：
  名称：

  Pyrene-Labeled Base-Discriminating Fluorescent DNA Probes for Homogeneous SNP Typing

  摘要：

  This paper describes the design of novel base-discriminating fluorescent (BDF) nucleobases and their application to single nucleotide polymorphism (SNP) typing. We devised novel BDF nucleosides, U-Py and C-Py, which contain a pyrenecarboxamide chromophore connected by a propargyl linker. The fluorescence spectrum of the duplex containing a U-Py/A base pair showed a strong emission at 397 nm on 327 nm excitation. In contrast, the fluorescence of duplexes containing U-Py/N base pairs (N = C, G, or T) was considerably weaker. The proposed structure of the duplex containing a matched U-Py/A base pair suggests that the high polarity near the pyrenecarboxamide group is responsible for the strong A-selective fluorescence emission. Moreover, the fluorescence of the duplex containing a U-Py/A base pair was not quenched by a flanking C/G base pair. The fluorescence properties are quite different from previous BDF nucleobases, where fluorescence is quenchable by flanking C/G base pairs. The duplex containing the C derivative, C-Py, selectively emitted fluorescence when the base opposite C-Py was G. The drastic change of fluorescence intensity by the nature of the complementary base is extremely useful for SNP typing. U-Py- and C-Py-containing oligodeoxynucleotides acted as effective reporter probes for homogeneous SNP typing of DNA samples containing c-Ha-ras and BRCA2 SNP sites.

  DOI：

  10.1021/ja039625y

文献信息

• NUCLEOBASE-FUNCTIONALIZED CONFORMATIONALLY RESTRICTED NUCLEOTIDES AND OLIGONUCLEOTIDES FOR TARGETING OF NUCLEIC ACIDS
  申请人：Hrdlicka Patrick J.

  公开号：US20120295862A1

  公开（公告）日：2012-11-22

  Embodiments are disclosed herein that involve C5-functionalized nucleic acids, which can be used for detecting a target in a nucleic acid. Particular embodiments disclose methods for making these compounds, wherein the compounds can be formed by coupling of an intermediate with a linker. Certain embodiments disclose the use of these compounds for detecting single nucleotide polymorphisms, and for increasing the thermal affinity of nucleic acid complements as compared to unmodified nucleic acid complements. In addition, the disclosed compounds can decrease enzymatic degradation of nucleic acids.

  本文披露了涉及C5-官能化核酸的实施例，可用于检测核酸中的目标。特定实施例披露了制备这些化合物的方法，其中化合物可以通过中间体与连接剂的偶联形成。某些实施例披露了使用这些化合物检测单核苷酸多态性，并将其与未经修饰的核酸互补物相比增加了热亲和力。此外，披露的化合物可以减少核酸的酶降解。
• NUCLEOBASE-FUNCTIONALIZED CONFORMATIONALLY RESTRICTED NUCLEOTIDES AND OLIGONUCLEOTIDES FOR TARGETING NUCLEIC ACIDS
  申请人：Hrdlicka Patrick Jerzy

  公开号：US20130337581A1

  公开（公告）日：2013-12-19

  Embodiments are disclosed herein that involve C5-functionalized nucleic acids, which can be used for detecting a target in a nucleic acid. Particular embodiments disclose methods for making these compounds, wherein the compounds can be formed by coupling of an intermediate with a linker. Certain embodiments disclose the use of these compounds for detecting single nucleotide polymorphisms, and for increasing the thermal affinity of nucleic acid complements as compared to unmodified nucleic acid complements. In addition, the disclosed compounds can decrease enzymatic degradation of nucleic acids.
• US8518908B2
  申请人：——

  公开号：US8518908B2

  公开（公告）日：2013-08-27
• US8912318B2
  申请人：——

  公开号：US8912318B2

  公开（公告）日：2014-12-16
• [EN] NUCLEOBASE-FUNCTIONALIZED CONFORMATIONALLY RESTRICTED NUCLEOTIDES AND OLIGONUCLEOTIDES FOR TARGETING NUCLEIC ACIDS<br/>[FR] NUCLÉOTIDES ET OLIGONUCLÉOTIDES À CONFORMATION RESTREINTE À FONCTIONNALITÉ NUCLÉOBASE POUR CIBLER DES ACIDES NUCLÉIQUES
  申请人：UNIV IDAHO

  公开号：WO2011032034A2

  公开（公告）日：2011-03-17

  Embodiments are disclosed herein that involve C5-functionalized nucleic acids, which can be used for detecting a target in a nucleic acid. Particular embodiments disclose methods for making these compounds, wherein the compounds can be formed by coupling of an intermediate with a linker. Certain embodiments disclose the use of these compounds for detecting single nucleotide polymorphisms, and for increasing the thermal affinity of nucleic acid complements as compared to unmodified nucleic acid complements. In addition, the disclosed compounds can decrease enzymatic degradation of nucleic acids.