(1S,3R,4S,7R)-7-benzyloxy-1-methanesulfonyloxymethyl-3-(uracil-1-yl)-2,5-dioxabicyclo[2.2.1]heptane | 1275611-08-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,3R,4S,7R)-7-benzyloxy-1-methanesulfonyloxymethyl-3-(uracil-1-yl)-2,5-dioxabicyclo[2.2.1]heptane
• 英文别名: 1-(3-O-benzyl-5-O-methanesulfonyl-2-O,4-C-methylene-α-L-ribofuranosyl)uracil；[(1S,3R,4S,7R)-3-(2,4-dioxopyrimidin-1-yl)-7-phenylmethoxy-2,5-dioxabicyclo[2.2.1]heptan-1-yl]methyl methanesulfonate
• CAS: 1275611-08-9
• 化学式: C₁₈H₂₀N₂O₈S
• 分子量: 424.431
• InChiKey: GZIHFWLUFRHQQD-LHHMISFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  129
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (1S,3R,4S,7R)-7-benzyloxy-1-methanesulfonyloxymethyl-3-(uracil-1-yl)-2,5-dioxabicyclo[2.2.1]heptane 在 氨 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 34.0h， 生成 (1R,3R,4S,7R)-7-benzyloxy-1-hydroxymethyl-3-(uracil-1-yl)-2,5-dioxabicyclo[2.2.1]heptane
  参考文献：
  名称：

  [EN] NUCLEOBASE-FUNCTIONALIZED CONFORMATIONALLY RESTRICTED NUCLEOTIDES AND OLIGONUCLEOTIDES FOR TARGETING NUCLEIC ACIDS
  [FR] NUCLÉOTIDES ET OLIGONUCLÉOTIDES À CONFORMATION RESTREINTE À FONCTIONNALITÉ NUCLÉOBASE POUR CIBLER DES ACIDES NUCLÉIQUES

  摘要：

  公开号：

  WO2011032034A3
• 作为产物：
  描述：

  1-[3-O-benzyl-5-O-(methanesulfonyl)-4-C-(methanesulfonyloxymethyl)-α-L-threo-pentofuranosyl]uracil 在 吡啶 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 8.0h， 生成 (1S,3R,4S,7R)-7-benzyloxy-1-methanesulfonyloxymethyl-3-(uracil-1-yl)-2,5-dioxabicyclo[2.2.1]heptane
  参考文献：
  名称：

  C5-Alkynyl-Functionalized α-L-LNA: Synthesis, Thermal Denaturation Experiments and Enzymatic Stability

  摘要：

  Major efforts are currently being devoted to improving the binding affinity, target specificity, and enzymatic stability of oligonucleotides used for nucleic acid targeting applications in molecular biology, biotechnology, and medicinal chemistry. One of the most popular strategies toward this end has been to introduce additional modifications to the sugar ring of affinity-inducing conformationally restricted nucleotide building blocks such as locked nucleic acid (LNA). In the preceding article in this issue, we introduced a different strategy toward this end, i.e., C5-functionalization of LNA uridines. In the present article, we extend this strategy to alpha-L-LNA: i.e., one of the most interesting diastereomers of LNA. alpha-L-LNA uridine monomers that are conjugated to small C5-alkynyl substituents induce significant improvements in target affinity, binding specificity, and enzymatic stability relative to conventional alpha-L-LNA. The results from the back-to-back articles therefore suggest that C5-functionalization of pyrimidines is a general and synthetically straightforward approach to modulate biophysical properties of oligonucleotides modified with LNA or other conformationally restricted monomers.

  DOI：

  10.1021/jo5006153

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：WO2011032034A3

  公开（公告）日：2011-07-21