(1S,3S,4R,7S)-7-hydroxy-1-hydroxymethyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane | 219854-53-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,3S,4R,7S)-7-hydroxy-1-hydroxymethyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane
• 英文别名: 1-[(1S,3S,4R,7S)-7-hydroxy-1-(hydroxymethyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl]-5-methylpyrimidine-2,4-dione
• CAS: 219854-53-2
• 化学式: C₁₁H₁₄N₂O₆
• 分子量: 270.242
• InChiKey: TYYUAZVXLRMUMN-UAPOJFLHSA-N

物化性质

• 密度：
  1.598±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  108
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1S,3S,4R,7S)-7-hydroxy-1-hydroxymethyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 ammonium hydroxide 、 silver nitrate 、 三氯氧磷 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 201.25h， 生成 (1R,3S,4R,7S)-3-(4-N-benzoyl-5-methylcytosin-1-yl)-7-(tert-butyldimethylsilyl)oxy-1-(4,4'-dimethoxytrityl)oxymethyl-2,5-dioxabicyclo[2.2.1]heptane
  参考文献：
  名称：

  α-LNA (Locked Nucleic Acid withα-D-Configuration): Synthesis and Selective Parallel Recognition of RNA

  摘要：

  alpha-LNA is presented as a stereoisomer of LNA (locked nucleic acid) with alpha-D-configuration. Three different approaches towards the thymine a-LNA monomer as well as the 5-methylcytosine alpha-LNA monomer are presented. Different alpha-LNA sequences have been synthesised and their hybridisation with complementary DNA and RNA has been evaluated by means of thermal stability experiments and circular dichroism spectroscopy. In a mixed pyrimidine sequence, alpha-LNA displays unprecedented parallel-stranded and selective RNA binding. Furthermore, a remarkable selectivity for hybridisation with RNA over DNA is indicated.

  DOI：

  10.1002/1521-3765(20020201)8:3<712::aid-chem712>3.0.co;2-0
• 作为产物：
  描述：

  胸腺嘧啶 在 palladium dihydroxide 三甲基氯硅烷 、 氢气 、 sodium hydride 、 N,N-二(三甲基硅基)乙酰胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 168.0h， 生成 (1S,3S,4R,7S)-7-hydroxy-1-hydroxymethyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane
  参考文献：
  名称：

  α-LNA, locked nucleic acid with α-d-configuration

  摘要：

  有效合成了α-LNA的双环胸腺嘧啶单体（αTL），并用于合成α-LNA序列：在α-配置的寡胸腺苷酸中加入单个αTL单体会降低对互补DNA和RNA的亲和力，而完全改性的α-LNA序列对互补RNA表现出非常高效的识别能力。

  DOI：

  10.1039/b003104f

文献信息

• Synthesis and chemoselective activation of phenyl 3,5-di-O-benzyl-2-O,4-C-methylene-1-thio-β-d-ribofuranoside: a key synthon towards α-LNA
  作者：Poul Nielsen、Jesper Wengel

  DOI：10.1039/a806817h

  日期：——

  A bicyclic thiofuranoside (phenyl 3,5-di-O-benzyl-2-O,4-C-methylene-β-D-ribofuranoside) was efficiently synthesized and introduced as the key synthon in a method for convergent synthesis of α- and β-LNA nucleosides; acid-induced ring-opening reactions of the corresponding bicyclic methyl furanoside are also described.

  一种双环硫呋喃苷（苯基3,5-二-O-苄基-2-O,4-C-亚甲基-β-D-核糖呋喃苷）被高效合成并作为α-和β-LNA核苷的聚合合成中的关键合成物引入；还描述了相应双环甲基呋喃苷的酸诱导开环反应。
• Oligonucleotide analogues
  申请人：Wengel Jesper

  公开号：US20050287566A1

  公开（公告）日：2005-12-29

  The present invention relates to novel bicyclic and tricyclic nucleoside and nucleotide analogues as well as to oligonucleotides comprising such elements. The nucleotide analogues, LNAs (Locked Nucleoside Analogues), are able to provide valuable improvements to oligonucleotides with respect to affinity and specificity towards complementary RNA and DNA oligomers. The novel type of LNA modified oligonucleotides, as well as the LNAs as such, are useful in a wide range of diagnostic applications as well as therapeutic applications. Among these can be mentioned antisense applications, PCR applications, strand displacement oligomers, as substrates for nucleic acid polymerases, as nucleotide based drugs, etc. The present invention also relates to such applications.

  本发明涉及新型的双环和三环核苷酸和核苷酸类似物，以及包含这些元素的寡核苷酸。这些核苷酸类似物，即锁定核苷酸类似物（LNAs），能够为寡核苷酸提供与互补RNA和DNA寡聚物的亲和力和特异性方面的有价值的改进。这种新型的LNA修饰的寡核苷酸以及LNA本身在广泛的诊断应用和治疗应用中非常有用。其中包括反义应用、PCR应用、链置换寡聚物、作为核酸聚合酶的底物、作为基于核苷酸的药物等。本发明还涉及这些应用。
• OLIGONUCLEOTIDE ANALOGUES
  申请人：Wengel Jesper

  公开号：US20100279895A1

  公开（公告）日：2010-11-04

  The present invention relates to novel bicyclic and tricyclic nucleoside and nucleotide analogues as well as to oligonucleotides comprising such elements. The nucleotide analogues, LNAs (Locked Nucleoside Analogues), are able to provide valuable improvements to oligonucleotides with respect to affinity and specificity towards complementary RNA and DNA oligomers. The novel type of LNA modified oligonucleotides, as well as the LNAs as such, are useful in a wide range of diagnostic applications as well as therapeutic applications. Among these can be mentioned antisense applications, PCR applications, strand displacement oligomers, as substrates for nucleic acid polymerases, as nucleotide based drugs, etc. The present invention also relates to such applications.

  本发明涉及新型的双环和三环核苷酸和核苷酸类似物，以及包含这些元素的寡核苷酸。这些核苷酸类似物，即LNAs（锁定核苷酸类似物），能够为寡核苷酸提供与互补RNA和DNA寡聚物相比亲和力和特异性的有价值的改进。这种新型的LNA修饰的寡核苷酸以及LNAs本身在广泛的诊断应用和治疗应用中都有用途。其中可以提到反义应用、PCR应用、链位移寡聚物、作为核酸聚合酶底物、作为核苷酸基药物等。本发明还涉及这些应用。
• Oligonucleotide Analogues
  申请人：WENGEL Jesper

  公开号：US20110245327A1

  公开（公告）日：2011-10-06

  The present invention relates to novel bicyclic and tricyclic nucleoside and nucleotide analogues as well as to oligonucleotides comprising such elements. The nucleotide analogues, LNAs ( L ocked N ucleoside A nalogues), are able to provide valuable improvements to oligonucleotides with respect to affinity and specificity towards complementary RNA and DNA oligomers. The novel type of LNA modified oligonucleotides, as well as the LNAs as such, are useful in a wide range of diagnostic applications as well as therapeutic applications. Among these can be mentioned antisense applications, PCR applications, strand displacement oligomers, as substrates for nucleic acid polymerases, as nucleotide based drugs, etc. The present invention also relates to such applications.

  本发明涉及新型的双环和三环核苷酸和核苷酸类似物，以及包含这些元素的寡核苷酸。核苷酸类似物，即锁定核苷酸类似物（LNAs），能够为寡核苷酸提供有价值的改进，使其对互补的RNA和DNA寡聚体具有更高的亲和力和特异性。这种新型的LNA修饰的寡核苷酸以及LNAs本身在广泛的诊断应用和治疗应用中都很有用。其中包括反义应用、PCR应用、链置换寡聚体、作为核酸聚合酶的底物、作为基于核苷酸的药物等。本发明还涉及这些应用。
• Bi-cyclic nucleoside, nucleotide and oligonucleoide analogues
  申请人：Exiqon A/S

  公开号：EP1557424A1

  公开（公告）日：2005-07-27

  The present invention relates to novel bicyclic and tricyclic nucleoside analogues as well as to oligonucleotides comprising such elements. The nucleotide analogues, LNAs (Locked Nucleoside Analogues), are able to provide valuable improvements to oligonucleotides with respect to affinity and specificity towards complementary RNA and DNA oligomers. The novel type of LNA modified oligonucleotides, as well as the LNAs as such, are useful in a wide range of diagnostic applications as well as therapeutic applications. Among these can be mentioned antisense applications, PCR applications, strand displacement oligomers, as substrates for nucleic acid polymerises, as nucleotide based drugs, etc. The present invention also relates to such applications.

  本发明涉及新型双环和三环核苷类似物以及包含此类元素的寡核苷酸。这种核苷酸类似物 LNA（锁定核苷酸类似物）能够在对互补 RNA 和 DNA 寡聚体的亲和性和特异性方面对寡核苷酸进行有价值的改进。新型 LNA 修饰寡核苷酸以及 LNA 本身可用于广泛的诊断和治疗应用。其中包括反义应用、PCR 应用、链置换寡聚体、核酸聚合底物、核苷酸类药物等。本发明也涉及此类应用。