Toluene-4-sulfonic acid (3aS,4S,6R,6aR)-6-(6-benzoylamino-purin-9-yl)-4-hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester | 209968-89-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: Toluene-4-sulfonic acid (3aS,4S,6R,6aR)-6-(6-benzoylamino-purin-9-yl)-4-hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester
• 英文别名: [(3aS,4S,6R,6aR)-6-(6-benzamidopurin-9-yl)-4-(hydroxymethyl)-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-yl]methyl 4-methylbenzenesulfonate
• CAS: 209968-89-8
• 化学式: C₂₈H₂₉N₅O₈S
• 分子量: 595.633
• InChiKey: GLFMOBVIDDOZHI-FKTURHEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  42
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  172
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  Toluene-4-sulfonic acid (3aS,4S,6R,6aR)-6-(6-benzoylamino-purin-9-yl)-4-hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester 在 吡啶 、 sodium hydride 、 triethylamine tris(hydrogen fluoride) 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 生成 (1S,3R,4R,7S)-3-(6-N-benzoyladenine-9-yl)-7-hydroxy-1-hydroxymethyl-2,5-dioxabicyclo[2.2.1]heptane
  参考文献：
  名称：

  LNA [2.2.1]双环核苷的新型便捷合成方法

  摘要：

  LNA（锁定核酸）是一种新型的寡核苷酸类似物，含有[2.2.1]双环核苷单体。描述了一种新颖且显着改进的方法，该方法使用4-C-甲苯磺酰氧基甲基-1，2-二-O-乙酰基呋喃糖作为关键合成子，聚合合成LNA [2.2.1]双环核苷。此外，介绍了一种替代的，稳健的线性方法，该方法允许通过三环核苷中间体选择性形成所需的[2.2.1]双环LNA核苷。

  DOI：

  10.1016/s0040-4039(98)00706-0
• 作为产物：
  描述：

  N⁶-benzoyl-5'-hydroxymethyl-O^2'_,O3'-isopropylidene-adenosine 、 对甲苯磺酰氯 在 吡啶 作用下， 反应 4.0h， 以13%的产率得到Toluene-4-sulfonic acid (3aS,4R,6R,6aR)-6-(6-benzoylamino-purin-9-yl)-4-hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester
  参考文献：
  名称：

  LNA [2.2.1]双环核苷的新型便捷合成方法

  摘要：

  LNA（锁定核酸）是一种新型的寡核苷酸类似物，含有[2.2.1]双环核苷单体。描述了一种新颖且显着改进的方法，该方法使用4-C-甲苯磺酰氧基甲基-1，2-二-O-乙酰基呋喃糖作为关键合成子，聚合合成LNA [2.2.1]双环核苷。此外，介绍了一种替代的，稳健的线性方法，该方法允许通过三环核苷中间体选择性形成所需的[2.2.1]双环LNA核苷。

  DOI：

  10.1016/s0040-4039(98)00706-0

文献信息

• 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。
• Bi- and tri-cyclic nucleoside, nucleotide and oligonucleoide analogues
  申请人：Exiqon A/S

  公开号：EP2253639A1

  公开（公告）日：2010-11-24

  The present application discloses a kit for the isolation, purification, amplification, detection, identification, quantification, or capture of natural or synthetic nucleic acids, the kit comprising a reaction body and LNA modified oligonucleotide(s) (oligomers) or locked nucleoside analogue(s) (LNAs), in which the oligomers/LNAs optionally are immobilised onto said reactions body. The application further discloses corresponding uses, e.g. for capture and detection of nucleic acids such as RNA or DNA; as a probe in in-situ, Southern, Dot blot, reverse Dot blot, and Northern hybridisations; in the construction of an affinity pair; as a primer in a nucleic acid sequencing reaction or primer extension reactions; as an aptamer; for the labelling of cells; to hybridise to non-protein coding cellular RNAs, such as tRNA, rRNA, snRNA and scRNA, in vivo or in-vitro; in the construction of an oligonucleotide containing a fluorophor and a quencher; or in the construction of Taqman probes or Molecular Beacons.

  本申请公开了一种用于天然或合成核酸的分离、纯化、扩增、检测、鉴定、定量或捕获的试剂盒，该试剂盒包括反应体和 LNA 修饰的寡核苷酸（寡聚体）或锁定的核苷类似物（LNA），其中寡聚体/LNA 可选择性地固定在所述反应体上。该申请还披露了相应的用途，例如用于捕获和检测核酸，如 RNA 或 DNA；作为原位杂交、Southern 杂交、点印迹杂交、反向点印迹杂交和 Northern 杂交中的探针；用于构建亲和对；作为核酸测序反应或引物延伸反应中的引物；作为适配体；用于细胞标记；在体内或体外与非蛋白编码细胞 RNA 杂交，如 tRNA、rRNA、snRNA 和 scRNA；用于构建含有荧光素和淬灭剂的寡核苷酸；或用于构建 Taqman 探针或分子信标。