1-(3-C-allyl-3,5-di-O-benzyl-β-D-ribo-pentofuranosyl)thymine | 191163-49-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 1-(3-C-allyl-3,5-di-O-benzyl-β-D-ribo-pentofuranosyl)thymine
• 英文别名: 1-(3-Allyl-3,5-di-O-benzyl-beta-D-ribofuranosyl)thymine；1-[(2R,3R,4S,5R)-3-hydroxy-4-phenylmethoxy-5-(phenylmethoxymethyl)-4-prop-2-enyloxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 191163-49-2
• 化学式: C₂₇H₃₀N₂O₆
• 分子量: 478.545
• InChiKey: DSDRRUOGEJNTEH-VJPXLHPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  97.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(3-C-allyl-3,5-di-O-benzyl-β-D-ribo-pentofuranosyl)thymine 在 吡啶 、 sodium hydroxide 、 1,2-thioxane 、 硼烷 、 双氧水 作用下， 生成 3-[(2R,3S,4R,5R)-4-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-3-phenylmethoxy-2-(phenylmethoxymethyl)oxolan-3-yl]propyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  Synthesis and Evaluation of Novel Oligodeoxynucleotides Containing 3′-C-(3-Benzoyloxypropyl)thymidine and Bicyclo Nucleoside Derivatives

  摘要：

  The stereoselective synthesis of 3'-C-Allyluridine derivative 2 has been accomplished. This nucleoside was used as a key synthon for the synthesis of oligodeoxynucleotides containing 3'-C-(3-benzoyloxypropyl)thymidine (X) or bicycle nucleoside (Y+Z) monomers. Preliminary thermal experiments are reported.

  DOI：

  10.1080/07328319708006201
• 作为产物：
  描述：

  1,2-O-isopropylidene-3-C-(prop-1-en-3-yl)-α-D-ribofuranose 在 吡啶 、 N,O-双三甲硅基乙酰胺 、 三氟甲磺酸三甲基硅酯 、 sodium methylate 、 sodium hydride 、 溶剂黄146 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 1-(3-C-allyl-3,5-di-O-benzyl-β-D-ribo-pentofuranosyl)thymine
  参考文献：
  名称：

  A novel class of conformationally restricted oligonucleotide analogues: synthesis of 2′,3′-bridged monomers and RNA-selective hybridisation

  摘要：

  一种新的2′,3′-双环核苷5已被合成并融入寡核苷酸类似物中，从而实现对RNA互补序列的强选择性结合。

  DOI：

  10.1039/a608231i

文献信息

• A novel class of conformationally restricted oligonucleotide analogues: synthesis of 2′,3′-bridged monomers and RNA-selective hybridisation
  作者：Poul Nielsen、Henrik M. Pfundheller、Jesper Wengel

  DOI：10.1039/a608231i

  日期：——

  A novel 2′,3′-bicyclic nucleoside 5 has been synthesised and incorporated into oligonucleotide analogues resulting in strong and selective binding to an RNA complement.

  一种新的2′,3′-双环核苷5已被合成并融入寡核苷酸类似物中，从而实现对RNA互补序列的强选择性结合。
• Synthesis and hybridization properties of β- and α-oligodeoxynucleotides containing β- and α-1-(3-C-allyl-2-deoxy-D-erythro-pentofuranosyl)thymine and α-1-[3-C-(3-aminopropyl)-2-deoxy-D-erythro-pentofuranosyl]thymine
  作者：Pia N. Jørgensen、Ulrik S. Sørensen、Henrik M. Pfundheller、Carl E. Olsen、Jesper Wengel

  DOI：10.1039/a703173d

  日期：——

  Convergent synthesis of β- and α-1-(3-C-allyl-2-deoxy-D-erythro-pentofuranosyl)thymine and their incorporation into β- and α-oligodeoxynucleotides (ODNs) is described. The thermal stabilities of duplexes formed between modified ODNs and complementary single-stranded DNA and RNA have been evaluated. In all cases stable duplexes are formed, but whereas β-ODNs containing β-3′-C-allylthymidine show moderately lowered thermal stability towards both DNA and RNA, α-ODNs containing α-3′-C-allylthymidine show significantly increased thermal stabilities compared with the corresponding β-ODN reference duplexes. Even more stable duplexes towards both DNA and RNA have been obtained using an α-ODN containing one α-1-[3-C-(3-aminopropyl)-2-deoxy-D-erythro-pentofuranosyl]thymine monomer.

  本研究描述了δ-和δ-1-(3-C-烯丙基-2-脱氧-D-赤式戊呋喃糖基)胸腺嘧啶的聚合合成及其与δ-和δ-寡脱氧核苷酸（ODNs）的结合。对修饰的 ODN 与互补的单链 DNA 和 RNA 之间形成的双链体的热稳定性进行了评估。在所有情况下都能形成稳定的双链，但与相应的δ-ODN 参考双链相比，含有δ-3â²-C-烯丙基胸苷的δ-ODN 对 DNA 和 RNA 的热稳定性略有降低，而含有δ-3â²-C-烯丙基胸苷的δ-ODN 的热稳定性则显著提高。使用含有一个δ-1-[3-C-（3-氨基丙基）-2-脱氧-D-赤式戊呋喃糖基]胸腺嘧啶单体的δ-ODN，还能获得对 DNA 和 RNA 都更稳定的双链体。
• 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。