1-(α-L-ribofuranosyl)thymine | 433934-30-6

• 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-(α-L-ribofuranosyl)thymine
• 英文别名: 5-methyl-3-α-L-ribofuranosyl-1H-pyrimidine-2,4-dione；alpha-l-Ribofuranosyl thymine；1-[(2R,3S,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 433934-30-6
• 化学式: C₁₀H₁₄N₂O₆
• 分子量: 258.231
• InChiKey: DWRXFEITVBNRMK-BMLSCUAFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  119
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(α-L-ribofuranosyl)thymine 在 吡啶 、 咪唑 作用下， 生成 1-[(2R,3S,4R,5S)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  α-l-RNA (α-l-ribo Configured RNA): Synthesis and RNA-Selective Hybridization of α-l-RNA/α-l-LNA Chimera

  摘要：

  Synthesis of the novel a-L-ribofuranosyl phosphoramidite derivative 7 was accomplished via the alpha-L-ribofuranosyl thymine nucleoside 4. Amidite 7 was used in automated syntheses of chimeric oligonucleotides composed of mixtures of the novel alpha-L-RNA nucleotide monomer (T-alphaL, alpha-L-ribo configured RNA), and DNA, LNA (T-L, locked nucleic acid) or alpha-L-LNA (T-alphaL(T), alpha-L-ribo configured locked nucleic acid) nucleotide monomers. For alpha-L-RNA/DNA and alpha-L-RNA/alpha-L-LNA chimeras, RNA-selective hybridization was obtained, for alpha-L-RNA/alpha-L-LNA chimera we found increased binding affinity compared to the corresponding DNA:RNA reference duplex. In addition, alpha-L-RNA/alpha-L-LNA chimera displayed significant stabilization towards 3'-exonucleolytic degradation. These, results indicate that alpha-L-RNA/alpha-L-LNA chimeras deserve further evaluation as antisense molecules. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00807-1
• 作为产物：
  描述：

  1-<3',5'-O-(1,1,3,3-Tetraisopropyldisiloxane-1,3-diyl)-α-L-arabinofuranosyl>thymine 在 吡啶 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 18.0h， 生成 1-(α-L-ribofuranosyl)thymine
  参考文献：
  名称：

  α-l-RNA (α-l-ribo Configured RNA): Synthesis and RNA-Selective Hybridization of α-l-RNA/α-l-LNA Chimera

  摘要：

  Synthesis of the novel a-L-ribofuranosyl phosphoramidite derivative 7 was accomplished via the alpha-L-ribofuranosyl thymine nucleoside 4. Amidite 7 was used in automated syntheses of chimeric oligonucleotides composed of mixtures of the novel alpha-L-RNA nucleotide monomer (T-alphaL, alpha-L-ribo configured RNA), and DNA, LNA (T-L, locked nucleic acid) or alpha-L-LNA (T-alphaL(T), alpha-L-ribo configured locked nucleic acid) nucleotide monomers. For alpha-L-RNA/DNA and alpha-L-RNA/alpha-L-LNA chimeras, RNA-selective hybridization was obtained, for alpha-L-RNA/alpha-L-LNA chimera we found increased binding affinity compared to the corresponding DNA:RNA reference duplex. In addition, alpha-L-RNA/alpha-L-LNA chimera displayed significant stabilization towards 3'-exonucleolytic degradation. These, results indicate that alpha-L-RNA/alpha-L-LNA chimeras deserve further evaluation as antisense molecules. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00807-1

文献信息

• [EN] OLIGONUCLEOTIDES MODIFIED WITH NOVEL alpha -L-RNA ANALOGUES<br/>[FR] OLIGONUCLEOTIDES MODIFIES A L'AIDE DE NOUVEAUX ANALOGUES D'ARN-L-ALPHA
  申请人：EXIQON AS

  公开号：WO2003039523A2

  公开（公告）日：2003-05-15

  The invention relates to novel α-L-RNA monomers, which, when incorporated into an oligonucleotide impair a higher tendency towards hybridization with a RNA complement, as comparred to a DNA complement. The invention also relates to a process for the preparation of an α-L-RNA modified oligonucleotide and an intermediate for manufacturing the same. The novel oligonucleotides are useful for a variety of therapeautic, diagnostic, and general molecular biology applications.
• α-l-RNA (α-l-ribo Configured RNA): Synthesis and RNA-Selective Hybridization of α-l-RNA/α-l-LNA Chimera
  作者：Lise Keinicke、Mads D. Sørensen、Jesper Wengel

  DOI：10.1016/s0960-894x(01)00807-1

  日期：2002.2

  Synthesis of the novel a-L-ribofuranosyl phosphoramidite derivative 7 was accomplished via the alpha-L-ribofuranosyl thymine nucleoside 4. Amidite 7 was used in automated syntheses of chimeric oligonucleotides composed of mixtures of the novel alpha-L-RNA nucleotide monomer (T-alphaL, alpha-L-ribo configured RNA), and DNA, LNA (T-L, locked nucleic acid) or alpha-L-LNA (T-alphaL(T), alpha-L-ribo configured locked nucleic acid) nucleotide monomers. For alpha-L-RNA/DNA and alpha-L-RNA/alpha-L-LNA chimeras, RNA-selective hybridization was obtained, for alpha-L-RNA/alpha-L-LNA chimera we found increased binding affinity compared to the corresponding DNA:RNA reference duplex. In addition, alpha-L-RNA/alpha-L-LNA chimera displayed significant stabilization towards 3'-exonucleolytic degradation. These, results indicate that alpha-L-RNA/alpha-L-LNA chimeras deserve further evaluation as antisense molecules. (C) 2002 Elsevier Science Ltd. All rights reserved.