1',2'-dideoxy-β-1'-(2,4-dichloro-5-methylphenyl)-D-ribofuranose | 798552-93-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1',2'-dideoxy-β-1'-(2,4-dichloro-5-methylphenyl)-D-ribofuranose
• 英文别名: 1',2'-dideoxy-1'-(2,4-dichloro-5-methylphenyl)-β-D-ribofuranose；(2R,3S,5R)-5-(2,4-dichloro-5-methylphenyl)-2-(hydroxymethyl)oxolan-3-ol
• CAS: 798552-93-9
• 化学式: C₁₂H₁₄Cl₂O₃
• 分子量: 277.147
• InChiKey: VGSLYTSEZPNCIF-QJPTWQEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1',2'-dideoxy-β-1'-(2,4-dichloro-5-methylphenyl)-D-ribofuranose 在 human thymidine kinase 2 、 5’-三磷酸腺苷 作用下， 生成
  参考文献：
  名称：

  Jarchow-Choy, Sarah K.; Sjuvarsson, Elena; Sintim, Herman O., Journal of the American Chemical Society, 2009, vol. 131, p. 5488 - 5494

  摘要：

  DOI：
• 作为产物：
  描述：

  1-溴-2,4-二氯-5-甲基苯 在 正丁基锂 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 6.0h， 生成 1',2'-dideoxy-β-1'-(2,4-dichloro-5-methylphenyl)-D-ribofuranose
  参考文献：
  名称：

  A Set of Nonpolar Thymidine Nucleoside Analogues with Gradually Increasing Size

  摘要：

  [GRAPHICS]We describe a series of nonpolar nucleoside analogues having similar shapes and gradually increasing size. The structure of the nucleobase thymine was mimicked with toluene derivatives, replacing O2/O4 with hydrogen, fluorine, chlorine, bromine, and iodine. Glycosidic bonds were formed by reactions of lithiated 2,4-dihalotoluenes with a deoxyribonolactone derivative. Structural analysis by NMR showed similar conformations across the series. The compounds are useful for study of the biological recognition of nucleotides and nucleic acids.

  DOI：

  10.1021/ol048487u

文献信息

• A Series of Nonpolar Thymidine Analogues of Increasing Size:  DNA Base Pairing and Stacking Properties
  作者：Tae Woo Kim、Eric T. Kool

  DOI：10.1021/jo048061t

  日期：2005.3.1

  [GRAPHICS]We describe the properties in DNA of a set of five nonpolar nucleoside mimics in which shape is similar but size is increased gradually. The compounds vary in the size of their exocyclic substituents, which range from hydrogen to iodine, and are designed to test the steric effects of nucleosides, nucleotides, and DNA in biological systems in a systematic way. We describe the conversion of toluene, 2,4-difluorotoluene, 2,4-dichlorotoluene, 2,4-dibromotoluene, and 2,4-diiodotoluene deoxyribosides into suitably protected phosphoramidite derivatives and their incorporation into synthetic DNAs. Studies of their behavior in the context of hexamer and dodecamer duplexes were carried out, with comparison to natural thymine. Thermal melting data with compounds in 5' dangling positions showed that all five compounds stack more strongly than thymine, and all the dihalo-substituted cases stack more strongly than the unsubstituted toluene case. Stacking correlated with surface area and hydrophobicity, both of which increase across the series. In base-pairing studies, all five compounds showed destabilized pairing opposite natural bases (relative to thymine-adenine pairing), as expected. Notably, pairing among the nonpolar base analogues was considerably more stable, and some of the pairs involving the largest analogues showed stability equal to that of a natural thymine-adenine pair. The results establish the base pairing properties of a potentially useful new series of biochemical probes for DNA-protein interactions and also identify a set of new, stable hydrophobic base pairs for designed genetic pairing systems.
• A Set of Nonpolar Thymidine Nucleoside Analogues with Gradually Increasing Size
  作者：Tae Woo Kim、Eric T. Kool

  DOI：10.1021/ol048487u

  日期：2004.10.1

  [GRAPHICS]We describe a series of nonpolar nucleoside analogues having similar shapes and gradually increasing size. The structure of the nucleobase thymine was mimicked with toluene derivatives, replacing O2/O4 with hydrogen, fluorine, chlorine, bromine, and iodine. Glycosidic bonds were formed by reactions of lithiated 2,4-dihalotoluenes with a deoxyribonolactone derivative. Structural analysis by NMR showed similar conformations across the series. The compounds are useful for study of the biological recognition of nucleotides and nucleic acids.
• Jarchow-Choy, Sarah K.; Sjuvarsson, Elena; Sintim, Herman O., Journal of the American Chemical Society, 2009, vol. 131, p. 5488 - 5494
  作者：Jarchow-Choy, Sarah K.、Sjuvarsson, Elena、Sintim, Herman O.、Eriksson, Staffan、Kool, Eric T.

  DOI：——

  日期：——