1',2'-dideoxy-β-1'-(2,4-dibromo-5-methylphenyl)-5'-O-(4,4'-dimethoxytrityl)-D-ribofuranose | 849675-14-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 1',2'-dideoxy-β-1'-(2,4-dibromo-5-methylphenyl)-5'-O-(4,4'-dimethoxytrityl)-D-ribofuranose
• 英文别名: (2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(2,4-dibromo-5-methylphenyl)oxolan-3-ol
• CAS: 849675-14-5
• 化学式: C₃₃H₃₂Br₂O₅
• 分子量: 668.422
• InChiKey: GWKVWPXHBLNGDZ-DCMFLLSESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-氰乙基N,N-二异丙基氯亚磷酰胺 、 1',2'-dideoxy-β-1'-(2,4-dibromo-5-methylphenyl)-5'-O-(4,4'-dimethoxytrityl)-D-ribofuranose 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 1',2'-dideoxy-β-1'-(2,4-dibromo-5-methylphenyl)-5'-O-(4,4'-dimethoxytrityl)-D-ribofuranose 2-cyanoethyl N,N-diisopropylphosphoramidite
  参考文献：
  名称：

  A Series of Nonpolar Thymidine Analogues of Increasing Size:  DNA Base Pairing and Stacking Properties

  摘要：

  [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.

  DOI：

  10.1021/jo048061t
• 作为产物：
  描述：

  4,4'-双甲氧基三苯甲基氯 、 1',2'-dideoxy-β-1'-(2,4-dibromo-5-methylphenyl)-D-ribofuranose 在 吡啶 、 N,N-二异丙基乙胺 作用下， 反应 3.0h， 生成 1',2'-dideoxy-β-1'-(2,4-dibromo-5-methylphenyl)-5'-O-(4,4'-dimethoxytrityl)-D-ribofuranose
  参考文献：
  名称：

  A Series of Nonpolar Thymidine Analogues of Increasing Size:  DNA Base Pairing and Stacking Properties

  摘要：

  [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.

  DOI：

  10.1021/jo048061t

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.