Acetic acid (2R,3S,5R)-2-acetoxymethyl-5-(6-methyl-2-oxo-4-thioxo-1,2,3,4-tetrahydro-quinazolin-8-yl)-tetrahydro-furan-3-yl ester | 843639-19-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2R,3S,5R)-2-acetoxymethyl-5-(6-methyl-2-oxo-4-thioxo-1,2,3,4-tetrahydro-quinazolin-8-yl)-tetrahydro-furan-3-yl ester
• 英文别名: [(2R,3S,5R)-3-acetyloxy-5-(6-methyl-2-oxo-4-sulfanylidene-1H-quinazolin-8-yl)oxolan-2-yl]methyl acetate
• CAS: 843639-19-0
• 化学式: C₁₈H₂₀N₂O₆S
• 分子量: 392.433
• InChiKey: WPJZGKLHLGYWIM-QLFBSQMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  135
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3S,5R)-2-acetoxymethyl-5-(6-methyl-2-oxo-4-thioxo-1,2,3,4-tetrahydro-quinazolin-8-yl)-tetrahydro-furan-3-yl ester 在 氨 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以97%的产率得到4-Amino-8-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-6-methyl-1H-quinazolin-2-one
  参考文献：
  名称：

  Size-Expanded Analogues of dG and dC:  Synthesis and Pairing Properties in DNA

  摘要：

  We describe the completion of the set of four benzo-fused expanded DNA (xDNA) nucleoside analogues. We previously reported the development of benzo-fused analogues of dA and dT and their inclusion in an exceptionally stable new four-base genetic system. termed xDNA. in which the base pairs were expanded in size. Here we describe the preparation and properties of the-second half of this nucleotide set: namely, the previously unknown dxC and dxG nucleosides. The dxC analogue was prepared from the previously reported dxT nucleoside in three steps and 57%, yield. The large-sized deoxyguanosine analogue was prepared from an intermediate in the synthesis of dxA, yielding dxG in 14 steps overall (2.4%). Suitably protected versions of the deoxynucleosides were prepared for oligonucleotide synthesis following standard procedures, and they were readily incorporated into DNA by automated synthesizer. "Dangling-end" measurements revealed that the benzo-fused homologues stack considerably more strongly on neighbor DNA sequences h do their natural counterparts. Base pairing experiments with xC or xG bases showed that they pair selectively with their Watson-Crick partners, but with mild destabilization. due apparently to their larger size. Overall, the data suggest that the fluorescent xG and xG bases may he useful probes of steric effects in the study of biological nucleotide recognition mechanisms. In addition. the completion of the xDNA nucleoside set makes it possible in the future to construct full four-base xDNA strands that can target any sequence of natural DNA and RNA.

  DOI：

  10.1021/jo048357z
• 作为产物：
  描述：

  1'-β-D-[8-(6-methylquinazoline-2,4-dione)]-2'-deoxyribofuranose 在 吡啶 、 tetraphosphorus decasulfide 作用下， 反应 12.0h， 生成 Acetic acid (2R,3S,5R)-2-acetoxymethyl-5-(6-methyl-2-oxo-4-thioxo-1,2,3,4-tetrahydro-quinazolin-8-yl)-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  Size-Expanded Analogues of dG and dC:  Synthesis and Pairing Properties in DNA

  摘要：

  We describe the completion of the set of four benzo-fused expanded DNA (xDNA) nucleoside analogues. We previously reported the development of benzo-fused analogues of dA and dT and their inclusion in an exceptionally stable new four-base genetic system. termed xDNA. in which the base pairs were expanded in size. Here we describe the preparation and properties of the-second half of this nucleotide set: namely, the previously unknown dxC and dxG nucleosides. The dxC analogue was prepared from the previously reported dxT nucleoside in three steps and 57%, yield. The large-sized deoxyguanosine analogue was prepared from an intermediate in the synthesis of dxA, yielding dxG in 14 steps overall (2.4%). Suitably protected versions of the deoxynucleosides were prepared for oligonucleotide synthesis following standard procedures, and they were readily incorporated into DNA by automated synthesizer. "Dangling-end" measurements revealed that the benzo-fused homologues stack considerably more strongly on neighbor DNA sequences h do their natural counterparts. Base pairing experiments with xC or xG bases showed that they pair selectively with their Watson-Crick partners, but with mild destabilization. due apparently to their larger size. Overall, the data suggest that the fluorescent xG and xG bases may he useful probes of steric effects in the study of biological nucleotide recognition mechanisms. In addition. the completion of the xDNA nucleoside set makes it possible in the future to construct full four-base xDNA strands that can target any sequence of natural DNA and RNA.

  DOI：

  10.1021/jo048357z