1'-β-D-[8-(6-methylquinazoline-2,4-dione)]-2'-deoxyribofuranose | 639465-38-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1'-β-D-[8-(6-methylquinazoline-2,4-dione)]-2'-deoxyribofuranose
• 英文别名: 8-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-methyl-1H-quinazoline-2,4-dione
• CAS: 639465-38-6
• 化学式: C₁₄H₁₆N₂O₅
• 分子量: 292.291
• InChiKey: IGGWJAKHCFLGPA-HBNTYKKESA-N

物化性质

• 密度：
  1.407±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  108
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1'-β-D-[8-(6-methylquinazoline-2,4-dione)]-2'-deoxyribofuranose 在 吡啶 、 tetraphosphorus decasulfide 、 氨 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 29.0h， 生成 Diisopropyl-phosphoramidous acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-[4-(dimethylamino-methyleneamino)-6-methyl-2-oxo-1,2-dihydro-quinazolin-8-yl]-tetrahydro-furan-3-yl ester 2-cyano-ethyl 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
• 作为产物：
  描述：

  1-β-D-[8-(2,4-dimethoxy-6-methylquinazoline)]-2'-deoxyribofuranose 在 溶剂黄146 、 sodium iodide 作用下， 反应 0.75h， 以100%的产率得到1'-β-D-[8-(6-methylquinazoline-2,4-dione)]-2'-deoxyribofuranose
  参考文献：
  名称：

  Toward a New Genetic System with Expanded Dimensions:  Size-Expanded Analogues of Deoxyadenosine and Thymidine

  摘要：

  We describe the design, preparation, and properties of two key building blocks of a size-expanded genetic system. Nucleoside analogues of the natural nucleosides dA and dT are reported in which the fusion of a benzo ring increases their size by ca. 2.4 Angstrom. The expanded dA analogue (dxA), having a tricyclic base, was first reported by Leonard nearly three decades ago. We describe a shortened and more efficient approach to this compound. The expanded dT analogue (dxT), a methylquinazolinedione C-glycoside, was previously unknown; we describe its preparation in eight steps from 5-methylanthranilic acid. The key glycoside bond formation employed Pd-mediated coupling of an aryl iodide precursor with a dihydrofuran derivative of deoxyribose. Both nucleosides are shown to be efficient fluorophores, emitting light in the blue-violet range. The base-protected phosphoramidite derivatives were prepared, and short oligonucleotides containing them were characterized. The two size-expanded nuclecisides are key components of a new four-base genetic system designed to form helical paired structures having a diameter greater than that of natural DNA. Elements of the design of this expanded genetic molecule, termed xDNA, are discussed, including the possibility of up to eight base pairs of information storage capability.

  DOI：

  10.1021/ja038384r