7-bromo-1H-naphtho-1,3-oxazine-2,4-dione | 906546-06-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 7-bromo-1H-naphtho-1,3-oxazine-2,4-dione
• 英文别名: 7-bromo-1H-benzo[g][3,1]benzoxazine-2,4-dione
• CAS: 906546-06-3
• 化学式: C₁₂H₆BrNO₃
• 分子量: 292.089
• InChiKey: SSRYGXOSOGZOCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63.07
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  7-bromo-1H-naphtho-1,3-oxazine-2,4-dione 在 tris(dibenzylideneacetone)dipalladium (0) 三正丁胺 、 P(tol)3 、 sodium carbonate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 乙腈 为溶剂， 反应 52.0h， 生成
  参考文献：
  名称：

  Exploring the Limits of DNA Size:  Naphtho-Homologated DNA Bases and Pairs

  摘要：

  A new design for DNA bases and base pairs is described in which the pyrimidine bases are widened by naphtho-homologation. Two naphtho-homologated deoxyribosides, dyyT (1) and dyyC (2), were synthesized and could be incorporated into oligonucleotides as suitably protected phosphoramidite derivatives. The deoxyribosides were found to be fluorescent, with emission maxima at 446 and 433 nm, respectively. Studies with single substitutions of 1 and 2 in the natural DNA context revealed exceptionally strong base stacking propensity for both. Sequences containing multiple substitutions of 1 and 2 paired opposite adenine and guanine were subsequently mixed and studied by several analytical methods. Data from UV mixing experiments, FRET measurements, fluorescence quenching experiments, and hybridizations on beads suggest that complementary "doublewide DNA" (yyDNA) strands may self-assemble into helical complexes with 1: 1 stoichiometry. Data from thermal denaturation plots and CD spectra were less conclusive. Control experiments in one sequence context gave evidence that yyDNA helices, if formed, are preferentially antiparallel and are sequence selective. Hypothesized base pairing schemes are analogous to Watson-Crick pairing, but with glycosidic C1'-C1' distances widened by over 45%, to ca. 15.2 angstrom. The possible self-assembly of the double-wide DNA helix establishes a new limit for the size of information-encoding, DNA-like molecules, and the fluorescence of yyDNA bases suggests uses as reporters in monomeric and oligomeric forms.

  DOI：

  10.1021/ja0619004
• 作为产物：
  描述：

  3-氨基-2-萘甲酸 在 盐酸 、 tin 、 溴 、 三溴化磷 作用下， 以 四氢呋喃 、 乙醚 、 溶剂黄146 为溶剂， 反应 53.0h， 生成 7-bromo-1H-naphtho-1,3-oxazine-2,4-dione
  参考文献：
  名称：

  Exploring the Limits of DNA Size:  Naphtho-Homologated DNA Bases and Pairs

  摘要：

  A new design for DNA bases and base pairs is described in which the pyrimidine bases are widened by naphtho-homologation. Two naphtho-homologated deoxyribosides, dyyT (1) and dyyC (2), were synthesized and could be incorporated into oligonucleotides as suitably protected phosphoramidite derivatives. The deoxyribosides were found to be fluorescent, with emission maxima at 446 and 433 nm, respectively. Studies with single substitutions of 1 and 2 in the natural DNA context revealed exceptionally strong base stacking propensity for both. Sequences containing multiple substitutions of 1 and 2 paired opposite adenine and guanine were subsequently mixed and studied by several analytical methods. Data from UV mixing experiments, FRET measurements, fluorescence quenching experiments, and hybridizations on beads suggest that complementary "doublewide DNA" (yyDNA) strands may self-assemble into helical complexes with 1: 1 stoichiometry. Data from thermal denaturation plots and CD spectra were less conclusive. Control experiments in one sequence context gave evidence that yyDNA helices, if formed, are preferentially antiparallel and are sequence selective. Hypothesized base pairing schemes are analogous to Watson-Crick pairing, but with glycosidic C1'-C1' distances widened by over 45%, to ca. 15.2 angstrom. The possible self-assembly of the double-wide DNA helix establishes a new limit for the size of information-encoding, DNA-like molecules, and the fluorescence of yyDNA bases suggests uses as reporters in monomeric and oligomeric forms.

  DOI：

  10.1021/ja0619004