1-(2,4-dinitrophenyl)-imidazole 4-acetic acid | 153527-31-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(2,4-dinitrophenyl)-imidazole 4-acetic acid
• 英文别名: [1-(2,4-dinitrophenyl)-1H-imidazol-4-yl]acetic acid；2-[1-(2,4-Dinitrophenyl)imidazol-4-yl]acetic acid
• CAS: 153527-31-2
• 化学式: C₁₁H₈N₄O₆
• 分子量: 292.208
• InChiKey: BMJOJCZWDPVFQY-UHFFFAOYSA-N

物化性质

• 沸点：
  571.5±50.0 °C(predicted)
• 密度：
  1.68±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  147
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(2,4-dinitrophenyl)-imidazole 4-acetic acid 在 N-甲基咪唑 、 2,4,6-三异丙基苯磺酰氯 、 五氟苯酚 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 反应 52.42h， 生成 [2'-deoxythymidylyl(5'-3')-2'-deoxythymidin-5'-yl] {4-[N^α-(1H-imidazol-4-ylacetyl)-L-histidyl]aminobutyl} phosphate lithium salt
  参考文献：
  名称：

  Reagents for addressed modification of biopolymers

  摘要：

  Derivatives of histidine, imidazolylacetic and urocanic acids, containing an N-lm-2,4-dinitrophenyl moiety and a hydroxy group were synthesized and characterized. The applicability of these reagents for anchoring imidazole residues to oligonucleotides to give potential site-specific artificial ribonucleases was shown taking the synthesis of dinucleotide derivatives as an example.

  DOI：

  10.1007/bf02494790
• 作为产物：
  描述：

  4-咪唑乙酸盐酸盐 、 2,4-二硝基氟苯 在 sodium hydroxide 、 碳酸氢钠 作用下， 以 甲醇 、 水 为溶剂， 反应 4.0h， 以72%的产率得到1-(2,4-dinitrophenyl)-imidazole 4-acetic acid
  参考文献：
  名称：

  Reagents for addressed modification of biopolymers

  摘要：

  Derivatives of histidine, imidazolylacetic and urocanic acids, containing an N-lm-2,4-dinitrophenyl moiety and a hydroxy group were synthesized and characterized. The applicability of these reagents for anchoring imidazole residues to oligonucleotides to give potential site-specific artificial ribonucleases was shown taking the synthesis of dinucleotide derivatives as an example.

  DOI：

  10.1007/bf02494790

文献信息

• Expansion of repertoire of modified DNAs prepared by PCR using KOD Dash DNA polymerase
  作者：Tsutomu Ohbayashi、Masayasu Kuwahara、Masatoshi Hasegawa、Toshiyuki Kasamatsu、Takehiro Tamura、Hiroaki Sawai

  DOI：10.1039/b504330a

  日期：——

  Thymidine analogues bearing a variety of functional groups at the C5-position via an amino-linker arm were prepared and the substrate activity for PCR using thermophilic KOD Dash DNA polymerase was examined. The enzyme accepted the thymidine analogues bearing pyridine, imidazole, biotin, a cationic-charged guanidinium, a cationic-charged amino, mercaptopyridyl and phenanthrolne groups at the C5-position

  制备了通过氨基连接臂在C5位带有各种官能团的胸苷类似物，并检测了使用嗜热KOD Dash DNA聚合酶进行PCR的底物活性。该酶接受在C5位带有吡啶，咪唑，生物素，阳离子带电的胍盐，阳离子带电的氨基，巯基吡啶基和菲咯啉基团的胸苷类似物，形成相应的PCR产物。然而，在C5位带有羧基的胸苷类似物是较差的底物，无法获得相应的PCR产物。带有巯基的胸苷类似物也是该酶的不良底物，因为它在PCR条件下通过二硫键二聚。该酶几乎不接受带有负电荷的羧基或大体积基团的胸苷类似物作为底物。KOD Dash DNA聚合酶具有比其他任何DNA聚合酶都要宽的底物特异性，它将扩展可通过PCR制备的修饰DNA的种类。
• Synthesis of oligonucleotides containing N2-[2-(imidazol-4-ylacetamido)ethyll-2′-deoxyguanosine
  作者：Guangyi Wang、Donald E. Bergstrom

  DOI：10.1016/s0040-4039(00)61685-4

  日期：1993.10

  Synthesis of 2′-deoxyguanosine tethered through N-2 to an imidazole is described. The modified 2′-deoxyguanosine was converted to two different phosphoramidites, one with and the other without a 6-O-protecting group. The phosphoramidites were incorporated into oligonucleotide alone or together with a 2′-deoxyuridine tethered to a bipyridine. Protection and deprotection of the imidazole are also briefly

  描述了通过N-2连接到咪唑的2'-脱氧鸟苷的合成。修饰的2'-脱氧鸟苷被转化为两种不同的亚磷酰胺，一种具有6- O-保护基，另一种具有6- O-保护基。将亚磷酰胺单独或与束缚到联吡啶的2'-脱氧尿苷一起掺入寡核苷酸中。还简要描述了咪唑的保护和脱保护。