N-iodoacetyl-p-aminoazobenzene | 960124-37-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 英文名称: N-iodoacetyl-p-aminoazobenzene
• 英文别名: N-(4-Phenylazophenyl)iodoacetamide；2-iodo-N-(4-phenyldiazenylphenyl)acetamide
• CAS: 960124-37-2
• 化学式: C₁₄H₁₂IN₃O
• 分子量: 365.173
• InChiKey: GFJMLFLAAWGYAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  53.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  碘乙酸 、 对氮蒽蓝 在 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 以80%的产率得到N-iodoacetyl-p-aminoazobenzene
  参考文献：
  名称：

  Photomodulation of PS-modified oligonucleotides containing azobenzene substituent at pre-selected positions in phosphate backbone

  摘要：

  A new protocol has been developed for incorporation of a photoisomerizable azobenzene moiety into synthetic stereo-enriched [R-p] and [S-p] PS-oligonucleotides. The azobenzene pendant is attached at pre-selected positions in internucleotidic phosphorothioate oligonucleotides of both [R-p] and [S-p] diastereomers using a novel reagent, N-iodoacetyl-p-aminoazobenzene, 1. The modified oligomers are purified on HPLC, characterized by LC-MS, and examined for their thermal and photoisomerization properties. The azobenzene moiety imparts greater stability to oligomer duplexes in (E) N=N con. guration as compared to (Z) configuration. The placement of the azobenzene pendant close to 5'-terminus (n - 1) and 3'-terminus of the modified PS-oligos contributes maximum stability to the duplex while a gradual decline in stability occurs with azobenzene moving toward middle of the duplex. Circular Dichroism studies reveal that the chiral environment at the phosphorus center of the PS-oligos does not alter the global conformation of the DNA duplex as such, suggesting conservation of conformation of the modified DNA strands. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.08.042