[O6-benzyl-8-bromo-guanin-9-yl]acetic acid | 1363676-06-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: [O6-benzyl-8-bromo-guanin-9-yl]acetic acid
• CAS: 1363676-06-5
• 化学式: C₁₄H₁₂BrN₅O₃
• 分子量: 378.185
• InChiKey: HSFNTRGPLYLGGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.83
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  116.15
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  [O6-benzyl-8-bromo-guanin-9-yl]acetic acid 、 tert-butyl N-[2-(N-9-fluorenylmethoxycarbonyl)aminoethyl]glycinate hydrochloride 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以95%的产率得到t-butyl-N-[2-(fluorenylmethoxycarbonyl)aminoethyl]-N-[O6-benzyl-8-bromo-guanin-9-yl]glycine
  参考文献：
  名称：

  8-Vinylguanine Nucleo Amino Acid: A Fluorescent PNA Building Block

  摘要：

  Attachment of a vinyl group at guanine position 8 provides fluorescent properties of the nucleobase. Therefore, 8-vinylguanine was introduced as a 2-aminoethylglycine peptide nucleic acid (PNA) building block. Incorporation of the guanine analog in short PNA sequences by Fmoc solid phase peptide synthesis allowed the differentiation between hybridization states of specific double strands with DNA, RNA, and PNA as well as quadruplex forming RNA/PNA oligomers based on fluorescence intensity.

  DOI：

  10.1021/ol3000603
• 作为产物：
  描述：

  2-(2-amino-6-(benzyloxy)-9H-purin-9-yl)acetic acid 在 溴 作用下， 以 乙酸乙酯 为溶剂， 反应 1.67h， 以61%的产率得到[O6-benzyl-8-bromo-guanin-9-yl]acetic acid
  参考文献：
  名称：

  8-Vinylguanine Nucleo Amino Acid: A Fluorescent PNA Building Block

  摘要：

  Attachment of a vinyl group at guanine position 8 provides fluorescent properties of the nucleobase. Therefore, 8-vinylguanine was introduced as a 2-aminoethylglycine peptide nucleic acid (PNA) building block. Incorporation of the guanine analog in short PNA sequences by Fmoc solid phase peptide synthesis allowed the differentiation between hybridization states of specific double strands with DNA, RNA, and PNA as well as quadruplex forming RNA/PNA oligomers based on fluorescence intensity.

  DOI：

  10.1021/ol3000603