N2-tert-butoxycarbonyl-5-methylisocytosine | 1292200-55-5

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: N2-tert-butoxycarbonyl-5-methylisocytosine
• 英文别名: tert-butyl N-(4-hydroxy-5-methylpyrimidin-2-yl)carbamate；tert-butyl N-(5-methyl-6-oxo-1H-pyrimidin-2-yl)carbamate
• CAS: 1292200-55-5
• 化学式: C₁₀H₁₅N₃O₃
• 分子量: 225.247
• InChiKey: PFWNRLZTAYOKII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  79.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N2-tert-butoxycarbonyl-5-methylisocytosine 在 potassium carbonate 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.33h， 生成 benzyl 2-((2-(((9H-fluoren-9-yl)methoxy)carbonylamino)ethyl)(tert-butoxycarbonyl)amino)acetate
  参考文献：
  名称：

  PNA containing isocytidine nucleobase: Synthesis and recognition of double helical RNA

  摘要：

  Peptide nucleic acid (PNA1) containing a 5-methylisocytidine (iC) nucleobase has been synthesized. Triple helix formation between PNA1 and RNA hairpins having variable base pairs interacting with iC was studied using isothermal titration calorimetry. The iC nucleobase recognized the proposed target, C-G inversion in polypurine tract of RNA, with slightly higher affinity than the natural nucleobases, though the sequence selectivity of recognition was low. Compared to non-modified PNA, PNA1 had lower affinity for its RNA target. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.130
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 2-氨基-5-甲基-4-嘧啶醇 在 4-二甲氨基吡啶 作用下， 以 吡啶 为溶剂， 反应 16.0h， 以54%的产率得到N2-tert-butoxycarbonyl-5-methylisocytosine
  参考文献：
  名称：

  PNA containing isocytidine nucleobase: Synthesis and recognition of double helical RNA

  摘要：

  Peptide nucleic acid (PNA1) containing a 5-methylisocytidine (iC) nucleobase has been synthesized. Triple helix formation between PNA1 and RNA hairpins having variable base pairs interacting with iC was studied using isothermal titration calorimetry. The iC nucleobase recognized the proposed target, C-G inversion in polypurine tract of RNA, with slightly higher affinity than the natural nucleobases, though the sequence selectivity of recognition was low. Compared to non-modified PNA, PNA1 had lower affinity for its RNA target. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.130

文献信息

• PNA containing isocytidine nucleobase: Synthesis and recognition of double helical RNA
  作者：Thomas Zengeya、Ming Li、Eriks Rozners

  DOI：10.1016/j.bmcl.2011.01.130

  日期：2011.4

  Peptide nucleic acid (PNA1) containing a 5-methylisocytidine (iC) nucleobase has been synthesized. Triple helix formation between PNA1 and RNA hairpins having variable base pairs interacting with iC was studied using isothermal titration calorimetry. The iC nucleobase recognized the proposed target, C-G inversion in polypurine tract of RNA, with slightly higher affinity than the natural nucleobases, though the sequence selectivity of recognition was low. Compared to non-modified PNA, PNA1 had lower affinity for its RNA target. (C) 2011 Elsevier Ltd. All rights reserved.