5'-Nitro-[2,2']bipyridinyl-5-carboxylic acid methyl ester | 184962-92-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5'-Nitro-[2,2']bipyridinyl-5-carboxylic acid methyl ester
• 英文别名: Methyl 6-(5-nitropyridin-2-yl)pyridine-3-carboxylate
• CAS: 184962-92-3
• 化学式: C₁₂H₉N₃O₄
• 分子量: 259.221
• InChiKey: GBEARIYLCTXGJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  97.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5'-Nitro-[2,2']bipyridinyl-5-carboxylic acid methyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以89%的产率得到5'-Amino-[2,2']bipyridinyl-5-carboxylic acid methyl ester
  参考文献：
  名称：

  New Synthetic Amino Acids for the Design and Synthesis of Peptide-Based Metal Ion Sensors

  摘要：

  The syntheses of two new nonstandard amino acids, Flu (6) and YBp (20), and a new synthesis of Dmd (12) are reported. These residues exhibit fluorescence, metal-coordination, and fluorescence-quenching properties, respectively. These building blocks have been incorporated into peptides via solid phase peptide synthesis to afford the prototype fur a photoinduced electron transfer-based metal ion chemosensor. The fluorescence of the peptides is modulated upon metal binding. This results from a metal. ion-induced conformational change that brings the side chains of the Flu and Dmd amino acids into proximity, thereby favoring photoinduced electron transfer (PET) fluorescence quenching.

  DOI：

  10.1021/jo961466w
• 作为产物：
  描述：

  6-羟基烟酸甲酯 在 四(三苯基膦)钯 、 三乙胺 、 lithium chloride 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 60.0h， 生成 5'-Nitro-[2,2']bipyridinyl-5-carboxylic acid methyl ester
  参考文献：
  名称：

  New Synthetic Amino Acids for the Design and Synthesis of Peptide-Based Metal Ion Sensors

  摘要：

  The syntheses of two new nonstandard amino acids, Flu (6) and YBp (20), and a new synthesis of Dmd (12) are reported. These residues exhibit fluorescence, metal-coordination, and fluorescence-quenching properties, respectively. These building blocks have been incorporated into peptides via solid phase peptide synthesis to afford the prototype fur a photoinduced electron transfer-based metal ion chemosensor. The fluorescence of the peptides is modulated upon metal binding. This results from a metal. ion-induced conformational change that brings the side chains of the Flu and Dmd amino acids into proximity, thereby favoring photoinduced electron transfer (PET) fluorescence quenching.

  DOI：

  10.1021/jo961466w

文献信息

• New Synthetic Amino Acids for the Design and Synthesis of Peptide-Based Metal Ion Sensors
  作者：Alicia Torrado、Barbara Imperiali

  DOI：10.1021/jo961466w

  日期：1996.1.1

  The syntheses of two new nonstandard amino acids, Flu (6) and YBp (20), and a new synthesis of Dmd (12) are reported. These residues exhibit fluorescence, metal-coordination, and fluorescence-quenching properties, respectively. These building blocks have been incorporated into peptides via solid phase peptide synthesis to afford the prototype fur a photoinduced electron transfer-based metal ion chemosensor. The fluorescence of the peptides is modulated upon metal binding. This results from a metal. ion-induced conformational change that brings the side chains of the Flu and Dmd amino acids into proximity, thereby favoring photoinduced electron transfer (PET) fluorescence quenching.