N-benzoyl-3-(5-aminopyridin-2-yl)-6-(pyridin-2-yl)-s-tetrazine | 1055983-03-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-benzoyl-3-(5-aminopyridin-2-yl)-6-(pyridin-2-yl)-s-tetrazine
• 英文别名: N-benzoyl-3-(5-aminopyridin-2-yl)-6-(pyridin-2-yl)-1,2,4,5-tetrazine；N-[6-(6-pyridin-2-yl-1,2,4,5-tetrazin-3-yl)pyridin-3-yl]benzamide
• CAS: 1055983-03-3
• 化学式: C₁₉H₁₃N₇O
• 分子量: 355.359
• InChiKey: SEGUVTKDSZSDAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  6-(6-(吡啶-2-基)-1,2,4,5-四嗪-3-基)吡啶-3-胺 、 苯甲酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 12.0h， 以61%的产率得到N-benzoyl-3-(5-aminopyridin-2-yl)-6-(pyridin-2-yl)-s-tetrazine
  参考文献：
  名称：

  Tetrazine Ligation: Fast Bioconjugation Based on Inverse-Electron-Demand Diels−Alder Reactivity

  摘要：

  Described is a bioorthogonal reaction that proceeds with unusually fast reaction rates without need for catalysis: the cycloaddition of s-tetrazine and trans-cyclooctene derivatives. The reactions tolerate a broad range of functionality and proceed in high yield in organic solvents, water, cell media, or cell lysate. The rate of the ligation between trans-cyclooctene and 3,6-di-(2-pyridyl)-s-tetrazine is very rapid (k(2) 2000 M-1 s(-1)). This fast reactivity enables protein modification at low concentration.

  DOI：

  10.1021/ja8053805

文献信息

• TETRAZINE-BASED BIO-ORTHOGONAL COUPLING REAGENTS AND METHODS
  申请人：Fox Joseph Michael

  公开号：US20090023916A1

  公开（公告）日：2009-01-22

  Coupling reactions, suitable for use in organic or aqueous media, are performed by contacting a 1,2,4,5-tetrazine with a dienophile. The dienophile may be covalently bonded to a protein, and the coupling reaction may be performed in biological media such as those containing cells or cell lysates. The reactions may be performed in the presence of primary amines, thiols, acetylenes, azides, phosphines, and products of Staudinger and/or Sharpless-Huisgen reactions Novel 3-substituted cyclopropene compounds and trans-cyclooctenes are exemplary dienophiles for these reactions.

  耦合反应，适用于有机或水性介质，通过将1,2,4,5-四唑与二烯丙烯发生反应来进行。二烯丙烯可能与蛋白质共价结合，耦合反应可在含有细胞或细胞裂解产物的生物介质中进行。这些反应可在存在主要胺基、硫醇、乙炔、叠氮化物、膦化合物以及Staudinger和/或Sharpless-Huisgen反应产物的情况下进行。新颖的3-取代环丙烯化合物和反式-环辛烯是这些反应的优秀二烯丙烯。
• US8236949B2
  申请人：——

  公开号：US8236949B2

  公开（公告）日：2012-08-07
• Tetrazine Ligation: Fast Bioconjugation Based on Inverse-Electron-Demand Diels−Alder Reactivity
  作者：Melissa L. Blackman、Maksim Royzen、Joseph M. Fox

  DOI：10.1021/ja8053805

  日期：2008.10.15

  Described is a bioorthogonal reaction that proceeds with unusually fast reaction rates without need for catalysis: the cycloaddition of s-tetrazine and trans-cyclooctene derivatives. The reactions tolerate a broad range of functionality and proceed in high yield in organic solvents, water, cell media, or cell lysate. The rate of the ligation between trans-cyclooctene and 3,6-di-(2-pyridyl)-s-tetrazine is very rapid (k(2) 2000 M-1 s(-1)). This fast reactivity enables protein modification at low concentration.