5,5'-bis[(2,2'-dipicolylamino)methyl]-2,2'-bipyridine

• 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: 5,5'-bis[(2,2'-dipicolylamino)methyl]-2,2'-bipyridine
• 英文别名: 1-[6-[5-[[bis(2-pyridylmethyl)amino]methyl]-2-pyridyl]-3-pyridyl]-N,N-bis(2-pyridylmethyl)methanamine；1-[6-[5-[[bis(pyridin-2-ylmethyl)amino]methyl]pyridin-2-yl]pyridin-3-yl]-N,N-bis(pyridin-2-ylmethyl)methanamine
• 化学式: C₃₆H₃₄N₈
• 分子量: 578.72
• InChiKey: DDEMCLFTJUWMGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  44
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  83.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  zinc(II) acetate dihydrate 、 5,5'-bis[(2,2'-dipicolylamino)methyl]-2,2'-bipyridine 以 甲醇 为溶剂， 以61%的产率得到
  参考文献：
  名称：

  Evaluation of Multisite Polypyridyl Ligands as Platforms for the Synthesis of Rh/Zn, Rh/Pd, and Rh/Pt Heterometallic Complexes

  摘要：

  Ligands containing linked dipicolylamine (dpa) and bipyridine (bpy) sites have been utilized in the synthesis of monometallic and heterometallic complexes. The two sites have different selectivities for metal binding, which allows preferential formation of singly metalated complexes. The dpa site of the ligands has been observed to bind selectively to Zn2+, Pd2+, and Pt2+, while the bpy site binds selectively to Rh+. Addition of a second metal then results in the formation of heterometallic products. In the presence of CD3OD, the heterometallic Rh/Pt and Rh/Pd complexes undergo rapid selective H/D exchange of one of the diastereotopic protons of the dpa methylene group.

  DOI：

  10.1021/ic301810y
• 作为产物：
  描述：

  5 5'-二甲基-2,2'-二吡啶 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 potassium carbonate 作用下， 以 四氢呋喃 、 四氯化碳 为溶剂， 反应 41.0h， 生成 5,5'-bis[(2,2'-dipicolylamino)methyl]-2,2'-bipyridine
  参考文献：
  名称：

  Evaluation of Multisite Polypyridyl Ligands as Platforms for the Synthesis of Rh/Zn, Rh/Pd, and Rh/Pt Heterometallic Complexes

  摘要：

  Ligands containing linked dipicolylamine (dpa) and bipyridine (bpy) sites have been utilized in the synthesis of monometallic and heterometallic complexes. The two sites have different selectivities for metal binding, which allows preferential formation of singly metalated complexes. The dpa site of the ligands has been observed to bind selectively to Zn2+, Pd2+, and Pt2+, while the bpy site binds selectively to Rh+. Addition of a second metal then results in the formation of heterometallic products. In the presence of CD3OD, the heterometallic Rh/Pt and Rh/Pd complexes undergo rapid selective H/D exchange of one of the diastereotopic protons of the dpa methylene group.

  DOI：

  10.1021/ic301810y

文献信息

• Cross-Linking Strategy for Molecular Recognition and Fluorescent Sensing of a Multi-phosphorylated Peptide in Aqueous Solution
  作者：Akio Ojida、Masa-aki Inoue、Yasuko Mito-oka、Itaru Hamachi

  DOI：10.1021/ja036317r

  日期：2003.8.1

  the research field of molecular recognition, selective recognition and sensing of phosphorylated protein surfaces is strongly desirable both for elucidation of protein-protein recognition at the molecular level and for regulation of signal transduction through protein surfaces. Here we describe a new strategy for molecular recognition of a multi-phosphorylated peptide using intrapeptide cross-linking

  在分子识别研究领域，磷酸化蛋白质表面的选择性识别和感知对于阐明分子水平的蛋白质-蛋白质识别和通过蛋白质表面的信号转导的调节是非常需要的。在这里，我们描述了一种基于配位化学使用肽内交联来分子识别多磷酸化肽的新策略。本人工受体可通过多点相互作用选择性结合双磷酸化肽，并在中性水溶液中以大于106 M-1的结合常数对结合事件进行荧光感应。
• Heterobimetallic Complexes of Polypyridyl Ligands Containing Paramagnetic Centers: Synthesis and Characterization by IR and EPR
  作者：Sarah K. Goforth、Richard C. Walroth、Joseph A. Brannaka、Alexander Angerhofer、Lisa McElwee-White

  DOI：10.1021/ic401952s

  日期：2013.12.16

  Ligands containing linked dipicolylamine (dpa) and bipyridine sites have been explored as platforms for the synthesis of heterometallic complexes containing the paramagnetic metals Cu2+ and Co2+. IR and EPR studies on the bimetallic complexes and simplified model compounds support dpa-selective binding by both of these metals. The IR spectra have also been compared to those of diamagnetic Rh+, Zn2+

  已经研究了包含连接的二聚烯丙基胺（dpa）和联吡啶位点的配体作为合成包含顺磁性金属Cu 2+和Co 2+的杂金属配合物的平台。对双金属配合物和简化模型化合物的IR和EPR研究支持这两种金属对dpa的选择性结合。还已将IR光谱与抗磁性Rh +，Zn 2+和Pd 2+络合物的光谱进行了比较，它们的金属结合位点已通过NMR技术独立确定。结合偏好已用于控制异金属Pt / Cu，Pd / Cu和Rh / Cu络合物合成中的选择性金属化。
• Effective Disruption of Phosphoprotein−Protein Surface Interaction Using Zn(II) Dipicolylamine-Based Artificial Receptors via Two-Point Interaction
  作者：Akio Ojida、Masa-aki Inoue、Yasuko Mito-oka、Hiroshi Tsutsumi、Kazuki Sada、Itaru Hamachi

  DOI：10.1021/ja056585k

  日期：2006.2.1

  Protein phosphorylation is ubiquitously involved in living cells, and it is one of the key events controlling protein-protein surface interactions, which are essential in signal transduction cascades. We now report that the small molecular receptors bearing binuclear Zn(ll)-Dpa can strongly bind to a bisphosphorylated peptide in a cross-linking manner under neutral aqueous conditions when the distance between the two Zn(ll) centers can appropriately fit in that of the two phosphate groups of the phosphorylated peptide. The binding property was quantitatively determined by ITC (isothermal titration calorimetry), induced CD (circular dichroism), and NMR. On the basis of these findings, we demonstrated that these types of small molecules were able to effectively disrupt the phosphoprotein-protein interaction in a phosphorylated CTD peptide and the Pin1 WW domain, a phosphoprotein binding domain, at a micromolar level. The strategy based on a small molecular disruptor that directly interacts with phosphoprotein is unique and should be promising in developing a designer inhibitor for phosphoprotein-protein interaction.