<2,2'-bipyridine>-5,5'-dicarboxylic acid bis(N-hydroxysuccinimide) ester | 219134-87-9

• 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: <2,2'-bipyridine>-5,5'-dicarboxylic acid bis(N-hydroxysuccinimide) ester
• 英文别名: (2,2'-bipyridine)-5,5'-dicarboxylic acid bis(N-hydroxysuccinimide) ester；bis(succinimidyl) 2,2′-bipyridine-5,5′-dicarboxylate；(2,5-Dioxopyrrolidin-1-yl) 6-[5-(2,5-dioxopyrrolidin-1-yl)oxycarbonylpyridin-2-yl]pyridine-3-carboxylate；(2,5-dioxopyrrolidin-1-yl) 6-[5-(2,5-dioxopyrrolidin-1-yl)oxycarbonylpyridin-2-yl]pyridine-3-carboxylate
• CAS: 219134-87-9
• 化学式: C₂₀H₁₄N₄O₈
• 分子量: 438.353
• InChiKey: MPKBIXXXLNZREG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  153
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  <2,2'-bipyridine>-5,5'-dicarboxylic acid bis(N-hydroxysuccinimide) ester 在 三乙基硅烷 、 三乙胺 、 三氟乙酸 、 sodium hydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 187.0h， 生成 (8R,13R,23R,28R)-6,15,21,30-tetraoxo-10,11,25,26-tetrathia-3,7,14,18,22,29,33-heptazatetracyclo[29.2.2.22,5.116,20]octatriaconta-1(33),2,4,16(36),17,19,31,34,37-nonaene-8,13,23,28-tetracarboxylic acid
  参考文献：
  名称：

  Dynamic Combinatorial Chemistry with Novel Dithiol Building Blocks: Towards New Structurally Diverse and Adaptive Screening Collections

  摘要：

  We describe the synthesis of a range of novel dithiol-functionalized building blocks and demonstrate how they can be used to generate new structurally diverse dynamic combinatorial libraries. A proof-of-principle experiment using the catecholamine dopamine revealed that molecular recognition changed the library composition under biocompatible conditions and identified new promising candidate receptors of this biologically important neurotransmitter.

  DOI：

  10.1055/s-0032-1318407
• 作为产物：
  描述：

  5 5'-二甲基-2,2'-二吡啶 在 吡啶 、 硫酸 、 氯苯 、 三氟乙酸酐 作用下， 以 1,4-二氧六环 、 乙酸乙酯 为溶剂， 反应 38.25h， 生成 <2,2'-bipyridine>-5,5'-dicarboxylic acid bis(N-hydroxysuccinimide) ester
  参考文献：
  名称：

  Dynamic Combinatorial Chemistry with Novel Dithiol Building Blocks: Towards New Structurally Diverse and Adaptive Screening Collections

  摘要：

  We describe the synthesis of a range of novel dithiol-functionalized building blocks and demonstrate how they can be used to generate new structurally diverse dynamic combinatorial libraries. A proof-of-principle experiment using the catecholamine dopamine revealed that molecular recognition changed the library composition under biocompatible conditions and identified new promising candidate receptors of this biologically important neurotransmitter.

  DOI：

  10.1055/s-0032-1318407

文献信息

• Synthesis and Self-Inclusion of Bipyridine-Spaced Cyclodextrin Dimers
  作者：Hubertus F. M. Nelissen、Martinus C. Feiters、Roeland J. M. Nolte

  DOI：10.1021/jo0256641

  日期：2002.8.1

  The synthesis and conformational behavior of two cyclodextrin dimers containing aromatic bipyridine spacers is presented. The proton NMR spectra of these dimers in aqueous solution show a doubling of signals in the aromatic region due to complete or partial self-inclusion of the spacer. The degree and the strength of self-inclusion is dependent on the substitution pattern of the bipyridine unit. This

  提出了两个含有芳香联吡啶间隔基的环糊精二聚体的合成和构象行为。这些二聚体在水溶液中的质子NMR光谱显示，由于间隔基的完全或部分自包含，芳香族区域的信号加倍。自我包容的程度和强度取决于联吡啶单元的取代方式。2D NOESY和圆二色性光谱揭示了这种自包含行为的出乎意料的差异。
• Synthesis and binding properties of novel cyclodextrin dimers
  作者：Fokke Venema、Chantal M. Baselier、Erik van Dienst、Bianca H.M. Ruël、Martinus C. Feiters、Johan F.J. Engbersen、David N. Reinhoudt、Roeland J.M. Nolte

  DOI：10.1016/0040-4039(94)88343-2

  日期：1994.3

  The synthesis of three cyclodextrin dimers from the novel building block 3-amino-3-deoxy-heptakis(6-O-tert-butyldimethylsilyl)-β-cyclodextrin is reported. The cyclodextrins are linked with an amide bond on their secondary sides to an ethylene, octamethylene, or a metal binding bipyridyl group. Complexation studies with the substrate 6-(p-toluidino)-2-naphthalenesulfonic acid are presented and discussed

  据报道，由新型结构单元3-氨基-3-脱氧庚七（6-O-叔丁基二甲基甲硅烷基）-β-环糊精合成了三个环糊精二聚体。环糊精在其次级侧通过酰胺键与亚乙基，八亚甲基或与金属结合的联吡啶基连接。提出并讨论了与底物6-（对甲苯基）-2-萘磺酸的络合研究。
• Synthesis, Conformation, and Binding Properties of Cyclodextrin Homo- and Heterodimers Connected through Their Secondary Sides
  作者：Fokke Venema、Hubertus F. M. Nelissen、Patrick Berthault、Nicolaos Birlirakis、Alan E. Rowan、Martinus C. Feiters、Roeland J. M. Nolte

  DOI：10.1002/(sici)1521-3765(19981102)4:11<2237::aid-chem2237>3.0.co;2-4

  日期：1998.11.2

  The synthesis of homo- and heterocyclodextrin (CD) dimers, containing two CD moieties that are linked through their secondary sides by aliphatic or 2,2'-bipyridyl spacers is described. In these dimers, the glucose units to which the spacers are linked have been transformed into altrose units. The dimers with an octamethylene spacer show self-complexation of the spacer in one of the CD moieties in aqueous solution, as revealed by H-1 and C-13 NMR spectroscopy. Using high-resolution (600 and 800 MHz) NMR spectroscopy and a variety of 2D NMR techniques, an assignment of nearly all of the H-1 NMR signals of two of the CD dimers was made, affording detailed information about the structure of these compounds in water. The self-inclusion of the spacers leads to lower binding affinities for ditopic guest molecules like p-toluidino-6-naphthalene sulfonate (TNS) derivatives and porphyrins. When a rigid 2,2'-bipyridyl group is used to connect the two CD moieties, self-inclusion of the spacer is not possible. This results in the formation of different complexes with ditopic guest molecules, for example, a 2:2 complex with a porphyrin.The CD heterodimers described in this paper contain an alpha-CD and a beta-CD moiety. These dimers display site-specific binding of guest molecules.