6-(2-(pyridin-2-yl)pyrimidine-4-carboxamido)hexanoic acid | 1363691-64-8

• 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: 6-(2-(pyridin-2-yl)pyrimidine-4-carboxamido)hexanoic acid
• 英文别名: 6-[(2-Pyridin-2-ylpyrimidine-4-carbonyl)amino]hexanoic acid；6-[(2-pyridin-2-ylpyrimidine-4-carbonyl)amino]hexanoic acid
• CAS: 1363691-64-8
• 化学式: C₁₆H₁₈N₄O₃
• 分子量: 314.344
• InChiKey: QSIMMYQBOFJKIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-(2-(pyridin-2-yl)pyrimidine-4-carboxamido)hexanoic acid 、 tert-butyl N-(2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}ethyl)glycinate 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以82%的产率得到tert-butyl-N-[2-(N-9-fluorenylmethoxycarbonyl)aminoethyl]-N-[6-(2-(pyridin-2-yl) pyrimidine-4-carboxamido)hexanoyl]glycinate
  参考文献：
  名称：

  Electrochemiluminescent Monomers for Solid Support Syntheses of Ru(II)-PNA Bioconjugates: Multimodal Biosensing Tools with Enhanced Duplex Stability

  摘要：

  The feasibility of devising a solid support mediated approach to multimodal Ru(II)-peptide nucleic acid (PNA) oligomers is explored. Three Ru(II)-PNA-like monomers, [Ru(bpy)(2)(Cpp-L-PNA-OH)](2+) (M1), [Ru(phen)(2)(Cpp-L-PNA-OH)](2+) (M2), and [Ru(dppz)(2)(Cpp-L-PNA-OH)](2+) (M3) (bpy = 2,2'-bipyridine, phen = 1,10-phenanthroline, dppz = dipyrido[3,2-a:2',3'-c]phenazine, Cpp-L-PNA-OH = [2-(N-9-fluorenylmethoxycarbonyl)aminoethyl]-N-[6-(2-(pyridin-2yl)pyrimidine-4-carboxamido)hexanoyl]-glycine), have been synthesized as building blocks for Ru(II)-PNA oligomers and characterized by IR and H-1 NMR spectroscopy, mass spectrometry, electrochemistry and elemental analysis. As a proof of principle, M1 was incorporated on the solid phase within the PNA sequences H-g-c-a-a-t-a-a-a-a-Lys-NH2 (PNA1) and H-P-K-K-K-R-K-V-g-c-a-a-t-a-a-a-a-lys-NH2 (PNA4) to give PNA2(H-g-c-a-a-t-a-a-a-a-M1-lys-NH2) and PNA3 (H-P-K-K-K-R-K-V-g-c-a-a-t-a-a-a-a-M1-lys-NH2), respectively. The two Ru(II) PNA oligomers, PNA2 and PNA3, displayed a metal to ligand charge transfer (MLCT) transition band centered around 445 nm and an emission maximum at about 680 nm following 450 nm excitation in aqueous solutions (10 mM PBS, pH 7.4). The absorption and emission response, of the duplexes formed with the cDNA strand (DNA: 5'-T-T-T-T-T-T-T-A-T-T-G-C-T-T-T-3') showed no major Variations, suggesting that the electronic properties of the Ru(II) complexes are largely unaffected by hybridization. The thermal stability of the PNA center dot DNA duplexes, as evaluated from UV melting experiments, is enhanced compared to the corresponding nonmetalated duplexes. The melting temperature (T-m) was almost 8 degrees C higher for PNA2 center dot DNA duplex, and 4 degrees C for PNA3 center dot DNA duplex, with the stabilization attributed to the electrostatic interaction between the cationic residues (Ru(II) unit and positively charged lysine/arginine) and the polyanionic DNA backbone. In presence of tripropylamine (TPA) as co-reactant, PNA2, PNA3, PNA2 center dot DNA and PNA3 center dot DNA displayed strong electrochemiluminescence (ECL) signals even at submicromolar concentrations. Importantly, the combination of spectrochemical, thermal and ECL properties possessed by the Ru(II)-PNA sequences offer an elegant approach for the design of highly sensitive multimodal biosensing tools.

  DOI：

  10.1021/ic202761w
• 作为产物：
  描述：

  6-氨基-己酸乙酯盐酸盐 在 4-二甲氨基吡啶 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 sodium hydroxide 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 32.0h， 生成 6-(2-(pyridin-2-yl)pyrimidine-4-carboxamido)hexanoic acid
  参考文献：
  名称：

  Electrochemiluminescent Monomers for Solid Support Syntheses of Ru(II)-PNA Bioconjugates: Multimodal Biosensing Tools with Enhanced Duplex Stability

  摘要：

  The feasibility of devising a solid support mediated approach to multimodal Ru(II)-peptide nucleic acid (PNA) oligomers is explored. Three Ru(II)-PNA-like monomers, [Ru(bpy)(2)(Cpp-L-PNA-OH)](2+) (M1), [Ru(phen)(2)(Cpp-L-PNA-OH)](2+) (M2), and [Ru(dppz)(2)(Cpp-L-PNA-OH)](2+) (M3) (bpy = 2,2'-bipyridine, phen = 1,10-phenanthroline, dppz = dipyrido[3,2-a:2',3'-c]phenazine, Cpp-L-PNA-OH = [2-(N-9-fluorenylmethoxycarbonyl)aminoethyl]-N-[6-(2-(pyridin-2yl)pyrimidine-4-carboxamido)hexanoyl]-glycine), have been synthesized as building blocks for Ru(II)-PNA oligomers and characterized by IR and H-1 NMR spectroscopy, mass spectrometry, electrochemistry and elemental analysis. As a proof of principle, M1 was incorporated on the solid phase within the PNA sequences H-g-c-a-a-t-a-a-a-a-Lys-NH2 (PNA1) and H-P-K-K-K-R-K-V-g-c-a-a-t-a-a-a-a-lys-NH2 (PNA4) to give PNA2(H-g-c-a-a-t-a-a-a-a-M1-lys-NH2) and PNA3 (H-P-K-K-K-R-K-V-g-c-a-a-t-a-a-a-a-M1-lys-NH2), respectively. The two Ru(II) PNA oligomers, PNA2 and PNA3, displayed a metal to ligand charge transfer (MLCT) transition band centered around 445 nm and an emission maximum at about 680 nm following 450 nm excitation in aqueous solutions (10 mM PBS, pH 7.4). The absorption and emission response, of the duplexes formed with the cDNA strand (DNA: 5'-T-T-T-T-T-T-T-A-T-T-G-C-T-T-T-3') showed no major Variations, suggesting that the electronic properties of the Ru(II) complexes are largely unaffected by hybridization. The thermal stability of the PNA center dot DNA duplexes, as evaluated from UV melting experiments, is enhanced compared to the corresponding nonmetalated duplexes. The melting temperature (T-m) was almost 8 degrees C higher for PNA2 center dot DNA duplex, and 4 degrees C for PNA3 center dot DNA duplex, with the stabilization attributed to the electrostatic interaction between the cationic residues (Ru(II) unit and positively charged lysine/arginine) and the polyanionic DNA backbone. In presence of tripropylamine (TPA) as co-reactant, PNA2, PNA3, PNA2 center dot DNA and PNA3 center dot DNA displayed strong electrochemiluminescence (ECL) signals even at submicromolar concentrations. Importantly, the combination of spectrochemical, thermal and ECL properties possessed by the Ru(II)-PNA sequences offer an elegant approach for the design of highly sensitive multimodal biosensing tools.

  DOI：

  10.1021/ic202761w

文献信息

• Synthesis, Spectroscopic Properties, and Photoinduced CO-Release Studies of Functionalized Ruthenium(II) Polypyridyl Complexes: Versatile Building Blocks for Development of CORM–Peptide Nucleic Acid Bioconjugates
  作者：Caroline Bischof、Tanmaya Joshi、Aakanksha Dimri、Leone Spiccia、Ulrich Schatzschneider

  DOI：10.1021/ic400746n

  日期：2013.8.19

  series of ruthenium(II) dicarbonyl complexes of formula [RuCl2(L)(CO)2] (L = bpyCH3,CH3 = 4,4′-dimethyl-2,2′-bipyridine, bpyCH3,CHO = 4′-methyl-2,2′-bipyridine-4-carboxyaldehyde, bpyCH3,COOH = 4′-methyl-2,2′-bipyridine-4-carboxylic acid, CppH = 2-(pyridin-2-yl)pyrimidine-4-carboxylic acid, dppzcH = dipyrido[3,2-a:2′,3′-c]phenazine-11-carboxylic acid), and [RuCl(L)(CO)2]+ (L = tpyCOOH = 6-(2,2′:6′,2″-ter

  一系列式[RuCl 2（L）（CO）2 ]的钌（II）二羰基配合物（L = bpy CH3，CH3 = 4,4'-二甲基-2,2'-联吡啶，bpy CH3，CHO = 4 '-甲基-2,2'-联吡啶-4-羧醛，bpy CH3，COOH = 4'-甲基-2,2'-联吡啶-4-羧酸，CppH = 2-（吡啶-2-基）嘧啶- 4-羧酸，dppzcH =二吡啶基[3,2-a：2'，3'-c]吩嗪-11-羧酸）和[RuCl（L）（CO）2 ] +（L = tpy COOH合成了6-（2,2'：6'，2''-叔吡啶-4'-酰氧基）己酸）。此外，还开发了高产率的含有2-（吡啶-2-基）嘧啶配体的肽核酸（PNA）单体的合成方法，并将该化合物用于制备第一个Ru（II）二羰基配合物，将[RuCl 2（CPP-L-PNA）（CO）2 ]，（CPP-L-PNA =叔丁基- ñ - [2-（ñ -9-芴）氨基乙基]
• Electrochemiluminescent Monomers for Solid Support Syntheses of Ru(II)-PNA Bioconjugates: Multimodal Biosensing Tools with Enhanced Duplex Stability
  作者：Tanmaya Joshi、Gregory J. Barbante、Paul S. Francis、Conor F. Hogan、Alan M. Bond、Gilles Gasser、Leone Spiccia

  DOI：10.1021/ic202761w

  日期：2012.3.5

  The feasibility of devising a solid support mediated approach to multimodal Ru(II)-peptide nucleic acid (PNA) oligomers is explored. Three Ru(II)-PNA-like monomers, [Ru(bpy)(2)(Cpp-L-PNA-OH)](2+) (M1), [Ru(phen)(2)(Cpp-L-PNA-OH)](2+) (M2), and [Ru(dppz)(2)(Cpp-L-PNA-OH)](2+) (M3) (bpy = 2,2'-bipyridine, phen = 1,10-phenanthroline, dppz = dipyrido[3,2-a:2',3'-c]phenazine, Cpp-L-PNA-OH = [2-(N-9-fluorenylmethoxycarbonyl)aminoethyl]-N-[6-(2-(pyridin-2yl)pyrimidine-4-carboxamido)hexanoyl]-glycine), have been synthesized as building blocks for Ru(II)-PNA oligomers and characterized by IR and H-1 NMR spectroscopy, mass spectrometry, electrochemistry and elemental analysis. As a proof of principle, M1 was incorporated on the solid phase within the PNA sequences H-g-c-a-a-t-a-a-a-a-Lys-NH2 (PNA1) and H-P-K-K-K-R-K-V-g-c-a-a-t-a-a-a-a-lys-NH2 (PNA4) to give PNA2(H-g-c-a-a-t-a-a-a-a-M1-lys-NH2) and PNA3 (H-P-K-K-K-R-K-V-g-c-a-a-t-a-a-a-a-M1-lys-NH2), respectively. The two Ru(II) PNA oligomers, PNA2 and PNA3, displayed a metal to ligand charge transfer (MLCT) transition band centered around 445 nm and an emission maximum at about 680 nm following 450 nm excitation in aqueous solutions (10 mM PBS, pH 7.4). The absorption and emission response, of the duplexes formed with the cDNA strand (DNA: 5'-T-T-T-T-T-T-T-A-T-T-G-C-T-T-T-3') showed no major Variations, suggesting that the electronic properties of the Ru(II) complexes are largely unaffected by hybridization. The thermal stability of the PNA center dot DNA duplexes, as evaluated from UV melting experiments, is enhanced compared to the corresponding nonmetalated duplexes. The melting temperature (T-m) was almost 8 degrees C higher for PNA2 center dot DNA duplex, and 4 degrees C for PNA3 center dot DNA duplex, with the stabilization attributed to the electrostatic interaction between the cationic residues (Ru(II) unit and positively charged lysine/arginine) and the polyanionic DNA backbone. In presence of tripropylamine (TPA) as co-reactant, PNA2, PNA3, PNA2 center dot DNA and PNA3 center dot DNA displayed strong electrochemiluminescence (ECL) signals even at submicromolar concentrations. Importantly, the combination of spectrochemical, thermal and ECL properties possessed by the Ru(II)-PNA sequences offer an elegant approach for the design of highly sensitive multimodal biosensing tools.