succinic acid mono-(6-(2-(3-butyl-ureido)-6-oxo-1,6-dihydro-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl) ester | 873795-55-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: succinic acid mono-(6-(2-(3-butyl-ureido)-6-oxo-1,6-dihydro-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl) ester
• 英文别名: 4-[[(3aR,4R,6R,6aR)-4-[2-(butylcarbamoylamino)-6-oxo-1H-purin-9-yl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methoxy]-4-oxobutanoic acid
• CAS: 873795-55-2
• 化学式: C₂₂H₃₀N₆O₉
• 分子量: 522.515
• InChiKey: SRKWGNBRRDNMRK-LUTMRVPUSA-N

物化性质

• 熔点：
  214-217 °C(Solv: chloroform (67-66-3); methanol (67-56-1))
• 密度：
  1.62±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  37
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  192
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  succinic acid mono-(6-(2-(3-butyl-ureido)-6-oxo-1,6-dihydro-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl) ester 、 甲基丙烯酸羟乙酯 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以71%的产率得到succinic acid 6-[2-(3-butyl-ureido)-6-oxo-1,6-dihydro-purin-9-yl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester 2-(2-methyl-acryloyloxy)-ethyl ester
  参考文献：
  名称：

  Formation of a Miscible Supramolecular Polymer Blend through Self-Assembly Mediated by a Quadruply Hydrogen-Bonded Heterocomplex

  摘要：

  A supramolecular network polymer consisting of a pair of immiscible polymers, poly( butyl)methacrylate ( PBMA) and polystyrene ( PS), is described. A urea of guanosine ( 1, UG) and 2,7-diamido1,8-naphthyridine ( 2, DAN), which form an exceptionally strong quadruply hydrogen-bonding complex, are displayed at 1-10 mol % along the main backbone of PBMA and PS, respectively. H-1 NMR studies show heterocomplexation between UG and DAN exclusively. This high-fidelity, high- affinity supramolecular connection of two different polymer coils at the molecular level produces a polymer blend. Blends containing different weight ratios of the polymers and mole percent of the recognition units were characterized by AFM and DSC experiments with no isolated domains observed and a single glass-transition temperature ( T-g). The T-g is tunable by varying the weight ratio of the polymers in the blend. In addition, viscosity measurements, size-exclusion chromatography ( SEC), and dynamic light-scattering ( DLS) studies demonstrate the formation of a supramolecular network structure.

  DOI：

  10.1021/ja0631854
• 作为产物：
  描述：

  鸟苷 在 4-二甲氨基吡啶 、 sodium methylate 、 sodium hydride 、 对甲苯磺酸 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 丙酮 、 乙腈 为溶剂， 反应 27.0h， 生成 succinic acid mono-(6-(2-(3-butyl-ureido)-6-oxo-1,6-dihydro-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl) ester
  参考文献：
  名称：

  A Quadruply Hydrogen Bonded Heterocomplex Displaying High-Fidelity Recognition

  摘要：

  An exceptionally strong quadruply hydrogen-bonded complex is formed between 2,7-diamido-1,8-naphthyridine 3 (DAN) and the butylurea of guanosine 6 (UG) in chloroform. The UG unit can be prepared in four steps from guanosine on a 10 g scale in excellent yields without chromatographic purification. The association constant (K-assoc approximate to 5 x 10(7) m(-1)) for the UG(.)DAN complex determined by fluorescence energy transfer from the naphthyridine unit of 3 to coumarin 343 covalently linked UG (18) is among the highest reported for a neutral DNA base-pair analogue. The weak self-association of DAN (K-dimer < 10 m(-1)) and UG (K-dimer ca. 200-300 m(-1)) means that the UG-DAN complex forms with unparalleled fidelity.

  DOI：

  10.1021/ja0545517

文献信息

• A Supramolecular Multi-Block Copolymer with a High Propensity for Alternation
  作者：Taiho Park、Steven C. Zimmerman

  DOI：10.1021/ja064116s

  日期：2006.11.1

  Alternating, multi-block supramolecular copolymers were created using quadruple hydrogen bonding as the noncovalent binding force. One block consisted of two guanosine butyl urea (UG) units attached at the ends of a triethylene glycol linker or a PEG chain (MW = 2 kD). The other block contained a 2,7-diamido-1,8-naphthyridine (DAN) unit at each end of a short alkane diester linker or a 100 kD poly(butyl methacrylate) macromolecule. The UG unit presents an ADDA hydrogen bonding array that is complementary to the DAAD array of DAN, and these form a very strong complex (Kassoc approximately 5 x 107 M-1), whereas UG and DAN weakly self-associate. These recognition properties allowed a multi-block supramolecular polymer to form which exhibits a high propensity for alternation. The self-assembled polymeric structure was shown to be reversibly formed and it was characterized by a combination of dynamic light scattering (DLS), 1H NMR, size exclusion chromatography (SEC), and viscometry.
• A Quadruply Hydrogen Bonded Heterocomplex Displaying High-Fidelity Recognition
  作者：Taiho Park、Eric M. Todd、Shoji Nakashima、Steven C. Zimmerman

  DOI：10.1021/ja0545517

  日期：2005.12.1

  An exceptionally strong quadruply hydrogen-bonded complex is formed between 2,7-diamido-1,8-naphthyridine 3 (DAN) and the butylurea of guanosine 6 (UG) in chloroform. The UG unit can be prepared in four steps from guanosine on a 10 g scale in excellent yields without chromatographic purification. The association constant (K-assoc approximate to 5 x 10(7) m(-1)) for the UG(.)DAN complex determined by fluorescence energy transfer from the naphthyridine unit of 3 to coumarin 343 covalently linked UG (18) is among the highest reported for a neutral DNA base-pair analogue. The weak self-association of DAN (K-dimer < 10 m(-1)) and UG (K-dimer ca. 200-300 m(-1)) means that the UG-DAN complex forms with unparalleled fidelity.
• Formation of a Miscible Supramolecular Polymer Blend through Self-Assembly Mediated by a Quadruply Hydrogen-Bonded Heterocomplex
  作者：Taiho Park、Steven C. Zimmerman

  DOI：10.1021/ja0631854

  日期：2006.9.1

  A supramolecular network polymer consisting of a pair of immiscible polymers, poly( butyl)methacrylate ( PBMA) and polystyrene ( PS), is described. A urea of guanosine ( 1, UG) and 2,7-diamido1,8-naphthyridine ( 2, DAN), which form an exceptionally strong quadruply hydrogen-bonding complex, are displayed at 1-10 mol % along the main backbone of PBMA and PS, respectively. H-1 NMR studies show heterocomplexation between UG and DAN exclusively. This high-fidelity, high- affinity supramolecular connection of two different polymer coils at the molecular level produces a polymer blend. Blends containing different weight ratios of the polymers and mole percent of the recognition units were characterized by AFM and DSC experiments with no isolated domains observed and a single glass-transition temperature ( T-g). The T-g is tunable by varying the weight ratio of the polymers in the blend. In addition, viscosity measurements, size-exclusion chromatography ( SEC), and dynamic light-scattering ( DLS) studies demonstrate the formation of a supramolecular network structure.