O2',O3'-isopropylidene-isoguanosine | 17651-21-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: O2',O3'-isopropylidene-isoguanosine
• 英文别名: 2',3'-O-Isopropylideneisoguanosine
• CAS: 17651-21-7
• 化学式: C₁₃H₁₇N₅O₅
• 分子量: 323.308
• InChiKey: GWJAXOBGHZUWCA-IOSLPCCCSA-N

物化性质

• 熔点：
  241-243 °C(Solv: water (7732-18-5))
• 密度：
  1.93±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.48
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  137.77
• 氢给体数：
  3.0
• 氢受体数：
  10.0

文献信息

• Modular Construction of Dynamic Nucleodendrimers
  作者：Valentina Abet、Robert Evans、Florian Guibbal、Stefano Caldarelli、Raphaël Rodriguez

  DOI：10.1002/anie.201402400

  日期：2014.5.5

  Isoguanosine‐containing dendritic small molecules self‐assemble into decameric nucleodendrimers as observed by 1D NMR spectroscopy, 2D DOSY, and mass spectrometry. In particular, apolar building blocks readily form pentameric structures in acetonitrile while the presence of alkali metals promotes the formation of stable decameric assemblies with a preference for cesium ions. Remarkably, co‐incubation

  通过1D NMR光谱，2D DOSY和质谱法观察到，含有异鸟苷的树枝状小分子会自组装成十聚体的核树枝状大分子。特别是，非极性结构单元很容易在乙腈中形成五聚体结构，而碱金属的存在促进了稳定的十聚体组装的形成，偏爱铯离子。值得注意的是，鸟苷和含异鸟苷的核糖核酸的共孵育会导致在不添加盐的情况下形成十聚体结构。对该混合物的进一步分析表明鸟苷衍生物有助于形成，但不参与十聚体结构。一个让人想起分子拥挤的过程。该分子系统为多功能树突状大分子的快速模块化组装提供了强大的平台。
• Nucleosides XII.¹Synthesis of 5-Modified Isoguanosines and Reinvestigation of 5′-Deoxy-<i>N³</i>,5′-cycloisoguanosine
  作者：Tun-Cheng Chien、Chia-Chi Kuo、Chien-Shu Chen、Ji-Wang Chern

  DOI：10.1002/jccs.200400205

  日期：2004.12

  its 6-amino group was protected by N,N-dimethylaminomethylidene. The synthesis of 5-deoxyN 3 ,5-cycloisoguanosine (6) and its 2,3-O-isopropylidene derivative (11) were accomplished in excellent yields from isoguanosines (3 & 10) in the presence of triphenylphospine and carbon tetrachloride in pyridine. Chlorination at the 5-position of isoguanosine (3) with thionyl chloride followed by the aqueous basepromoted

  当异鸟苷(3) 的6-氨基被N,N-二甲基氨基亚甲基保护时，异鸟苷(3) 在三正丁基膦存在下与二芳基二硫化物发生偶联反应。5-脱氧N 3 ,5-环异鸟苷 (6) 及其 2,3-O-异亚丙基衍生物 (11) 的合成是在三苯基膦和四氯化碳在吡啶中的存在下以优异的产率由异鸟苷 (3 和 10) 完成的。用亚硫酰氯在异鸟苷 (3) 的 5 位氯化，然后用水碱促进环化，得到相同的产物 6。通过包括 IR、UV、1-D 和 2-D NMR 的光谱分析来阐明结构。
• Design and synthesis of covalently tethered “isoG-star” as a recyclable host for selective cesium separation
  作者：Mengjia Liu、Ying He、Lukasz Wojtas、Xiaodong Shi

  DOI：10.1039/d3gc02932h

  日期：——

  application of this newly developed covalently linked isoG-star enabled selective Cs+ extraction, followed by controlled solvent-induced H-bond dissociation. This resulted in the creation of a recyclable Cs+ extractor, demonstrating excellent cation selectivity and good reusability (over seven cycles) for the first time. Consequently, this new supramolecular macrocycle offers a practical new platform for

  异鸟苷自组装五聚体 （isoG-star） 对竞争性碱和碱土金属阳离子的 Cs+ 结合表现出显著的选择性，使其成为放射性废物 137Cs 分离的有前途的萃取剂。然而，要使 isoG-star 成为 Cs+ 隔离的实用材料，需要开发一种可回收的 isoG-star 材料。在这项研究中，对功能性 isoG 衍生物进行了系统筛选。通过采用明确定义的复合物形成和组装后修饰，利用设计的 isoG 单体，通过烯烃复分解制备共价栓系 isoG5-star。这种新开发的共价连接的 isoG-star 的应用实现了选择性 Cs+ 提取，然后是受控的溶剂诱导的 H 键解离。这导致了可回收 Cs+ 萃取剂的诞生，首次表现出出色的阳离子选择性和良好的可重复使用性（超过 7 个循环）。因此，这种新的超分子大环为以环保和高效的方式治疗放射性铯 （134Cs 和 137Cs） 提供了一个实用的新平台。
• Self-Assembled Ionophores from Isoguanosine
  作者：Jeffery T. Davis、Sampath Tirumala、James R. Jenssen、Eric Radler、Dan Fabris

  DOI：10.1021/jo00118a038

  日期：1995.6

  The isoguanosine (isoG) mononucleoside 3 forms a C-4-symmetric tetramer in organic solvents. The isoG tetramer 6 has been characterized by 2D NMR spectroscopy, UV spectroscopy, and FAB mass spectrometry. Specific NOEs between the exocyclic C6NH2 amino protons and the ribose H1' and H2' protons confirmed the isoG self-association and was the basis for the tetramer model. Molecular models of isoG dimers, trimers, and tetramers show that only the C-4-symmetric tetramer 6 is consistent with the observed NH6-H1', H2' NOEs. In the isoG tetramer, hydrogen bonds between C6NHA and a purine NS bring both exocyclic amino protons within 3-4 Angstrom of the adjacent monomer's ribose H1' and H2' protons. The isoG tetramer 6 organizes by hydrogen bonding between the Watson-Crick face of one isoG base and the complementary bottom edge of another purine. The tetramer is stabilized by an inner and outer ring of hydrogen bonds. The inner ring forms between the imino NH1 proton of one monomer and the C2 carbonyl oxygen of an adjacent monomer, while the outer ring is made up of four NH6-N3 hydrogen bonds. The isoG tetramer is thermodynamically very stable, with a K-s of ca. 10(9)-10(10) M(-3) at room temperature, and a Delta G degrees of tetramer formation of -12.5 kcal mol(-1) in d(6)-acetone at 25 degrees C. The van't Hoff plots indicated that the thermodynamic parameters for tetramer formation were Delta H degrees = -18.2 kcal mol(-1) and Delta S degrees(298) = -19.1 eu Each isoG C2 oxygen in the tetramer has a nonbonded electron pair that points into a central cavity, enabling selective cation coordination. Solutions of the isoG mononucleoside 3 in d(6)-acetone were titrated with LiCl, NaI, KI, and BaI2. Each of these ions had a dramatic effect on the isoG structural equilibrium. Thus, Li+ destabilized the tetramer and shifted the equilibrium back to the monomer. Low concentrations of Na+, on the other hand, stabilized the tetramer. Titrations of solutions of isoG 3 with the larger cations, K+ and Ba+2, indicated that 1 equiv of metal coordinated 8 nucleotide monomers, suggesting formation of a metal-stabilized octamer. The NMR analysis indicates that the isoG-K+ tetramer 6 is much more stable than the corresponding guanosine-K+ complex.
• Divakar, K. J.; Mottahedeh, Mina; Reese, Colin B., Journal of the Chemical Society. Perkin transactions I, 1991, # 4, p. 771 - 774
  作者：Divakar, K. J.、Mottahedeh, Mina、Reese, Colin B.、Sanghvi, Yogesh S.、Swift, Karl A. D.

  DOI：——

  日期：——