6-Amino-9-[(2R,4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-1,9-dihydro-purin-2-one | 150668-67-0

• 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: 6-Amino-9-[(2R,4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-1,9-dihydro-purin-2-one
• CAS: 150668-67-0
• 化学式: C₂₂H₄₁N₅O₄Si₂
• 分子量: 495.77
• InChiKey: BKSZCGGJPPZLQJ-ARFHVFGLSA-N

物化性质

• 密度：
  1.18±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  33.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  117.28
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  6-Amino-9-[(2R,4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-1,9-dihydro-purin-2-one 在 四丁基氟化铵 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 32.5h， 生成 [9-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxyoxolan-2-yl]-6-[(E)-(dibutylamino)methylideneamino]purin-2-yl] N,N-diphenylcarbamate
  参考文献：
  名称：

  Theoretical and Experimental Study of Isoguanine and Isocytosine:  Base Pairing in an Expanded Genetic System

  摘要：

  The stabilities of all possible purine/pyrimidine pairings between the isomeric nucleobases isocytosine (iso-C) and isoguanine (iso-G) and standard genomic bases are reported for two independent oligonucleotide duplexes. Additionally, results are given from ab initio calculations performed on iso-C and iso-G. The calculations are used as an aid in the interpretation of thermodynamic data obtained from duplex denaturation studies. The unnatural iso-C/iso-G pair is found to be as stable as a C/G Watson-Crick pair in both duplex systems. The next most stable unnatural pair is that formed by C/iso-G and is observed to be isoenergetic with a U/A Watson-Crick Fair. Ab initio data suggest iso-G may adopt an unprecedented imino oxo tautomer which could explain the unusual stability of the C/iso-G pair. The stability of the other possible unnatural pairs are reported and similarly interpreted in terms of ab initio and other available experimental data. Finally, the fitness is discussed of a six-component genetic system that includes iso-C, iso-G, and four standard genomic bases.

  DOI：

  10.1021/ja970123s
• 作为产物：
  描述：

  9-((2R,4S,5R)-4-((叔丁基二甲基硅烷基)氧基)-5-(((叔丁基二甲基硅烷基)氧基)甲基)四氢呋喃-2-基)-9H-嘌呤-6-胺 在 间氯过氧苯甲酸 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 30.0h， 生成 6-Amino-9-[(2R,4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-1,9-dihydro-purin-2-one
  参考文献：
  名称：

  Theoretical and Experimental Study of Isoguanine and Isocytosine:  Base Pairing in an Expanded Genetic System

  摘要：

  The stabilities of all possible purine/pyrimidine pairings between the isomeric nucleobases isocytosine (iso-C) and isoguanine (iso-G) and standard genomic bases are reported for two independent oligonucleotide duplexes. Additionally, results are given from ab initio calculations performed on iso-C and iso-G. The calculations are used as an aid in the interpretation of thermodynamic data obtained from duplex denaturation studies. The unnatural iso-C/iso-G pair is found to be as stable as a C/G Watson-Crick pair in both duplex systems. The next most stable unnatural pair is that formed by C/iso-G and is observed to be isoenergetic with a U/A Watson-Crick Fair. Ab initio data suggest iso-G may adopt an unprecedented imino oxo tautomer which could explain the unusual stability of the C/iso-G pair. The stability of the other possible unnatural pairs are reported and similarly interpreted in terms of ab initio and other available experimental data. Finally, the fitness is discussed of a six-component genetic system that includes iso-C, iso-G, and four standard genomic bases.

  DOI：

  10.1021/ja970123s

文献信息

• Synthesis of oligonucleotides bearing the non-standard bases iso-C and iso-G. Comparison of iso-C-iso-G, C-G and U-A base-pair stabilities in RNA/DNA duplexes
  作者：Christopher Roberts、Rajanikanth Bandaru、Christopher Switzer

  DOI：10.1016/0040-4039(95)00603-a

  日期：1995.5

  The synthesis of iso-cytidine and 2′-deoxy-iso-guanosine phosphoramidites in protected form is described. The synthesis of complementary dodecanucleotides containing a central iso-C-iso-G base-pair was achieved. It is found that the iso-C-iso-G base-pair has comparable stability to a C-G base-pair.

  描述了保护形式的异胞苷和2'-脱氧-异鸟苷亚磷酰胺的合成。实现了包含中心异-C-异-G碱基对的互补十二核苷酸的合成。发现iso -C- iso -G碱基对具有与CG碱基对相当的稳定性。
• Anion mediated, tunable isoguanosine self-assemblies: decoding the conformation influence and solvent effects
  作者：Mengjia Liu、Ying He、Chuan Shan、Lukasz Wojtas、Ion Ghiviriga、Omar Fathalla、Yu Yan、Xiaopeng Li、Xiaodong Shi

  DOI：10.1039/d1sc00988e

  日期：——

  derivatives. Based on this observation, deoxy isoG derivative with modification on ribose (tert-butyldimethylsilyl ether) was applied to assemble with the Cs+ cation. Critical solvent (CDCl3 and CD3CN) and anion (BPh4−, BARF−, and PF6−) effects were revealed, leading to the controllable formation of various stable isoG pentaplexes, including singly charged decamer, doubly charged decamer, and 15-mer, etc. Finally

  对 C8 嘌呤和核糖的各种取代基进行了系统研究。合成了一系列isoG类似物，即C8-苯基取代的isoG，并应用于Cs +配位。嘌呤和核糖之间的结构接近性限制了 C8-苯基取代的 isoG 衍生物的五聚体形成。基于这一观察，采用核糖修饰的脱氧isoG衍生物（叔丁基二甲基甲硅烷基醚）与Cs +阳离子组装。揭示了临界溶剂（CDCl 3和 CD 3 CN）和阴离子（BPh 4 - 、BARF -和 PF 6 - ）效应，导致可控形成各种稳定的 isoG 五聚体，包括单电荷十聚体、双电荷十聚体和最终成功获得了[isoG 20 Cs 3 ] 3+ (BARF - ) 3的X射线晶体结构，这是第一个多层脱氧isoG与Cs +阳离子结合的例子，为这种新型 isoG 离子载体超越两层夹心自组装提供了坚实的证据。
• 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。