Diisopropyl-phosphoramidous acid (2R,3R,4R,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-(6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester methyl ester | 911128-69-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: Diisopropyl-phosphoramidous acid (2R,3R,4R,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-(6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester methyl ester
• CAS: 911128-69-3
• 化学式: C₄₄H₆₀N₅O₈PSi
• 分子量: 846.048
• InChiKey: RKXDJXSHKFALAT-PGHUPTSKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.81
• 重原子数：
  59.0
• 可旋转键数：
  17.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  131.42
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  Diisopropyl-phosphoramidous acid (2R,3R,4R,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-(6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester methyl ester 在 Amberlite IR-120 Plus sulfonic acid resin 、 三氟乙酸吡啶 作用下， 以 乙腈 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Polymorphism of the Signaling Molecule c-di-GMP

  摘要：

  Using UV, CD, and NMR, we demonstrate that the important bacterial signaling molecule involved in biofilm formation, cyclic diguanosine monophosphate (c-di-GMP), exists as a mixture of five different but related structures in an equilibrium that is sensitive both to its concentration and to the metal present. At the lower concentrations used for UV and CD work (0.05-0.5 mM), Li+, Na+, Cs+, and Mg2+ favor a bimolecular self-intercalated structure, while K+, Rb+, and NH4+ favor formation of one or more guanine quartet complexes as well. At the higher NMR concentrations (similar to 30 mM), the bimolecular structures associate and rearrange to a mixture of all-syn and all-anti tetramolecular and octamolecular quartet complexes. With K+ the octamolecular complexes predominate, while with Li+ the tetramolecular and octamolecular quartet complexes are present in approximately equal amounts, along with the bimolecular structure. We also find that both guanine amino groups in c-di-GMP are essential for formation of the quartets, because substitution of inosine for one guanosine allows formation of only the bimolecular structure. Further, two molecules of c-di-GMP tethered together are constrained in such a way that limits their ability to form these quartet complexes. The polymorphism we describe may provide different options for this signaling molecule when performing its functions in a bacterial cell, with K+ and its own local concentration controlling the equilibrium.

  DOI：

  10.1021/ja0613714
• 作为产物：
  描述：

  肌苷 在 咪唑 、 三氟乙酸吡啶 、 氟化氢吡啶 作用下， 以 吡啶 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.5h， 生成 Diisopropyl-phosphoramidous acid (2R,3R,4R,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-(6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester methyl ester
  参考文献：
  名称：

  Polymorphism of the Signaling Molecule c-di-GMP

  摘要：

  Using UV, CD, and NMR, we demonstrate that the important bacterial signaling molecule involved in biofilm formation, cyclic diguanosine monophosphate (c-di-GMP), exists as a mixture of five different but related structures in an equilibrium that is sensitive both to its concentration and to the metal present. At the lower concentrations used for UV and CD work (0.05-0.5 mM), Li+, Na+, Cs+, and Mg2+ favor a bimolecular self-intercalated structure, while K+, Rb+, and NH4+ favor formation of one or more guanine quartet complexes as well. At the higher NMR concentrations (similar to 30 mM), the bimolecular structures associate and rearrange to a mixture of all-syn and all-anti tetramolecular and octamolecular quartet complexes. With K+ the octamolecular complexes predominate, while with Li+ the tetramolecular and octamolecular quartet complexes are present in approximately equal amounts, along with the bimolecular structure. We also find that both guanine amino groups in c-di-GMP are essential for formation of the quartets, because substitution of inosine for one guanosine allows formation of only the bimolecular structure. Further, two molecules of c-di-GMP tethered together are constrained in such a way that limits their ability to form these quartet complexes. The polymorphism we describe may provide different options for this signaling molecule when performing its functions in a bacterial cell, with K+ and its own local concentration controlling the equilibrium.

  DOI：

  10.1021/ja0613714