2-N-isobutyryl-2'-O-tert-butyldimethylsilyl-P-thioguanosinylyl (3'->5')-2-N-isobutyryl-2'-O-tert-butyldimethylsilyl-3'-O-(H-phosphonate)-guanosine sodium salt | 1259874-33-3

• 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: 2-N-isobutyryl-2'-O-tert-butyldimethylsilyl-P-thioguanosinylyl (3'->5')-2-N-isobutyryl-2'-O-tert-butyldimethylsilyl-3'-O-(H-phosphonate)-guanosine sodium salt
• CAS: 1259874-33-3
• 化学式: C₄₃H₆₈N₁₁O₁₅P₂SSi₂*Na
• 分子量: 1152.25
• InChiKey: RIASQERNLFGKNV-YOLOIVFESA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.71
• 重原子数：
  75.0
• 可旋转键数：
  21.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  343.33
• 氢给体数：
  5.0
• 氢受体数：
  23.0

反应信息

• 作为反应物：
  描述：

  2-N-isobutyryl-2'-O-tert-butyldimethylsilyl-P-thioguanosinylyl (3'->5')-2-N-isobutyryl-2'-O-tert-butyldimethylsilyl-3'-O-(H-phosphonate)-guanosine sodium salt 在 吡啶 、 三甲基乙酰氯 、 水 、 碘 作用下， 反应 0.13h， 生成
  参考文献：
  名称：

  Thiophosphate Analogs of c-di-GMP: Impact on Polymorphism

  摘要：

  Seven phosphorothioate analogs of c-di-GMP (all diastereomers of mono-, di-, and trithiophosphates) were prepared to assess the impact of the thioate substitutions on c-di-GMP polymorphism using 1D H-1 and P-31 NMR, along with 2D NOESY and DOSY, for both the Na+ and K+ salts. The K+ salts display more extensive higher order complex formation than the Na+ salts, resulting primarily in octamolecular complexes with K+, but tetramolecular complexes with Na+. Further, the presence of one or two [S-P] sulfurs specifically stabilizes anti complexes and/or destabilizes syn complexes, while the presence of two [S-P] sulfurs Promotes extensive aggregation.

  DOI：

  10.1080/15257770903044523
• 作为产物：
  描述：

  在 NaHSO₄/SiO₂ 作用下， 以 二氯甲烷 为溶剂， 生成 2-N-isobutyryl-2'-O-tert-butyldimethylsilyl-P-thioguanosinylyl (3'->5')-2-N-isobutyryl-2'-O-tert-butyldimethylsilyl-3'-O-(H-phosphonate)-guanosine sodium salt
  参考文献：
  名称：

  Thiophosphate Analogs of c-di-GMP: Impact on Polymorphism

  摘要：

  Seven phosphorothioate analogs of c-di-GMP (all diastereomers of mono-, di-, and trithiophosphates) were prepared to assess the impact of the thioate substitutions on c-di-GMP polymorphism using 1D H-1 and P-31 NMR, along with 2D NOESY and DOSY, for both the Na+ and K+ salts. The K+ salts display more extensive higher order complex formation than the Na+ salts, resulting primarily in octamolecular complexes with K+, but tetramolecular complexes with Na+. Further, the presence of one or two [S-P] sulfurs specifically stabilizes anti complexes and/or destabilizes syn complexes, while the presence of two [S-P] sulfurs Promotes extensive aggregation.

  DOI：

  10.1080/15257770903044523

文献信息

• SYNTHESIS OF CYCLIC DIGUANOSINE MONOPHOSPHATE AND THIOPHOSPHATE ANALOGS THEREOF
  申请人：Jones Roger A.

  公开号：US20120178710A1

  公开（公告）日：2012-07-12

  The invention provides methods for the synthesis of cyclic dinucleotides and thiophosphate analogs thereof as well as a new family of analogs of cyclic diguanosine monophosphate that includes a series of seven phosphorothioate derivatives that includes diastereomers of mono-, di-, and trithiophosphates.

  本发明提供了合成环状双核苷酸及其硫代磷酸酯类似物的方法，以及包含一系列七个硫代磷酸酯衍生物的环状二鸟苷酸单磷酸酯的新类似物，其中包括单硫、双硫和三硫磷酸酯的对映异构体。