2',3',5'-tris((tert-butyldimethylsilyl)oxy)-8-benzyloxyguanosine | 151566-06-2

• 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: 2',3',5'-tris((tert-butyldimethylsilyl)oxy)-8-benzyloxyguanosine
• 英文别名: 2-amino-9-[(2R,3R,4R,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]-8-phenylmethoxy-1H-purin-6-one
• CAS: 151566-06-2
• 化学式: C₃₅H₆₁N₅O₆Si₃
• 分子量: 732.156
• InChiKey: FLUOFJPAXZFRQO-BQOYKFDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.98
• 重原子数：
  49
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  131
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2',3',5'-tris((tert-butyldimethylsilyl)oxy)-8-benzyloxyguanosine 在 palladium dihydroxide 氢气 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以87%的产率得到2',3',5'-tris-(O-tert-butyldimethylsilyl)-8-oxo-7,8-dihydroguanosine
  参考文献：
  名称：

  Reactivity toward Singlet Oxygen of a 7,8-Dihydro-8-oxoguanosine ("8-Hydroxyguanosine") Formed by Photooxidation of a Guanosine Derivative

  摘要：

  Total quenching (k(r) + k(q)) and chemical reaction rates (k(r)) for the removal of singlet oxygen by 2,3',5'-tris((tert-butyldimethylsilyl)oxy)guanos (1) and its oxidation product, 2',3',5'-tris((tert-butyldimethylsilyl)oxy)-7,8-dihydro-8-oxoguanosine (2), were determined by the time-resolved infrared luminescence technique and competition experiments, respectively. Compound 2 is two orders of magnitude more reactive with singlet oxygen than 1. A mechanism for the formation of 2 from 1 with singlet oxygen is proposed.

  DOI：

  10.1021/ja00129a004
• 作为产物：
  描述：

  鸟苷 在 咪唑 、 溴 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 114.0h， 生成 2',3',5'-tris((tert-butyldimethylsilyl)oxy)-8-benzyloxyguanosine
  参考文献：
  名称：

  Reactivity toward Singlet Oxygen of a 7,8-Dihydro-8-oxoguanosine ("8-Hydroxyguanosine") Formed by Photooxidation of a Guanosine Derivative

  摘要：

  Total quenching (k(r) + k(q)) and chemical reaction rates (k(r)) for the removal of singlet oxygen by 2,3',5'-tris((tert-butyldimethylsilyl)oxy)guanos (1) and its oxidation product, 2',3',5'-tris((tert-butyldimethylsilyl)oxy)-7,8-dihydro-8-oxoguanosine (2), were determined by the time-resolved infrared luminescence technique and competition experiments, respectively. Compound 2 is two orders of magnitude more reactive with singlet oxygen than 1. A mechanism for the formation of 2 from 1 with singlet oxygen is proposed.

  DOI：

  10.1021/ja00129a004

文献信息

• Structure-based design of guanosine analogue inhibitors targeting GTP cyclohydrolase IB towards a new class of antibiotics
  作者：George N. Samaan、Naduni Paranagama、Ayesha Haque、David A. Hecht、Manal A. Swairjo、Byron W. Purse

  DOI：10.1016/j.bmcl.2019.126818

  日期：2020.1

  distinct from the human homologue GCYH-IA. A comparison of the crystal structures of GCYH-IA and -IB with the nM inhibitor 8-oxo-GTP bound shows that the active site of GCYH-IB is larger and differently shaped. Based on this structural information, we designed and synthesized a small set of 8-oxo-G derivatives with ether linkages at O6 and O8 expected to displace water molecules from the expanded active

  GTP环水解酶（GCYH-I）是叶酸生物合成途径中的一种酶，以前尚未被用作抗生素靶标，尽管包括淋病奈瑟菌在内的几种病原体都使用某种形式的GCYH-IB酶，其结构与人的同源基因不同GCYH-IA。GCYH-IA和-IB与nM抑制剂8-oxo-GTP结合的晶体结构的比较表明，GCYH-IB的活性位点更大且形状不同。基于此结构信息，我们设计和合成了少量的在O6和O8带有醚键的8-氧代-G衍生物，这些衍生物有望将水分子从GCYH-IB的扩展活性位点转移出来。这些化合物中最有效的G3对GCYH-IB具有选择性，
• Reactivity toward Singlet Oxygen of a 7,8-Dihydro-8-oxoguanosine ("8-Hydroxyguanosine") Formed by Photooxidation of a Guanosine Derivative
  作者：Chimin Sheu、Christopher S. Foote

  DOI：10.1021/ja00129a004

  日期：1995.6

  Total quenching (k(r) + k(q)) and chemical reaction rates (k(r)) for the removal of singlet oxygen by 2,3',5'-tris((tert-butyldimethylsilyl)oxy)guanos (1) and its oxidation product, 2',3',5'-tris((tert-butyldimethylsilyl)oxy)-7,8-dihydro-8-oxoguanosine (2), were determined by the time-resolved infrared luminescence technique and competition experiments, respectively. Compound 2 is two orders of magnitude more reactive with singlet oxygen than 1. A mechanism for the formation of 2 from 1 with singlet oxygen is proposed.