guanosine 3',5'-cyclic([Sp]-{4-[N,N-bis(carboxymethyl)carbamoyl]-2-nitrophenyl}methyl) phosphate

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷酸
• 英文名称: guanosine 3',5'-cyclic([Sp]-{4-[N,N-bis(carboxymethyl)carbamoyl]-2-nitrophenyl}methyl) phosphate
• 英文别名: 2-[[4-[[(2R,4aR,6R,7R,7aS)-6-(2-amino-6-oxo-1H-purin-9-yl)-7-hydroxy-2-oxo-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-2-yl]oxymethyl]-3-nitrobenzoyl]-(carboxymethyl)amino]acetic acid
• 化学式: C₂₂H₂₂N₇O₁₄P
• 分子量: 639.429
• InChiKey: AONRJSYJLODJBF-ZNCYFATISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.9
• 重原子数：
  44
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  300
• 氢给体数：
  5
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  guanosine 3',5'-cyclic([Sp]-{4-[N,N-bis(carboxymethyl)carbamoyl]-2-nitrophenyl}methyl) phosphate 以 水 为溶剂， 生成 cyclic guanosine 3',5'-monophosphate 、 [Carboxymethyl-(4-hydroxymethyl-3-nitro-benzoyl)-amino]-acetic acid
  参考文献：
  名称：

  Photolabile Precursors of Cyclic Nucleotides with High Aqueous Solubility and Stability

  摘要：

  Photolabile phosphotriester derivatives of cyclic AMP and cyclic GMP are described, where the additional group on the phosphate is a 2-nitrobenzyl that bears an electron-withdrawing and dianionic substituent, This confers high aqueous solubility and excellent resistance to hydrolysis of the phosphotriester (t(1/2) for hydrolysis at pH 7, 22 degreesC, is > 3 months for the axial isomers 3a and 4a and > 1 month for the equatorial isomers 3b and 4b), The photolysis quantum yields are in the range 0.15-0.24, and the product release rate upon flash photolysis is 1.7 s(-1) at pH 7.0, 20 degreesC.

  DOI：

  10.1021/jo020040g
• 作为产物：
  描述：

  N-(4-(bromomethyl)-3-nitrobenzoyl)iminodiacetic acid bis[2-(trimethylsilyl)ethyl] ester 、 triethylammonium salt of cGMP 在 sodium carbonate 、 三氟乙酸 作用下， 以 乙醇 、 N,N-二甲基乙酰胺 为溶剂， 反应 0.5h， 生成 guanosine 3',5'-cyclic([Sp]-{4-[N,N-bis(carboxymethyl)carbamoyl]-2-nitrophenyl}methyl) phosphate 、 guanosine 3',5'-cyclic([Rp]-{4-[N,N-bis(carboxymethyl)carbamoyl]-2-nitrophenyl}methyl) phosphate
  参考文献：
  名称：

  Photolabile Precursors of Cyclic Nucleotides with High Aqueous Solubility and Stability

  摘要：

  Photolabile phosphotriester derivatives of cyclic AMP and cyclic GMP are described, where the additional group on the phosphate is a 2-nitrobenzyl that bears an electron-withdrawing and dianionic substituent, This confers high aqueous solubility and excellent resistance to hydrolysis of the phosphotriester (t(1/2) for hydrolysis at pH 7, 22 degreesC, is > 3 months for the axial isomers 3a and 4a and > 1 month for the equatorial isomers 3b and 4b), The photolysis quantum yields are in the range 0.15-0.24, and the product release rate upon flash photolysis is 1.7 s(-1) at pH 7.0, 20 degreesC.

  DOI：

  10.1021/jo020040g

文献信息

• Photolabile Precursors of Cyclic Nucleotides with High Aqueous Solubility and Stability
  作者：Lijuan Wang、John E. T. Corrie、John F. Wootton

  DOI：10.1021/jo020040g

  日期：2002.5.1

  Photolabile phosphotriester derivatives of cyclic AMP and cyclic GMP are described, where the additional group on the phosphate is a 2-nitrobenzyl that bears an electron-withdrawing and dianionic substituent, This confers high aqueous solubility and excellent resistance to hydrolysis of the phosphotriester (t(1/2) for hydrolysis at pH 7, 22 degreesC, is > 3 months for the axial isomers 3a and 4a and > 1 month for the equatorial isomers 3b and 4b), The photolysis quantum yields are in the range 0.15-0.24, and the product release rate upon flash photolysis is 1.7 s(-1) at pH 7.0, 20 degreesC.