3'N-[[(2S)-2-tert-butyldimethylsilyloxy-3-phenyl-1-oxopropyl]amino]-3'-deoxy-N6,N6-dimethyladenosine | 699021-37-9

• 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: 3'N-[[(2S)-2-tert-butyldimethylsilyloxy-3-phenyl-1-oxopropyl]amino]-3'-deoxy-N6,N6-dimethyladenosine
• 英文别名: 3'N-[[(2S)-2-tert-butyldimethylsilyloxy-3-phenyl-1-oxopropyl]amino]-3'-deoxy-N⁶,N⁶-dimethyladenosine
• CAS: 699021-37-9
• 化学式: C₂₇H₄₀N₆O₅Si
• 分子量: 556.737
• InChiKey: LJKUQXUFIIJGTO-HOEDKODCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.26
• 重原子数：
  39.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  134.86
• 氢给体数：
  3.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  3'N-[[(2S)-2-tert-butyldimethylsilyloxy-3-phenyl-1-oxopropyl]amino]-3'-deoxy-N6,N6-dimethyladenosine 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 41.0h， 生成
  参考文献：
  名称：

  Regiospecificity of the Peptidyl tRNA Ester within the Ribosomal P Site

  摘要：

  The ribosomal peptidyl transferase center is expected to be regiospecific with regard to its tRNA substrates, yet the ester linkages between the tRNA and the amino acid or peptide are susceptible to isomerization between the O2' and O3' hydroxyls of the terminal A76 ribose sugar. To establish which isomer of the P site tRNA ester is utilized by the ribosome, we prepared two nonisomerizable transition state inhibitors with either an A76 O2' or O3' linkage. Strong preferential binding to the O3' regioisomer indicates that the peptidyl transferase proceeds through a transition state with an O3'-linked peptide in the P-site.

  DOI：

  10.1021/ja0554099
• 作为产物：
  描述：

  (2S)-2-(tert-butyldimethylsilyloxy)-3-phenylpropanoyl chloride 、 氨基核苷嘌呤霉素 在 吡啶 、 三甲基氯硅烷 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以82%的产率得到3'N-[[(2S)-2-tert-butyldimethylsilyloxy-3-phenyl-1-oxopropyl]amino]-3'-deoxy-N6,N6-dimethyladenosine
  参考文献：
  名称：

  Regiospecificity of the Peptidyl tRNA Ester within the Ribosomal P Site

  摘要：

  The ribosomal peptidyl transferase center is expected to be regiospecific with regard to its tRNA substrates, yet the ester linkages between the tRNA and the amino acid or peptide are susceptible to isomerization between the O2' and O3' hydroxyls of the terminal A76 ribose sugar. To establish which isomer of the P site tRNA ester is utilized by the ribosome, we prepared two nonisomerizable transition state inhibitors with either an A76 O2' or O3' linkage. Strong preferential binding to the O3' regioisomer indicates that the peptidyl transferase proceeds through a transition state with an O3'-linked peptide in the P-site.

  DOI：

  10.1021/ja0554099