3'-amino-3'-deoxy-3'-[(3''R)-N-Fmoc-3''-fluoro-L-phenylalanyl]-N(6),N(6)-dimethyladenosine | 1132645-31-8

• 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'-amino-3'-deoxy-3'-[(3''R)-N-Fmoc-3''-fluoro-L-phenylalanyl]-N(6),N(6)-dimethyladenosine
• CAS: 1132645-31-8
• 化学式: C₃₆H₃₆FN₇O₆
• 分子量: 681.724
• InChiKey: RGHDEKGOBSOYRD-CQSVWHOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.25
• 重原子数：
  50.0
• 可旋转键数：
  10.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  163.96
• 氢给体数：
  4.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  3'-amino-3'-deoxy-3'-[(3''R)-N-Fmoc-3''-fluoro-L-phenylalanyl]-N(6),N(6)-dimethyladenosine 在 吡啶 、 三(2-氨基乙基)胺 作用下， 反应 4.0h， 以100%的产率得到3'-amino-3'-deoxy-3'-[(3''R)-3''-fluoro-L-phenylalanyl]-N(6),N(6)-dimethyladenosine
  参考文献：
  名称：

  Synthesis of a Fluorine-Substituted Puromycin Derivative for Brønsted Studies of Ribosomal-Catalyzed Peptide Bond Formation

  摘要：

  The mechanism by which the ribosome catalyzes peptide bond formation remains controversial, Here we describe the synthesis of a nucleoside that can be used in Bronsted experiments to assess the transition state of ribosome catalyzed peptide bond formation. This substrate is the nucleoside 3'-amino-3'-deoxy-3'-[(3"R)-3-fluoro-L-phenylalanyl]-N(6),N(6)-dimethyladenosine, which was prepared from (1R,2R)-2-amino-1-phenylpropane-1,3-diol. This substrate is active in peptide bond formation on the ribosome and is a useful probe for Bronsted analysis experiments on the ribosome.

  DOI：

  10.1021/jo802611t
• 作为产物：
  描述：

  (3R)-N-Fmoc-3-fluoro-L-phenylalanine 、 氨基核苷嘌呤霉素 在 N,N-二异丙基乙胺 、 N,N-二甲基甲酰胺 、 bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以78%的产率得到3'-amino-3'-deoxy-3'-[(3''R)-N-Fmoc-3''-fluoro-L-phenylalanyl]-N(6),N(6)-dimethyladenosine
  参考文献：
  名称：

  Synthesis of a Fluorine-Substituted Puromycin Derivative for Brønsted Studies of Ribosomal-Catalyzed Peptide Bond Formation

  摘要：

  The mechanism by which the ribosome catalyzes peptide bond formation remains controversial, Here we describe the synthesis of a nucleoside that can be used in Bronsted experiments to assess the transition state of ribosome catalyzed peptide bond formation. This substrate is the nucleoside 3'-amino-3'-deoxy-3'-[(3"R)-3-fluoro-L-phenylalanyl]-N(6),N(6)-dimethyladenosine, which was prepared from (1R,2R)-2-amino-1-phenylpropane-1,3-diol. This substrate is active in peptide bond formation on the ribosome and is a useful probe for Bronsted analysis experiments on the ribosome.

  DOI：

  10.1021/jo802611t