3'-amino-3'-deoxy-3'-[(3''R)-3''-fluoro-L-phenylalanyl]-N(6),N(6)-dimethyladenosine | 1132645-32-9

• 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'-amino-3'-deoxy-3'-[(3''R)-3''-fluoro-L-phenylalanyl]-N(6),N(6)-dimethyladenosine
• 英文别名: (2R,3R)-2-amino-N-[(2S,3S,4R,5R)-5-[6-(dimethylamino)purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-3-fluoro-3-phenylpropanamide
• CAS: 1132645-32-9
• 化学式: C₂₁H₂₆FN₇O₄
• 分子量: 459.48
• InChiKey: WGTUFSYURVZQIL-URTVDEHISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  152
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为产物：
  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

文献信息

• Synthesis of a Fluorine-Substituted Puromycin Derivative for Brønsted Studies of Ribosomal-Catalyzed Peptide Bond Formation
  作者：Kensuke Okuda、Takashi Hirota、David A. Kingery、Hideko Nagasawa

  DOI：10.1021/jo802611t

  日期：2009.3.20

  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.