(2S,3S)-2-(tert-butoxycarbonylamino)-3-fluoro-3-phenylpropanoic acid | 1132645-38-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,3S)-2-(tert-butoxycarbonylamino)-3-fluoro-3-phenylpropanoic acid
• 英文别名: (3S)-N-Boc-3-fluoro-L-Phe；Rel-(2R,3R)-2-((tert-butoxycarbonyl)amino)-3-fluoro-3-phenylpropanoic acid；(2S,3S)-3-fluoro-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoic acid
• CAS: 1132645-38-5
• 化学式: C₁₄H₁₈FNO₄
• 分子量: 283.3
• InChiKey: WBMMLSLUBCWSFY-WDEREUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3S)-2-(tert-butoxycarbonylamino)-3-fluoro-3-phenylpropanoic acid 在 吡啶 、 三聚氟氰 作用下， 以 二氯甲烷 为溶剂， 生成
  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：

  在 sodium hypochlorite 、 2,2,6,6-四甲基哌啶氧化物 、 四丁基溴化铵 、 碳酸氢钠 、 盐酸 、 水 作用下， 以 水 、 乙酸乙酯 为溶剂， 以94%的产率得到(2S,3S)-2-(tert-butoxycarbonylamino)-3-fluoro-3-phenylpropanoic acid
  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.