(S)-N-((R)-1-amino-1-oxo-3-(phenylselanyl)propan-2-yl)-1-(((R)-2-amino-3-(phenylselanyl)propanoyl)-L-alanyl)pyrrolidine-2-carboxamide 2,2,2-trifluoroacetate | 1607794-62-6

• 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: (S)-N-((R)-1-amino-1-oxo-3-(phenylselanyl)propan-2-yl)-1-(((R)-2-amino-3-(phenylselanyl)propanoyl)-L-alanyl)pyrrolidine-2-carboxamide 2,2,2-trifluoroacetate
• CAS: 1607794-62-6
• 化学式: C₂HF₃O₂*C₂₆H₃₃N₅O₄Se₂
• 分子量: 751.523
• InChiKey: LXFJGWGCBYWRSU-MXSRVJTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.69
• 重原子数：
  44.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  184.92
• 氢给体数：
  5.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  、 (S)-N-((R)-1-amino-1-oxo-3-(phenylselanyl)propan-2-yl)-1-(((R)-2-amino-3-(phenylselanyl)propanoyl)-L-alanyl)pyrrolidine-2-carboxamide 2,2,2-trifluoroacetate 在 N-羟基-7-氮杂苯并三氮唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 以45 mg的产率得到
  参考文献：
  名称：

  Dissecting the Structure of Thiopeptides: Assessment of Thiazoline and Tail Moieties of Baringolin and Antibacterial Activity Optimization

  摘要：

  Several analogues of baringolin (1) were prepared to evaluate the role of its characteristic thiazoline ring and pentapeptidic tail with the aim of defining structure activity relationships for these moieties. The thiazoline ring appeared as a crucial moiety to maintain a broad scope of activities against different Gram-positive bacteria. Further modifications were performed to simplify the structure of the natural product and assess the role of its tail, resulting in an enhanced in vitro performance. Analogue 25, with the thiazole-containing macrocycle and a 4-aminocyclohexane-1-carboxylic acid moiety in place of the pentapeptidic tail, was identified as a much more potent analogue, capable of overcoming the absence of the thiazoline ring and performing extraordinarily well against all strains tested.,This is the first library of thiopeptide analogues produced by chemical synthesis alone, which demonstrates the robustness and convenience of the synthetic strategy used.

  DOI：

  10.1021/jm500062g
• 作为产物：
  描述：

  Fmoc-L-丙氨酸 、 Fmoc-L-脯氨酸 、 三氟乙酸 、 Fmoc-Sec(Ph)-OH 在 2-肟氰乙酸乙酯 、 N,N'-二异丙基碳二亚胺 、 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.7h， 以100%的产率得到(S)-N-((R)-1-amino-1-oxo-3-(phenylselanyl)propan-2-yl)-1-(((R)-2-amino-3-(phenylselanyl)propanoyl)-L-alanyl)pyrrolidine-2-carboxamide 2,2,2-trifluoroacetate
  参考文献：
  名称：

  Dissecting the Structure of Thiopeptides: Assessment of Thiazoline and Tail Moieties of Baringolin and Antibacterial Activity Optimization

  摘要：

  Several analogues of baringolin (1) were prepared to evaluate the role of its characteristic thiazoline ring and pentapeptidic tail with the aim of defining structure activity relationships for these moieties. The thiazoline ring appeared as a crucial moiety to maintain a broad scope of activities against different Gram-positive bacteria. Further modifications were performed to simplify the structure of the natural product and assess the role of its tail, resulting in an enhanced in vitro performance. Analogue 25, with the thiazole-containing macrocycle and a 4-aminocyclohexane-1-carboxylic acid moiety in place of the pentapeptidic tail, was identified as a much more potent analogue, capable of overcoming the absence of the thiazoline ring and performing extraordinarily well against all strains tested.,This is the first library of thiopeptide analogues produced by chemical synthesis alone, which demonstrates the robustness and convenience of the synthetic strategy used.

  DOI：

  10.1021/jm500062g