(S)-1-{(2S,3S)-2-Phenylselanyl-3-[(S)-2-(2,2,2-trifluoro-acetylamino)-propionylamino]-butyryl}-pyrrolidine-2-carboxylic acid ((S)-1-dimethylcarbamoyl-2-methyl-propyl)-amide | 190598-44-8

• 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)-1-{(2S,3S)-2-Phenylselanyl-3-[(S)-2-(2,2,2-trifluoro-acetylamino)-propionylamino]-butyryl}-pyrrolidine-2-carboxylic acid ((S)-1-dimethylcarbamoyl-2-methyl-propyl)-amide
• 英文别名: (2S)-N-[(2S)-1-(dimethylamino)-3-methyl-1-oxobutan-2-yl]-1-[(2S,3S)-2-phenylselanyl-3-[[(2S)-2-[(2,2,2-trifluoroacetyl)amino]propanoyl]amino]butanoyl]pyrrolidine-2-carboxamide
• CAS: 190598-44-8
• 化学式: C₂₇H₃₈F₃N₅O₅Se
• 分子量: 648.584
• InChiKey: KCDADMYXCPGVCP-XYYCENQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  41
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  128
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  烯丙基三丁基锡 、 (S)-1-{(2S,3S)-2-Phenylselanyl-3-[(S)-2-(2,2,2-trifluoro-acetylamino)-propionylamino]-butyryl}-pyrrolidine-2-carboxylic acid ((S)-1-dimethylcarbamoyl-2-methyl-propyl)-amide 在 偶氮二异丁腈 作用下， 以 二氯甲烷 为溶剂， 以58%的产率得到(S)-1-((S)-2-{(S)-1-[(S)-2-(2,2,2-Trifluoro-acetylamino)-propionylamino]-ethyl}-pent-4-enoyl)-pyrrolidine-2-carboxylic acid ((S)-1-dimethylcarbamoyl-2-methyl-propyl)-amide
  参考文献：
  名称：

  Design of a novel secondary structure scaffolding device: Induction of a reverse turn in tetrapeptides by incorporating a β-amino acid and stereocontrolled free radical α-substitution reactions in peptide motifs

  摘要：

  The incorporation of alpha-substituted beta-amino acids into a tetrapeptide motif induces a reverse turn in aprotic solvent systems as revealed by NOESY and ROESY techniques, and by CD spectra. The conformations of these compounds have been studied by molecular modeling, and further supported by performing a highly stereoselective free radical allylation reaction on an alpha-phenylselena beta-amino acid unit within the tetrapeptide. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00612-6
• 作为产物：
  描述：

  (2S,3S)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-2-phenylselanylbutanoic acid 在 盐酸 、 TEA 、 四丁基氟化铵 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 乙腈 为溶剂， 生成 (S)-1-{(2S,3S)-2-Phenylselanyl-3-[(S)-2-(2,2,2-trifluoro-acetylamino)-propionylamino]-butyryl}-pyrrolidine-2-carboxylic acid ((S)-1-dimethylcarbamoyl-2-methyl-propyl)-amide
  参考文献：
  名称：

  Design of a novel secondary structure scaffolding device: Induction of a reverse turn in tetrapeptides by incorporating a β-amino acid and stereocontrolled free radical α-substitution reactions in peptide motifs

  摘要：

  The incorporation of alpha-substituted beta-amino acids into a tetrapeptide motif induces a reverse turn in aprotic solvent systems as revealed by NOESY and ROESY techniques, and by CD spectra. The conformations of these compounds have been studied by molecular modeling, and further supported by performing a highly stereoselective free radical allylation reaction on an alpha-phenylselena beta-amino acid unit within the tetrapeptide. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00612-6