methyl (2R)-2-benzyl-1-[(2S)-2-(phenylmethoxycarbonylamino)propanoyl]azetidine-2-carboxylate | 1192501-26-0

• 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: methyl (2R)-2-benzyl-1-[(2S)-2-(phenylmethoxycarbonylamino)propanoyl]azetidine-2-carboxylate
• CAS: 1192501-26-0
• 化学式: C₂₃H₂₆N₂O₅
• 分子量: 410.47
• InChiKey: AROQCGFQMRMROE-SBUREZEXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  84.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  苄氧羰基-L-丙氨酸 、 2-benzyl-2-methoxycarbonylazetidine 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以54%的产率得到methyl (2S)-2-benzyl-1-[(2S)-2-(phenylmethoxycarbonylamino)propanoyl]azetidine-2-carboxylate
  参考文献：
  名称：

  Further Evidence for 2-Alkyl-2-carboxyazetidines as γ-Turn Inducers

  摘要：

  Reverse turns, it common motif in proteins and peptides, have attracted attention due to their relevance in it Wide variety of biological processes. In in attempt to artificially imitate and stabilize these turns in short peptides, we have developed versatile synthetic methodologies for the preparation of 2-alkyl-2-carboxyazetidines, and incorporated them into the i + 1 position of model tetrapeptides, where they have shown it tendency to induce gamma-turns However, to ascertain the general utility of these restricted amino acids its gamma-type reverse turn inducers, it was then required to study the conformational preferences when located at other positions. To this end, model tetrapeptides R-CO-Ala-Xaa-NHMe, containing differently Substituted azetidine moieties (Xaa = Aze, 2-MeAze, 2-BnAze) at the i + 2 position, were synthesized and Subjected to it thorough conformational analysis. The theoretical and experimental results obtained, including the X-ray diffraction structure of a dipeptide derivative containing this skeleton, provide evidence that the 2-alkyl-2-carboxyazetidine scaffold is able to efficiently induce gamma-turns when incorporated into these short peptides, irrespective of their localization in the peptide chain.

  DOI：

  10.1021/jo901712x

文献信息

• Further Evidence for 2-Alkyl-2-carboxyazetidines as γ-Turn Inducers
  作者：José Luis Baeza、Guillermo Gerona-Navarro、Kevin Thompson、M. Jesús Pérez de Vega、Lourdes Infantes、M. Teresa García-López、Rosario González-Muñiz、Mercedes Martín-Martínez

  DOI：10.1021/jo901712x

  日期：2009.11.6

  Reverse turns, it common motif in proteins and peptides, have attracted attention due to their relevance in it Wide variety of biological processes. In in attempt to artificially imitate and stabilize these turns in short peptides, we have developed versatile synthetic methodologies for the preparation of 2-alkyl-2-carboxyazetidines, and incorporated them into the i + 1 position of model tetrapeptides, where they have shown it tendency to induce gamma-turns However, to ascertain the general utility of these restricted amino acids its gamma-type reverse turn inducers, it was then required to study the conformational preferences when located at other positions. To this end, model tetrapeptides R-CO-Ala-Xaa-NHMe, containing differently Substituted azetidine moieties (Xaa = Aze, 2-MeAze, 2-BnAze) at the i + 2 position, were synthesized and Subjected to it thorough conformational analysis. The theoretical and experimental results obtained, including the X-ray diffraction structure of a dipeptide derivative containing this skeleton, provide evidence that the 2-alkyl-2-carboxyazetidine scaffold is able to efficiently induce gamma-turns when incorporated into these short peptides, irrespective of their localization in the peptide chain.