benzyl (2S)-2-methyl-2-[[(2S)-1-(methylamino)-1-oxopropan-2-yl]carbamoyl]azetidine-1-carboxylate | 942203-07-8

• 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: benzyl (2S)-2-methyl-2-[[(2S)-1-(methylamino)-1-oxopropan-2-yl]carbamoyl]azetidine-1-carboxylate
• CAS: 942203-07-8
• 化学式: C₁₇H₂₃N₃O₄
• 分子量: 333.387
• InChiKey: YFXBDSLBRGEIOH-SJCJKPOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  87.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl (2S)-2-methyl-2-[[(2S)-1-(methylamino)-1-oxopropan-2-yl]carbamoyl]azetidine-1-carboxylate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、103.42 kPa 条件下， 反应 1.0h， 生成 (2S)-2-methyl-N-[(2S)-1-(methylamino)-1-oxopropan-2-yl]azetidine-2-carboxamide
  参考文献：
  名称：

  Azetidine-Derived Amino Acids versus Proline Derivatives. Alternative Trends in Reverse Turn Induction

  摘要：

  [Graphics]The influence of 2-alkyl-2-carboxyazetidines (Aze) on the 3D structure of model tetrapeptides (RCO)-C-2-2-R(1)Aze-L-Ala-NHMe has been analyzed by molecular modeling, H-1 NMR, and FT-IR studies. The conformational constraints introduced by the four-membered ring resulted in an effective way to stabilize gamma-turn-like conformations in these short peptides. The conformational preferences of these Aze-containing peptides have been compared to those of the corresponding peptide analogues containing Pro or a-MePro in the place of 2-alkyl-Aze residue. In the model studied, both Pro and Aze derivatives are able to induce reverse turns, but the nature of the turn is different as a function of the ring size. While the five-membered ring of Pro tends to induce beta-turns, as previously suggested by different authors, the four-membered ring of Aze residues forces the peptide to preferentially adopt gamma-turn conformations. In both cases, the presence of an alkyl group at the alpha-position of Pro or the azetidine-2-carboxylate ring enhances significantly the turn-inducing ability. These results might open the opportunity of using 2-alkyl-Aze residues as versatile tools in defining the role of gamma-turn structures within the bioactive conformation of selected peptides, and represent an alternative to Pro derivatives as turn inducers.

  DOI：

  10.1021/jo701746w
• 作为产物：
  描述：

  1-benzyl 2-((1R,2S,4S)-1-((N,N-dicyclohexylsulfamoyl)methyl)-7,7-dimethylbicyclo[2.2.1]heptan-2-yl) (S)-2-methylazetidine-1,2-dicarboxylate 在 sodium hydroxide 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 作用下， 生成 benzyl (2S)-2-methyl-2-[[(2S)-1-(methylamino)-1-oxopropan-2-yl]carbamoyl]azetidine-1-carboxylate
  参考文献：
  名称：

  2-Alkyl-2-carboxy-azetidines as scaffolds for the induction of γ-turns

  摘要：

  To investigate the ability of 2-alkyl-2-carboxy-azetidines (Azx) to induce reverse turns when incorporated into peptides, RCO-Azx-L-A1a-NHMe dipeptide derivatives were selected as simplified tetrapeptide models, in which the azetidine residue is incorporated at the i + 1 position. Molecular modelling, H-1 NMR and FTIR studies showed the high tendency of the model tetrapeptides to adopt gamma-turn conformations, indicating that these azetidine-containing amino acids could serve as general gamma-turn promoters. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.03.126

文献信息

• Azetidine-Derived Amino Acids versus Proline Derivatives. Alternative Trends in Reverse Turn Induction
  作者：José Luis Baeza、Guillermo Gerona-Navarro、Jesús Pérez de Vega、M. Teresa García-López、Rosario González-Muñiz、Mercedes Martín-Martínez

  DOI：10.1021/jo701746w

  日期：2008.3.1

  [Graphics]The influence of 2-alkyl-2-carboxyazetidines (Aze) on the 3D structure of model tetrapeptides (RCO)-C-2-2-R(1)Aze-L-Ala-NHMe has been analyzed by molecular modeling, H-1 NMR, and FT-IR studies. The conformational constraints introduced by the four-membered ring resulted in an effective way to stabilize gamma-turn-like conformations in these short peptides. The conformational preferences of these Aze-containing peptides have been compared to those of the corresponding peptide analogues containing Pro or a-MePro in the place of 2-alkyl-Aze residue. In the model studied, both Pro and Aze derivatives are able to induce reverse turns, but the nature of the turn is different as a function of the ring size. While the five-membered ring of Pro tends to induce beta-turns, as previously suggested by different authors, the four-membered ring of Aze residues forces the peptide to preferentially adopt gamma-turn conformations. In both cases, the presence of an alkyl group at the alpha-position of Pro or the azetidine-2-carboxylate ring enhances significantly the turn-inducing ability. These results might open the opportunity of using 2-alkyl-Aze residues as versatile tools in defining the role of gamma-turn structures within the bioactive conformation of selected peptides, and represent an alternative to Pro derivatives as turn inducers.
• 2-Alkyl-2-carboxy-azetidines as scaffolds for the induction of γ-turns
  作者：José Luis Baeza、Guillermo Gerona-Navarro、Ma Jesús Pérez de Vega、Ma Teresa García-López、Rosario González-Muñiz、Mercedes Martín-Martínez

  DOI：10.1016/j.tetlet.2007.03.126

  日期：2007.5

  To investigate the ability of 2-alkyl-2-carboxy-azetidines (Azx) to induce reverse turns when incorporated into peptides, RCO-Azx-L-A1a-NHMe dipeptide derivatives were selected as simplified tetrapeptide models, in which the azetidine residue is incorporated at the i + 1 position. Molecular modelling, H-1 NMR and FTIR studies showed the high tendency of the model tetrapeptides to adopt gamma-turn conformations, indicating that these azetidine-containing amino acids could serve as general gamma-turn promoters. (c) 2007 Elsevier Ltd. All rights reserved.