benzyl 2-[[(2S)-1-methoxy-1-oxopropan-2-yl]carbamoyl]-2-methylazetidine-1-carboxylate | 1013038-62-4

• 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 2-[[(2S)-1-methoxy-1-oxopropan-2-yl]carbamoyl]-2-methylazetidine-1-carboxylate
• CAS: 1013038-62-4
• 化学式: C₁₇H₂₂N₂O₅
• 分子量: 334.372
• InChiKey: NYSKSTSWLCDTFQ-WHUIICBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  84.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzyl 2-[[(2S)-1-methoxy-1-oxopropan-2-yl]carbamoyl]-2-methylazetidine-1-carboxylate 、 甲胺 以 乙醇 为溶剂， 以58%的产率得到1-N,2-dimethyl-2-N-[(2S)-1-(methylamino)-1-oxopropan-2-yl]azetidine-1,2-dicarboxamide
  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-[(benzyloxy)carbonyl]-2-methylazetidine-2-carboxylic acid 、 L-丙氨酸甲酯盐酸盐 在 TEA 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以89%的产率得到benzyl 2-[[(2S)-1-methoxy-1-oxopropan-2-yl]carbamoyl]-2-methylazetidine-1-carboxylate
  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

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.