benzyl (S)-1-(2-(tert-butoxycarbonylamino)benzoyl)pyrrolidine-2-carboxylate | 1094297-20-7

• 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 (S)-1-(2-(tert-butoxycarbonylamino)benzoyl)pyrrolidine-2-carboxylate
• 英文别名: benzyl 1-(2-(tert-butoxycarbonylamino)benzoyl)pyrrolidine-2-carboxylate；benzyl (2S)-1-[2-[(2-methylpropan-2-yl)oxycarbonylamino]benzoyl]pyrrolidine-2-carboxylate
• CAS: 1094297-20-7
• 化学式: C₂₄H₂₈N₂O₅
• 分子量: 424.497
• InChiKey: UFZWINKETKHYTK-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 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 (S)-1-(2-(tert-butoxycarbonylamino)benzoyl)pyrrolidine-2-carboxylate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 1-(2-(tert-butoxycarbonylamino)benzoyl)pyrrolidine-2-carboxylic acid
  参考文献：
  名称：

  Sequence-Specific Unusual (1→2)-Type Helical Turns in α/β-Hybrid Peptides

  摘要：

  This article describes novel conformationally ordered (alpha/beta-hybrid peptides consisting of repeating L-proline-anthranilic acid building blocks. These oligomers adopt a compact, right-handed helical architecture determined by the intrinsic conformational preferences of the individual amino acid residues. The striking feature of these oligomers is their ability to display an unusual periodic pseudo beta-turn network of nine-membered hydrogen-bonded rings formed in the forward direction of the sequence by 1-->2 amino acid interactions both in solid-state and in solution. Conformational investigations of several of these oligomers by single-crystal X-ray diffraction, solution-state NMR, and ab initio MO theory suggest that the characteristic steric and dihedral angle restraints exerted by proline are essential for stabilizing the unusual pseudo beta-turn network found in these oligomers. Replacing proline by the conformationally flexible analogue alanine (Ala) or by the conformationally more constrained alpha-amino isobutyric acid (Aib) had an adverse effect on the stabilization of this structural architecture. These findings increase the potential to design novel secondary structure elements profiting from the steric and dihedral angle constraints of the amino acid constituents and help to augment the conformational space available for synthetic oligomer design with diverse backbone structures.

  DOI：

  10.1021/ja804297f
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 15.0h， 生成 benzyl (S)-1-(2-(tert-butoxycarbonylamino)benzoyl)pyrrolidine-2-carboxylate
  参考文献：
  名称：

  Ester vs. amide on folding: a case study with a 2-residue synthetic peptide

  摘要：

  尽管在作为氢键受体方面与酰胺相比被认为质量较差，酯类却常常出现在肽链和合成寡聚体（折叠体）的C末端，这很可能是因为它们在使用保护性肽耦合反应、在C末端部署氨基酸酯时易于合成。当末端的氢键相互作用偏离规则时，肽链往往会“散开”。然而，C末端酯对肽链末端散开的单独贡献常常被忽视，特别是因为大型肽链存在多种竞争效应。在此，我们描述了一个引人注目的案例，比较了C末端酯与酰胺羰基在促进肽折叠中作为氢键受体的个别贡献。我们使用了一个简单的两残基肽折叠作为测试案例，证明酰胺羰基在促进肽折叠、防止末端散开方面远胜于酯羰基。这一发现将对理解稳定/不稳定非共价相互作用在肽折叠中个别贡献的基本理解产生影响。

  DOI：

  10.1039/c3ob41967c