benzyl (1R,2R)-2-[[[(2R)-2-[[(1R,2R)-2-[[[(2R)-2-[[(1R,2R)-2-[[[(2R)-2-[[(1R,2R)-2-[[[(2R)-2-[[(1R,2R)-2-[[[(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]methyl]cyclopentanecarbonyl]amino]propanoyl]amino]methyl]cyclopentanecarbonyl]amino]propanoyl]amino]methyl]cyclopentanecarbonyl]amino]-3-phenylpropanoyl]amino]methyl]cyclopentanecarbonyl]amino]-3-phenylpropanoyl]amino]methyl]cyclopentane-1-carboxylate | 1509907-85-0

• 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: benzyl (1R,2R)-2-[[[(2R)-2-[[(1R,2R)-2-[[[(2R)-2-[[(1R,2R)-2-[[[(2R)-2-[[(1R,2R)-2-[[[(2R)-2-[[(1R,2R)-2-[[[(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]methyl]cyclopentanecarbonyl]amino]propanoyl]amino]methyl]cyclopentanecarbonyl]amino]propanoyl]amino]methyl]cyclopentanecarbonyl]amino]-3-phenylpropanoyl]amino]methyl]cyclopentanecarbonyl]amino]-3-phenylpropanoyl]amino]methyl]cyclopentane-1-carboxylate
• CAS: 1509907-85-0
• 化学式: C₇₄H₁₀₄N₁₀O₁₃
• 分子量: 1341.7
• InChiKey: CLVWRONFZZSAIN-HTAKLNGTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  97
• 可旋转键数：
  34
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  327
• 氢给体数：
  10
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  、 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 2-肟氰乙酸乙酯 作用下， 以 N-甲基吡咯烷酮 、 二甲基亚砜 为溶剂， 反应 120.0h， 以77%的产率得到benzyl (1R,2R)-2-[[[(2R)-2-[[(1R,2R)-2-[[[(2R)-2-[[(1R,2R)-2-[[[(2R)-2-[[(1R,2R)-2-[[[(2R)-2-[[(1R,2R)-2-[[[(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]methyl]cyclopentanecarbonyl]amino]propanoyl]amino]methyl]cyclopentanecarbonyl]amino]propanoyl]amino]methyl]cyclopentanecarbonyl]amino]-3-phenylpropanoyl]amino]methyl]cyclopentanecarbonyl]amino]-3-phenylpropanoyl]amino]methyl]cyclopentane-1-carboxylate
  参考文献：
  名称：

  Evaluation of a Cyclopentane-Based γ-Amino Acid for the Ability to Promote α/γ-Peptide Secondary Structure

  摘要：

  We report the asymmetric synthesis of the gamma-amino acid (1R,2R)-2-aminomethyl-1-cyclopentane carboxylic acid (AMCP) and an evaluation of this residue's potential to promote secondary structure in alpha/gamma-peptides. Simulated annealing calculations using NMR-derived distance restraints obtained for alpha/gamma-peptides in chloroform reveal that AMCP-containing oligomers are conformationally flexible. However, additional evidence suggests that an internally hydrogen-bonded helical conformation is partially populated in solution. From these data, we propose characteristic NOE patterns for the formation of the alpha/gamma-peptide 12/10-helix and discuss the apparent conformational frustration of AMCP-containing oligomers.

  DOI：

  10.1021/jo401501g