HCl*NH2-γ-OBn | 1292321-10-8

• 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: HCl*NH2-γ-OBn
• 英文别名: benzotriazol-1-yl (2S)-2-[(1S,2S)-2-[[2-[1-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]cyclohexyl]acetyl]amino]cyclohexyl]butanoate
• CAS: 1292321-10-8
• 化学式: C₃₀H₄₅N₅O₅
• 分子量: 555.718
• InChiKey: IYMMVLOVYWWMLX-VABKMULXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  40
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  124
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (S,S,S)-hydrochloride*NH2-γ-(Et)ACHA-OBn 在 (S,S,S)-hydrochloride*NH2-γ-(Et)ACHA-OBn 、 palladium 10% on activated carbon 、 氢气 、 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 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 HCl*NH2-γ-OBn
  参考文献：
  名称：

  γ-肽 14-螺旋的特征结构参数：亚基预组织的重要性

  摘要：

  全部结束：一组由加巴喷丁和 2 到 6 个预先组织的 γ-氨基酸残基构建的同源肽的晶体学数据（参见最长肽的晶体结构）允许推导 γ-肽 14-螺旋的特征参数并建立指导方针用于表征 14 螺旋折叠。结果表明，γ-残基的取代模式对 14 螺旋折叠的倾向有深远的影响。

  DOI：

  10.1002/anie.201101301

文献信息

• [EN] GAMMA AMINO ACID BUILDING BLOCKS<br/>[FR] ÉLÉMENTS CONSTITUTIFS DE GAMMA-AMINOACIDES
  申请人：WISCONSIN ALUMNI RES FOUND

  公开号：WO2011047190A1

  公开（公告）日：2011-04-21

  The invention provides compounds and methods, for example, to carry out organocatalytic Michael additions of aldehydes to cyclically constrained nitroethylene compounds catalyzed by a pro line derivative to provide cyclically constrained α-substituted-γ-nitro-aldehydes. The reaction can be rendered enantioselective when a chiral pyrrolidine catalyst is used, allowing for Michael adducts in nearly optically pure form (e.g., 96 to >99% e.e.). The Michael adducts can bear a single substituent or dual substituents adjacent to the carbonyl. The Michael adducts can be efficiently converted to cyclically constrained protected γ- amino acid residues, which are essential for systematic conformational studies of γ-peptide foldamers. New methods are also provided to prepare other γ-amino acids and peptides. These new building blocks can be used to prepare foldamers, such as α/γ-peptide foldamers, that adopt specific helical conformations in solution and in the solid state.

  该发明提供了化合物和方法，例如，用于催化贝氏碱衍生物对环状约束硝基乙烯化合物进行醛的有机催化Michael加成，从而提供环状约束的α-取代-γ-硝基醛。当使用手性吡咯烷催化剂时，反应可以实现对映选择性，从而以几乎光学纯形式（例如，96%至>99% e.e.）获得Michael加合物。Michael加合物可以在羰基相邻处携带单取代基或双取代基。Michael加合物可以高效转化为环状约束的保护γ-氨基酸残基，这对于γ-肽折叠体系的系统构象研究至关重要。还提供了制备其他γ-氨基酸和肽的新方法。这些新的构建模块可用于制备折叠体，例如α/γ-肽折叠体，在溶液中和固态中采用特定螺旋构象。
• GAMMA AMINO ACID BUILDING BLOCKS
  申请人：Gellman Samuel Helmer

  公开号：US20110118440A1

  公开（公告）日：2011-05-19

  The invention provides compounds and methods, for example, to carry out organocatalytic Michael additions of aldehydes to cyclically constrained nitroethylene compounds catalyzed by a proline derivative to provide cyclically constrained α-substituted-γ-nitro-aldehydes. The reaction can be rendered enantioselective when a chiral pyrrolidine catalyst is used, allowing for Michael adducts in nearly optically pure form (e.g., 96 to >99% e.e.). The Michael adducts can bear a single substituent or dual substituents adjacent to the carbonyl. The Michael adducts can be efficiently converted to cyclically constrained protected γ-amino acid residues, which are essential for systematic conformational studies of γ-peptide foldamers. New methods are also provided to prepare other γ-amino acids and peptides. These new building blocks can be used to prepare foldamers, such as α/γ-peptide foldamers, that adopt specific helical conformations in solution and in the solid state.
• US9382291B2
  申请人：——

  公开号：US9382291B2

  公开（公告）日：2016-07-05
• US9796660B2
  申请人：——

  公开号：US9796660B2

  公开（公告）日：2017-10-24
• Characteristic Structural Parameters for the γ-Peptide 14-Helix: Importance of Subunit Preorganization
  作者：Li Guo、Weicheng Zhang、Andrew G. Reidenbach、Michael W. Giuliano、Ilia A. Guzei、Lara C. Spencer、Samuel H. Gellman

  DOI：10.1002/anie.201101301

  日期：2011.6.20

  All wound up: Crystallographic data for a set of homologous peptides constructed from gabapentin and two to six preorganized γ‐amino acid residues (see crystal structure of the longest peptide) allow derivation of characteristic parameters for the γ‐peptide 14‐helix and establish guidelines for characterizing 14‐helical folding. The results suggest that the substitution pattern of a γ‐residue has a

  全部结束：一组由加巴喷丁和 2 到 6 个预先组织的 γ-氨基酸残基构建的同源肽的晶体学数据（参见最长肽的晶体结构）允许推导 γ-肽 14-螺旋的特征参数并建立指导方针用于表征 14 螺旋折叠。结果表明，γ-残基的取代模式对 14 螺旋折叠的倾向有深远的影响。