Boc-(Et)ACHA-OH | 1194837-24-5

• 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: Boc-(Et)ACHA-OH
• 英文别名: (2R)-2-[(1R,2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]cyclohexyl]butanoic acid
• CAS: 1194837-24-5
• 化学式: C₁₅H₂₇NO₄
• 分子量: 285.384
• InChiKey: DFUXPEGDTMBEHD-IJLUTSLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Boc-(Et)ACHA-OH 在 盐酸 、 4-二甲氨基吡啶 、 caesium carbonate 、 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 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 benzyl (2R)-2-[(1R,2R)-2-[[(2R)-2-[(1R,2R)-2-[[2-[1-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]cyclohexyl]acetyl]amino]cyclohexyl]butanoyl]amino]cyclohexyl]butanoate
  参考文献：
  名称：

  [EN] GAMMA AMINO ACID BUILDING BLOCKS
  [FR] ÉLÉMENTS CONSTITUTIFS DE GAMMA-AMINOACIDES

  摘要：

  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。

  公开号：

  WO2011047190A1

文献信息

• Stereospecific Synthesis of Conformationally Constrained γ-Amino Acids: New Foldamer Building Blocks That Support Helical Secondary Structure
  作者：Li Guo、Yonggui Chi、Aaron M. Almeida、Ilia A. Guzei、Brian K. Parker、Samuel H. Gellman

  DOI：10.1021/ja907233q

  日期：2009.11.11

  A highly stereoselective synthesis of novel cyclically constrained gamma-amino acid residues is presented. The key step involves organocatalytic Michael addition of an aldehyde to 1-nitrocyclohexene. After aldehyde reduction, this approach provides optically active beta-substituted delta-nitro alcohols (96-99% ee), which can be converted to gamma-amino acid residues with a variety of substituents at

  提出了新型环状受限γ-氨基酸残基的高度立体选择性合成。关键步骤涉及醛与 1-硝基环己烯的有机催化迈克尔加成。醛还原后，该方法提供光学活性的β-取代的δ-硝基醇(96-99% ee)，其可以转化为在α位具有多种取代基的γ-氨基酸残基。我们使用这些新的构建模块来制备α/γ-肽折叠体，其在溶液和固态下采用特定的螺旋构象。
• Helix Formation in Preorganized β/γ-Peptide Foldamers: Hydrogen-Bond Analogy to the α-Helix without α-Amino Acid Residues
  作者：Li Guo、Aaron M. Almeida、Weicheng Zhang、Andrew G. Reidenbach、Soo Hyuk Choi、Ilia A. Guzei、Samuel H. Gellman

  DOI：10.1021/ja103233a

  日期：2010.6.16

  We report the first high-resolution structural data for the beta/gamma-peptide 13-helix (i,i+3 C=O center dot center dot center dot H-N H-bonds), a secondary structure that is formed by oligomers with a 1:1 alternation of beta- and gamma-amino acid residues. Our characterization includes both crystallophaphic and 2D NMR data. Previous studies suggested that beta/gamma-peptides constructed from conformationally flexible residues adopt a different helical secondary structure in solution. Our design features preorganized beta- and gamma-residues, which strongly promote 13-helical folding by the 1:1 beta/gamma backbone.
• 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.
• US8664356B2
  申请人：——

  公开号：US8664356B2

  公开（公告）日：2014-03-04
• US9382291B2
  申请人：——

  公开号：US9382291B2

  公开（公告）日：2016-07-05