Boc-(R,R)-trans-2-aminocyclohexanecarboxylic acid benzyl ester | 185153-71-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Boc-(R,R)-trans-2-aminocyclohexanecarboxylic acid benzyl ester
• 英文别名: benzyl (1R,2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]cyclohexane-1-carboxylate
• CAS: 185153-71-3
• 化学式: C₁₉H₂₇NO₄
• 分子量: 333.428
• InChiKey: HCWMUULFUPYFTM-HZPDHXFCSA-N

物化性质

• 沸点：
  451.9±34.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Boc-(R,R)-trans-2-aminocyclohexanecarboxylic acid benzyl ester 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 生成 (R,R)-trans-2-aminocyclohexanecarboxylic acid benzyl ester
  参考文献：
  名称：

  Synthesis and Characterization of trans-2-Aminocyclohexanecarboxylic Acid Oligomers:  An Unnatural Helical Secondary Structure and Implications for β-Peptide Tertiary Structure

  摘要：

  The preperation, crystal structures, and circular dichroism(CD)spectra of two oligomers of optically active trans-2-aminocyclohexanecarboxylic acid are reported. In the solid state, both the tetramer and the hexamer of this beta-amino acid display a helical conformation that involves 14-membered-ring hydrogen bonds between a carbonyl oxygen and the amide proton of the second residue toward the N-terminus. (For comparison, the familiar cc-helix observed in conventional peptides is associated with a 13-membered-ring hydrogen, bond between a carbonyl oxygen and the amide proton of the fourth residue toward the C-terminus.) These. :crystallographic data, along with CD data obtained in methanol, suggest that the 14-helix constitutes a stable secondary structure for beta-amino acid oligomers ("beta-peptides"). In addition, the cryst al packing pattern observed for the hexamer offers a blueprint for the design of beta-peptides that might adopt a helical bundle tertiary structure.

  DOI：

  10.1021/ja990748l
• 作为产物：
  描述：

  (+/-)-N-benzoyl-trans-2-aminocyclohexane-carboxylic acid 在 盐酸 、 1,4-diazabicycloundecene 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 苯 为溶剂， 反应 59.0h， 生成 Boc-(R,R)-trans-2-aminocyclohexanecarboxylic acid benzyl ester
  参考文献：
  名称：

  Synthesis and Characterization of trans-2-Aminocyclohexanecarboxylic Acid Oligomers:  An Unnatural Helical Secondary Structure and Implications for β-Peptide Tertiary Structure

  摘要：

  The preperation, crystal structures, and circular dichroism(CD)spectra of two oligomers of optically active trans-2-aminocyclohexanecarboxylic acid are reported. In the solid state, both the tetramer and the hexamer of this beta-amino acid display a helical conformation that involves 14-membered-ring hydrogen bonds between a carbonyl oxygen and the amide proton of the second residue toward the N-terminus. (For comparison, the familiar cc-helix observed in conventional peptides is associated with a 13-membered-ring hydrogen, bond between a carbonyl oxygen and the amide proton of the fourth residue toward the C-terminus.) These. :crystallographic data, along with CD data obtained in methanol, suggest that the 14-helix constitutes a stable secondary structure for beta-amino acid oligomers ("beta-peptides"). In addition, the cryst al packing pattern observed for the hexamer offers a blueprint for the design of beta-peptides that might adopt a helical bundle tertiary structure.

  DOI：

  10.1021/ja990748l

文献信息

• HETEROGENEOUS FOLDAMERS CONTAINING alpha, beta, and/or gamma-AMINO ACIDS
  申请人：Gellman Samuel H.

  公开号：US20120021530A1

  公开（公告）日：2012-01-26

  Disclosed are isolated, unnatural polypeptides containing cyclically-constrained β-amino acid residues and cyclically-constrained γ-amino acid residues. The compounds are unnatural and because they contain rotationally constrained residues that are not amenable to enzymatic degradation, the compounds are useful to probe protein-protein and other large molecule interactions.

  本发明涉及一种孤立的、非天然的多肽，其中包含有环限制的β-氨基酸残基和环限制的γ-氨基酸残基。这些化合物是非天然的，因为它们包含有旋转限制的残基，不易于酶降解，因此这些化合物可用于探究蛋白质-蛋白质和其他大分子相互作用。
• Heterogeneous foldamers containing α, β, and/or γ-amino acids
  申请人：Gellman Samuel H.

  公开号：US10322998B2

  公开（公告）日：2019-06-18

  Disclosed are isolated, unnatural polypeptides containing cyclically-constrained β-amino acid residues and cyclically-constrained γ-amino acid residues. The compounds are unnatural and because they contain rotationally constrained residues that are not amenable to enzymatic degradation, the compounds are useful to probe protein-protein and other large molecule interactions.

  本发明公开了分离的非天然多肽，这些多肽含有旋转受限的 β 氨基酸残基和旋转受限的 γ 氨基酸残基。这些化合物是非天然的，由于它们含有旋转受限的残基，不易被酶降解，因此这些化合物可用于探测蛋白质-蛋白质和其他大分子之间的相互作用。
• US7858737B2
  申请人：——

  公开号：US7858737B2

  公开（公告）日：2010-12-28
• Synthesis and Characterization of <i>trans</i>-2-Aminocyclohexanecarboxylic Acid Oligomers:  An Unnatural Helical Secondary Structure and Implications for β-Peptide Tertiary Structure
  作者：Daniel H. Appella、Laurie A. Christianson、Isabella L. Karle、Douglas R. Powell、Samuel H. Gellman

  DOI：10.1021/ja990748l

  日期：1999.7.1

  The preperation, crystal structures, and circular dichroism(CD)spectra of two oligomers of optically active trans-2-aminocyclohexanecarboxylic acid are reported. In the solid state, both the tetramer and the hexamer of this beta-amino acid display a helical conformation that involves 14-membered-ring hydrogen bonds between a carbonyl oxygen and the amide proton of the second residue toward the N-terminus. (For comparison, the familiar cc-helix observed in conventional peptides is associated with a 13-membered-ring hydrogen, bond between a carbonyl oxygen and the amide proton of the fourth residue toward the C-terminus.) These. :crystallographic data, along with CD data obtained in methanol, suggest that the 14-helix constitutes a stable secondary structure for beta-amino acid oligomers ("beta-peptides"). In addition, the cryst al packing pattern observed for the hexamer offers a blueprint for the design of beta-peptides that might adopt a helical bundle tertiary structure.