2-(trimethylsilyl)ethyl 8-amino-4-isobutoxyquinoline-2-carboxylate | 1443682-82-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-(trimethylsilyl)ethyl 8-amino-4-isobutoxyquinoline-2-carboxylate
• CAS: 1443682-82-3
• 化学式: C₁₉H₂₈N₂O₃Si
• 分子量: 360.528
• InChiKey: JINLLNVEUGHRLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.35
• 重原子数：
  25.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  74.44
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl 8-amino-4-isobutoxyquinoline-2-carboxylate 在 盐酸 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 氯仿 为溶剂， 反应 38.0h， 生成
  参考文献：
  名称：

  Folding of a Linear Array of α-Amino Acids within a Helical Aromatic Oligoamide Frame

  摘要：

  Control of the spatial organization of proteinogenic side chains is critical for the development of protein mimics with selective recognition properties toward target protein surfaces. We present a novel methodology for producing a linear array of proteinogenic residues based on the incorporation of alpha-amino acids into sequences of rigid, helically folded oligoamides of 8-amino-2-quinolinecarboxylic acid (Q). When l-leucine (L) was alternated with dimer Q(2), the resulting sequence adopted a right-handed helical conformation, as deduced in solution from the CD spectra of L-(LQ(2))(n) (n = 2, 4) and in the solid state from X-ray crystallographic analysis of (+/-)-(LQ(2))(4). Each LQ(2) segment spanned just one helix turn (pitch of 3.5 angstrom), and consequently, the four leucine side chains of (LQ(2))(4) formed a linear array. In solution, NMR analysis showed that both L-(LQ(2))(2) and L-(LQ(2))(4) exist as a mixture of two slowly equilibrating folded conformers, the proportion of which strongly varies with the solvent.

  DOI：

  10.1021/ja404656z
• 作为产物：
  描述：

  2-<(2-nitrophenyl)amino>-2-butenedioic acid dimethyl ester 在 甲醇 、 偶氮二甲酸二异丙酯 、 palladium 10% on activated carbon 、 ammonium vanadate 、 氢气 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 三苯基膦 、 potassium hydroxide 作用下， 以 四氢呋喃 、 二苯醚 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 41.75h， 生成 2-(trimethylsilyl)ethyl 8-amino-4-isobutoxyquinoline-2-carboxylate
  参考文献：
  名称：

  Folding of a Linear Array of α-Amino Acids within a Helical Aromatic Oligoamide Frame

  摘要：

  Control of the spatial organization of proteinogenic side chains is critical for the development of protein mimics with selective recognition properties toward target protein surfaces. We present a novel methodology for producing a linear array of proteinogenic residues based on the incorporation of alpha-amino acids into sequences of rigid, helically folded oligoamides of 8-amino-2-quinolinecarboxylic acid (Q). When l-leucine (L) was alternated with dimer Q(2), the resulting sequence adopted a right-handed helical conformation, as deduced in solution from the CD spectra of L-(LQ(2))(n) (n = 2, 4) and in the solid state from X-ray crystallographic analysis of (+/-)-(LQ(2))(4). Each LQ(2) segment spanned just one helix turn (pitch of 3.5 angstrom), and consequently, the four leucine side chains of (LQ(2))(4) formed a linear array. In solution, NMR analysis showed that both L-(LQ(2))(2) and L-(LQ(2))(4) exist as a mixture of two slowly equilibrating folded conformers, the proportion of which strongly varies with the solvent.

  DOI：

  10.1021/ja404656z

文献信息

• Self-Assembled Protein–Aromatic Foldamer Complexes with 2:3 and 2:2:1 Stoichiometries
  作者：Michal Jewginski、Thierry Granier、Béatrice Langlois d’Estaintot、Lucile Fischer、Cameron D. Mackereth、Ivan Huc

  DOI：10.1021/jacs.7b00184

  日期：2017.3.1

  ligand was explored and shown to produce complexes with unusual stoichiometries. Helical foldamer 2 was synthesized and bound to human carbonic anhydrase (HCA) using a nanomolar active site ligand. Crystal structures show that the hydrophobicity of 2 and interactions of its side chains lead to the formation of an HCA2-23 complex in which three helices of 2 are stacked, two of them being linked to an

  探索了使用蛋白质配体的聚集特性促进蛋白质二聚化，并显示出产生具有不寻常化学计量的复合物。合成螺旋折叠体 2 并使用纳摩尔活性位点配体与人碳酸酐酶 (HCA) 结合。晶体结构显示 2 的疏水性及其侧链的相互作用导致形成 HCA2-23 复合物，其中 2 的三个螺旋堆叠，其中两个连接到 HCA 分子。堆栈中的中间折叠体可以被替代序列 3 或 5 替换。 CD 和 NMR 的解决方案研究证实了螺旋折叠体的左旋性以及 HCA 二聚化。
• Iterative Evolution of an Abiotic Foldamer Sequence for the Recognition of Guest Molecules with Atomic Precision
  作者：Guillaume Lautrette、Barbara Wicher、Brice Kauffmann、Yann Ferrand、Ivan Huc

  DOI：10.1021/jacs.6b05913

  日期：2016.8.17

  A synthetic helical aromatic oligoamide foldamer receptor with high affinity and selectivity for tartaric acid was subjected to a structure-based evolution of its sequence via mutations, additions, and deletions of monomers to produce a new receptor having high affinity and selectivity for malic acid, a guest that differs from tartaric acid by a single oxygen atom. Seven iteratively modified sequences

  对酒石酸具有高亲和力和选择性的合成螺旋芳族寡酰胺折叠体受体通过单体的突变、添加和缺失对其序列进行基于结构的进化，以产生对苹果酸具有高亲和力和选择性的新受体，与酒石酸仅一个氧原子不同的客体。合成了七个反复修改的序列。系统地进行了主客体复合体的详细结构研究，以指导下一代的设计。第一个结果是受体选择性的逆转，对酒石酸的起始偏好超过 10(2)，而结束序列显示对苹果酸的偏好超过酒石酸超过 10(2)。另一个结果是对苹果酸的亲和力大大增强，尽管它通过极性相互作用（如氢键）结合的识别特征较少。类似客人之间的这种区分程度证明了折叠者对分子识别方面的杰出成就的服从性。总而言之，我们的结果证明了一种合理的受体设计方法的可行性，该方法利用折叠体序列的模块化，以及在芳香酰胺折叠体的情况下，它们对结构阐明的顺从性、合成的相对容易性以及其结构的可预测性。类似客人之间的这种区分程度证明了折叠者对分子识别方面的杰出成就