octyl 3-amino-5-[(5'-hexanoamido-2'-octyloxy)phenylcarbonylaminomethyl-carbonylamino]benzoate | 345625-93-6

• 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: octyl 3-amino-5-[(5'-hexanoamido-2'-octyloxy)phenylcarbonylaminomethyl-carbonylamino]benzoate
• 英文别名: Octyl 3-amino-5-[[2-[[5-(hexanoylamino)-2-octoxybenzoyl]amino]acetyl]amino]benzoate
• CAS: 345625-93-6
• 化学式: C₃₈H₅₈N₄O₆
• 分子量: 666.902
• InChiKey: XGUQORDOUDFBEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  48
• 可旋转键数：
  26
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  149
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  octyl 3-amino-5-[(5'-hexanoamido-2'-octyloxy)phenylcarbonylaminomethyl-carbonylamino]benzoate 在 palladium on activated charcoal 盐酸 、 氢气 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-[2-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-acetylamino]-5-[2-(5-hexanoylamino-2-octyloxy-benzoylamino)-acetylamino]-benzoic acid octyl ester
  参考文献：
  名称：

  A Noncovalent Approach to Antiparallel β-Sheet Formation

  摘要：

  Four tripeptide chains, when attached to the same end of a hydrogen-bonded duplex (1.2) with the unsymmetrical, complementary sequences of ADAA/DADD, have been brought into proximity, leading to the formation of four hybrid duplexes, 1a.2a, 1a.2b, 1b.2a, and 1b.2b, each of which contains a two-stranded beta-sheet segment. The extended conformations of the peptide chains were confirmed by 1D and 2D NMR. The peptide strands stay registered through hydrogen bonding and the beta-sheets are stabilized by side chain interactions. Two-dimensional NMR data also indicate that the duplex template prevents further aggregation in the peptide segment. When the peptide chains are attached to the two different termini of the duplex template, NMR studies show the presence of a mixture with no clearly defined conformations. In the absence of the duplex template, the tripeptides are found to associate randomly. Finally, isothermal titration calorimetry studies revealed that the hybrid duplex 1a.2a was more stable than either the duplex template or the peptides alone.

  DOI：

  10.1021/ja010701b
• 作为产物：
  描述：

  N-((ethoxycarbonyl)methyl)-5-amino-2-(octyloxy)benzamide 在 sodium hydroxide 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 12.5h， 生成 octyl 3-amino-5-[(5'-hexanoamido-2'-octyloxy)phenylcarbonylaminomethyl-carbonylamino]benzoate
  参考文献：
  名称：

  氢键分子双链体的序列特异性。

  摘要：

  基于双链体1.2设计并合成了氢键结合的分子双链体1.3和1.4，它们各自包含一个不匹配的结合位点（1.3中的受体对受体，以及1.4中的供体对受体）。一维和二维NMR研究表明，尽管存在单个错配的结合位点，但双链体1.3和1.4的骨架仍通过形成其余五个H键而保持对准。1.3和1.4的骨架通过在这些位点周围轻微扭曲而调整为存在不匹配的结合位点，从而减轻了两个H键供体（酰胺O）之间或两个受体（酰胺H）之间的正面排斥性相互作用。将1当量的单链2与单链1形成完美匹配的双链体1.2后，添加到1.3或1.4的溶液中，仅添加1.2和单链3或4，被检测到。等温滴定量热法（ITC，在含5％DMSO的氯仿中）表明，双链体1.3和1.4的稳定性比相应的氢键结合的双链体1.2的稳定性差（> 40倍）。这些NMR和ITC结果表明，两条互补单链的配对不受另一条非常相似的单链的影响，后者仅包含一个错误的H键供体或受体，这表

  DOI：

  10.1021/jo010250d

文献信息

• Amphiphilic oligoamides as versatile, acid-responsive gelators
  作者：Qiang Pei、Quan Tang、Zheng-Li Tan、Zhong-Lin Lu、Lan He、Bing Gong

  DOI：10.1039/c7ra03074f

  日期：——

  revealed G2 as a versatile gelator capable of forming stable hydrogels as well as several organogels. From UV, fluorescence, NMR, and SEM studies, the formation of hydrogels is driven by hydrophobic forces and π–π stacking while the gelation of nonpolar organic solvents relies on hydrogen-bonding interactions. The hydrogel of G2 is able to encapsulate and release medicinally important polar substances

  设计并合成了六种具有相同主链但侧链和端链不同的寡酰胺，G1-G6。筛选这些低聚酰胺的胶凝能力表明，G2是一种多功能胶凝剂，能够形成稳定的水凝胶以及几种有机凝胶。从UV，荧光，NMR和SEM研究来看，水凝胶的形成是由疏水力和π-π堆积驱动的，而非极性有机溶剂的凝胶化则依赖于氢键相互作用。G2的水凝胶能够将具有医学重要意义的极性物质包囊并释放到水中，并具有酸响应性。
• Sequence Specificity of Hydrogen-Bonded Molecular Duplexes
  作者：Huaqiang Zeng、Harold Ickes、Robert A. Flowers、Bing Gong

  DOI：10.1021/jo010250d

  日期：2001.5.1

  perfectly hydrogen-bonded duplex 1.2. These NMR and ITC results indicate that the pairing of two complementary single strands is not affected by another very similar single strand that contains only one wrong H-bond donor or acceptor, which demonstrates that the self-assembly of this class of H-bonded duplexes is a highly sequence-specific process. The role of these H-bonded duplexes as predictable and programmable

  基于双链体1.2设计并合成了氢键结合的分子双链体1.3和1.4，它们各自包含一个不匹配的结合位点（1.3中的受体对受体，以及1.4中的供体对受体）。一维和二维NMR研究表明，尽管存在单个错配的结合位点，但双链体1.3和1.4的骨架仍通过形成其余五个H键而保持对准。1.3和1.4的骨架通过在这些位点周围轻微扭曲而调整为存在不匹配的结合位点，从而减轻了两个H键供体（酰胺O）之间或两个受体（酰胺H）之间的正面排斥性相互作用。将1当量的单链2与单链1形成完美匹配的双链体1.2后，添加到1.3或1.4的溶液中，仅添加1.2和单链3或4，被检测到。等温滴定量热法（ITC，在含5％DMSO的氯仿中）表明，双链体1.3和1.4的稳定性比相应的氢键结合的双链体1.2的稳定性差（> 40倍）。这些NMR和ITC结果表明，两条互补单链的配对不受另一条非常相似的单链的影响，后者仅包含一个错误的H键供体或受体，这表
• Effective formation of stable and versatile double-stranded β-sheets templated by a hydrogen-bonded duplex
  作者：You-Di Shi、Quan Tang、Ya-Fei Jiang、Qiang Pei、Hong-Wei Tan、Zhong-Lin Lu、Bing Gong

  DOI：10.1039/c8cc01564c

  日期：——

  We report herein an effective approach that is generally applicable for constructing double-stranded β-sheets composed of tetra- and penta-peptides based on a hydrogen-bonded duplex template, regardless of their amino acid sequences and α-helical or β-sheet propensities.

  我们在此报告了一种有效的方法，该方法通常可用于构建基于氢键合双链模板的由四肽和五肽组成的双链β-折叠，而不管其氨基酸序列和α-螺旋或β-折叠的倾向如何。
• A Noncovalent Approach to Antiparallel β-Sheet Formation
  作者：Huaqiang Zeng、Xiaowu Yang、Robert A. Flowers、Bing Gong

  DOI：10.1021/ja010701b

  日期：2002.3.1

  Four tripeptide chains, when attached to the same end of a hydrogen-bonded duplex (1.2) with the unsymmetrical, complementary sequences of ADAA/DADD, have been brought into proximity, leading to the formation of four hybrid duplexes, 1a.2a, 1a.2b, 1b.2a, and 1b.2b, each of which contains a two-stranded beta-sheet segment. The extended conformations of the peptide chains were confirmed by 1D and 2D NMR. The peptide strands stay registered through hydrogen bonding and the beta-sheets are stabilized by side chain interactions. Two-dimensional NMR data also indicate that the duplex template prevents further aggregation in the peptide segment. When the peptide chains are attached to the two different termini of the duplex template, NMR studies show the presence of a mixture with no clearly defined conformations. In the absence of the duplex template, the tripeptides are found to associate randomly. Finally, isothermal titration calorimetry studies revealed that the hybrid duplex 1a.2a was more stable than either the duplex template or the peptides alone.