Boc-Phe-Aib-OMe | 115722-99-1

• 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-Phe-Aib-OMe
• 英文别名: methyl 2-methyl-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]amino]propanoate
• CAS: 115722-99-1
• 化学式: C₁₉H₂₈N₂O₅
• 分子量: 364.442
• InChiKey: NOYRLGRKDUQPJF-AWEZNQCLSA-N

物化性质

• 熔点：
  119-121 °C
• 沸点：
  530.8±50.0 °C(Predicted)
• 密度：
  1.117±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Boc-Phe-Aib-OMe 在 sodium hydroxide 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 92.0h， 生成 (2S,3S)-2-[2-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionylamino)-2-methyl-propionylamino]-3-methyl-pentanoic acid
  参考文献：
  名称：

  Can a consecutive double turn conformation be considered as a peptide based molecular scaffold for supramolecular helix in the solid state?

  摘要：

  Helices and sheets are ubiquitous in nature. However, there are also some examples of self-assembling molecules forming supramolecular helices and sheets in unnatural systems. Unlike supramolecular sheets there are a very few examples of peptide sub-units that can be used to construct supramolecular helical architectures using the backbone hydrogen bonding functionalities of peptides. In this report we describe the design and synthesis of two single turn/bend forming peptides (Boc-Phe-Aib-Ile-OMe 1 and Boc-Ala-Leu-Aib-OMe 2) (Aib: alpha-aminoisobutyric acid) and a series of double-turn forming peptides (Boc-Phe-Aib-IIe-Aib-OMe 3, Boc-Leu-Aib-Gly-Aib-OMe 4 and Boc-gamma-Abu-Aib-Leu-Aib-OMe 5) (gamma-Abu: gamma-aminobutyric acid). It has been found that, in crystals, on self-assembly, single turn/bend forming peptides form either a supramolecular sheet (peptide 1) or a supramolecular helix (peptide 2). unlike self-associating double turn forming peptides, which have only the option of forming supramolecular helical assemblages. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.03.057
• 作为产物：
  描述：

  2-amino-2-methylpropionic acid methyl ester 、 BOC-L-苯丙氨酸 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以80%的产率得到Boc-Phe-Aib-OMe
  参考文献：
  名称：

  一种新的二肽作为Cu（II），Zn（II）和Pb（II）的选择性胶凝剂

  摘要：

  已经研究了与将空间约束结合到一系列二肽中有关的各个方面。使用互补的实验方法进行的二肽的自组装倾向使我们能够确定空间限制的影响。含有肽1的Gly和Aib显示出片状形态。肽2中的L- Phe取代Gly会增加空间限制，并导致微棒形成。具有N-苯基甘氨酸和L -Phe的肽3具有花样形态，具有N-苯基甘氨酸和L的肽4-Tyr具有微球形态。固态FT-IR研究表明，这些肽通过氢键自组装。根据X射线晶体学，肽1采用扭结状构象，并通过多个分子间氢键形成超分子反平行片状结构。L- Phe取代Gly有助于肽2呈S形构象并自组装形成固态的超分子螺旋。单晶X射线衍射结果表明，肽3具有扩展的构象，并通过π-π堆积相互作用形成2D片状基质。此外，对于CuSO 4有选择地观察到肽3的金属成对·5H 2 O，ZnSO 4 ·7H 2 O和Pb（OAc）2 ·3H 2 O，而其他金属则不能形成凝胶。这项研究揭示了苯基在二肽的各种自组装中所起的关键作用。

  DOI：

  10.1039/d0ce01199a

文献信息

• β-Turn mimic in tripeptide with Phe(1)-Aib(2) as corner residues and β-strand structure in an isomeric tripeptide: an X-ray diffraction study
  作者：Anita Dutt、Roland Fröhlich、Animesh Pramanik

  DOI：10.1039/b415455j

  日期：——

  A single crystal X-ray diffraction study of the tripeptide Boc-Phe-Aib-Leu-OMe (Aib = α-aminoisobutyric acid) reveals that it forms structurally one of the best type II β-turns so far reported in tripeptides, stabilized by 10 atom intramolecular hydrogen bonding. In contrast, the isomeric tripeptide Boc-Phe-Leu-Aib-OMe adopts a β-strand like conformation. Interestingly, a previously reported structure of another isomeric tripeptide, Boc-Leu-Aib-Phe-OMe, shows a double bend conformation without any intramolecular hydrogen bonding. These results demonstrate an example of the creation of structural diversities in the backbone of small peptides depending upon the co-operative steric interactions amongst the amino acid residues.

  三肽Boc-Phe-Aib-Leu-OMe（Aib为α-氨基异丁酸）的单晶X射线衍射研究表明，它形成了迄今为止在三肽中报道的最佳的II型β转角之一，由10原子内分子氢键稳定。相比之下，异构三肽Boc-Phe-Leu-Aib-OMe采取类似β链的构象。有趣的是，之前报道的另一种异构三肽Boc-Leu-Aib-Phe-OMe的结构显示为无内分子氢键的双弯构象。这些结果展示了小肽主链结构多样性的一个例子，取决于氨基酸残基之间的协同空间相互作用。
• Can a consecutive double turn conformation be considered as a peptide based molecular scaffold for supramolecular helix in the solid state?
  作者：Apurba Kumar Das、Arijit Banerjee、Michael G.B. Drew、Sudipta Ray、Debasish Haldar、Arindam Banerjee

  DOI：10.1016/j.tet.2005.03.057

  日期：2005.5

  Helices and sheets are ubiquitous in nature. However, there are also some examples of self-assembling molecules forming supramolecular helices and sheets in unnatural systems. Unlike supramolecular sheets there are a very few examples of peptide sub-units that can be used to construct supramolecular helical architectures using the backbone hydrogen bonding functionalities of peptides. In this report we describe the design and synthesis of two single turn/bend forming peptides (Boc-Phe-Aib-Ile-OMe 1 and Boc-Ala-Leu-Aib-OMe 2) (Aib: alpha-aminoisobutyric acid) and a series of double-turn forming peptides (Boc-Phe-Aib-IIe-Aib-OMe 3, Boc-Leu-Aib-Gly-Aib-OMe 4 and Boc-gamma-Abu-Aib-Leu-Aib-OMe 5) (gamma-Abu: gamma-aminobutyric acid). It has been found that, in crystals, on self-assembly, single turn/bend forming peptides form either a supramolecular sheet (peptide 1) or a supramolecular helix (peptide 2). unlike self-associating double turn forming peptides, which have only the option of forming supramolecular helical assemblages. (c) 2005 Elsevier Ltd. All rights reserved.
• A new dipeptide as a selective gelator of Cu(<scp>ii</scp>), Zn(<scp>ii</scp>), and Pb(<scp>ii</scp>)
  作者：Santosh Kumar、Sujay Kumar Nandi、Saurav Suman、Debasish Haldar

  DOI：10.1039/d0ce01199a

  日期：——

  morphology. The solid-state FT-IR studies show that the peptides self-assemble by hydrogen bonding. From X-ray crystallography, peptide 1 adopts a kink-like conformation and forms a supramolecular anti-parallel sheet-like structure through multiple intermolecular hydrogen bonds. The replacement of Gly by L-Phe helps peptide 2 to adopt an S-shape conformation and self-assemble to form a supramolecular helix in

  已经研究了与将空间约束结合到一系列二肽中有关的各个方面。使用互补的实验方法进行的二肽的自组装倾向使我们能够确定空间限制的影响。含有肽1的Gly和Aib显示出片状形态。肽2中的L- Phe取代Gly会增加空间限制，并导致微棒形成。具有N-苯基甘氨酸和L -Phe的肽3具有花样形态，具有N-苯基甘氨酸和L的肽4-Tyr具有微球形态。固态FT-IR研究表明，这些肽通过氢键自组装。根据X射线晶体学，肽1采用扭结状构象，并通过多个分子间氢键形成超分子反平行片状结构。L- Phe取代Gly有助于肽2呈S形构象并自组装形成固态的超分子螺旋。单晶X射线衍射结果表明，肽3具有扩展的构象，并通过π-π堆积相互作用形成2D片状基质。此外，对于CuSO 4有选择地观察到肽3的金属成对·5H 2 O，ZnSO 4 ·7H 2 O和Pb（OAc）2 ·3H 2 O，而其他金属则不能形成凝胶。这项研究揭示了苯基在二肽的各种自组装中所起的关键作用。