Boc-Phe-Aib-OH | 115723-00-7

• 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-OH
• 英文别名: 2-methyl-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]amino]propanoic acid
• CAS: 115723-00-7
• 化学式: C₁₈H₂₆N₂O₅
• 分子量: 350.415
• InChiKey: QVCGUYBICLKBMF-ZDUSSCGKSA-N

物化性质

• 沸点：
  588.4±50.0 °C(Predicted)
• 密度：
  1.165±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Boc-Phe-Aib-OH 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 82.0h， 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：

  BOC-L-苯丙氨酸 在 sodium hydroxide 、 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 120.0h， 生成 Boc-Phe-Aib-OH
  参考文献：
  名称：

  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

  摘要：

  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。

  DOI：

  10.1039/b415455j

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。
• Tripeptide based super-organogelators: structure and function
  作者：Debasish Podder、Srayoshi Roy Chowdhury、Sujay Kumar Nandi、Debasish Haldar

  DOI：10.1039/c8nj05578e

  日期：——

  tripeptide-based low molecular weight super-organogelators were synthesized and characterized. Four tripeptides with diverse steric crowding at the central amino acid residue were studied. From this series, only sterically less hindered peptide 1 and peptide 3 formed organogels in different saturated hydrocarbons, crude oil, and aromatic solvents. In diesel, the peptides formed gels at 1 wt%, i.e. they

  合成和表征了一系列新颖的基于三肽的低分子量超级有机胶凝剂。研究了在中央氨基酸残基上具有不同空间拥挤的四个三肽。在该系列中，只有位阻较少的肽1和3在不同的饱和烃，原油和芳族溶剂中形成有机凝胶。在柴油中，这些肽以1 wt％的比例形成凝胶，即他们充当超级组织者。有趣的是，两种肽凝胶均显示出高稳定性和显着的自愈特性。由于这些肽具有富电子的苯基系统，因此相应的凝胶还可以与阳离子染料相互作用，并且可以从废水中选择性去除阳离子染料。超级胶凝剂仅从油水两相混合物中固化油具有很高的效率。由于超级胶凝剂在无毒有机溶剂乙醇中的高溶解度，因此该溶液易于处理，只需将乙醇溶液喷洒在油水混合物上，便能够在室温下发挥胶凝作用。可以将有机凝胶下的残留水抽出，并可以通过真空蒸馏从有机凝胶中回收油。因此，超级胶凝剂可以用作低成本，无毒，
• 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.
• Inverse Peptide Synthesis Using Transient Protected Amino Acids
  作者：Tao Liu、Zejun Peng、Manting Lai、Long Hu、Junfeng Zhao

  DOI：10.1021/jacs.4c00314

  日期：2024.2.14

  C → N peptide chemical synthesis. The mandatory use of the Nα-protecting group invokes two additional operations for incorporating each amino acid, resulting in poor step- and atom-economy. The burgeoning demand in the peptide therapeutic market necessitates cost-effective and environmentally friendly peptide manufacturing strategies. Inverse peptide chemical synthesis using unprotected amino acids

  在过去的三十年里，肽疗法经历了快速复兴。虽然少数肽药物是生物生产的，但大多数是通过化学合成生产的。 α-氨基酸氨基的预先保护、羧基的活化、与不断增长的肽链的游离氨基的氨解、N末端的脱保护的循环构成了常规C→N肽的原理化学合成。强制使用 N α -保护基团需要两次额外的操作来掺入每个氨基酸，导致步骤经济性和原子经济性较差。肽治疗市场不断增长的需求需要具有成本效益且环保的肽生产策略。使用未受保护的氨基酸的逆肽化学合成已被认为是一种理想且有吸引力的策略。然而，由于N→C肽链延伸过程中严重的外消旋/差向异构化，该技术在60多年来一直没有成功。在此，这一挑战已通过采用瞬态保护策略的 ynamide 偶联试剂成功解决。活化、瞬时保护、氨解和原位脱保护在一锅中完成，从而提供了一种以未保护的氨基酸为起始原料的实用的肽化学合成策略。肽活性药物成分的合成证明了其稳健性。它还适用于片段缩合和反固相肽合成。与绿色