(2S)-2-amino-N-[(2S)-1-[2-[bis[2-[[(2S)-2-[[(2S)-2-amino-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]ethyl]amino]ethylamino]-1-oxo-3-phenylpropan-2-yl]-3-phenylpropanamide | 1419186-32-5

• 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: (2S)-2-amino-N-[(2S)-1-[2-[bis[2-[[(2S)-2-[[(2S)-2-amino-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]ethyl]amino]ethylamino]-1-oxo-3-phenylpropan-2-yl]-3-phenylpropanamide
• CAS: 1419186-32-5
• 化学式: C₆₀H₇₂N₁₀O₆
• 分子量: 1029.3
• InChiKey: WQURAIPGTFSQDW-ZOPNQXNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  76
• 可旋转键数：
  30
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  256
• 氢给体数：
  9
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  tert-butyl N-[(2S)-1-[[(2S)-1-[2-[bis[2-[[(2S)-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]ethyl]amino]ethylamino]-1-oxo-3-phenylpropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]carbamate 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 3.0h， 以0.07 g的产率得到(2S)-2-amino-N-[(2S)-1-[2-[bis[2-[[(2S)-2-[[(2S)-2-amino-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]ethyl]amino]ethylamino]-1-oxo-3-phenylpropan-2-yl]-3-phenylpropanamide
  参考文献：
  名称：

  Spacer driven morphological twist in Phe-Phe dipeptide conjugates

  摘要：

  Chemists and material scientists are interested in complex biological systems and morphologies for fabrication of new materials. Bioinspired design of short peptide conjugates produces various self-assembled structures, depending on their structural diversity. Phe-Phe aromatic dipeptide is an interesting candidate for designing variety of molecular scaffolds. This report describes the synthesis of two symmetrical peptide conjugates by a coupling with C2 and C3 symmetric functional linker's, which spontaneously generate different self-assembled ultra-structures. C2 Symmetric, ethylene diamine linker, conjugated two Phe-Phe dipeptides and produced Phe-Phe-EDA-Phe-Phe (5), which undergoes spontaneous self-assembly to form fibrillar morphology, while C3 symmetric tris(2-aminoethylamine) conjugated three Phe-Phe dipeptides, produced (Phe-Phe)(3)TREN (7) resulted in spherical morphology structures interconnected by fibers. A rational design of two peptide conjugates, by introducing two different linker's, direct different self-assemble pathway, which result in distinct morphologies. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.12.063

文献信息

• Proteinase K-Catalyzed Synthesis of Linear and Star Oligo(<scp>l</scp>-phenylalanine) Conjugates
  作者：Jose M. Ageitos、Peter J. Baker、Michihiro Sugahara、Keiji Numata

  DOI：10.1021/bm4009974

  日期：2013.10.14

  Chemoenzymatic synthesis of peptides is a, and clean chemical reaction that offers high yields without using organic synthesis and serves as an alternative to traditional peptide synthesis methods. This report describes the chemoenzymatic synthesis of oligo(L-phenylalanine) mediated by proteinase K from Tritirachium album, which is one of the most widely used proteases in molecular biological studies. The synthesized linear oligo-phenylalanine showed a unique self-assembly in aqueous solutions. To further functionalize linear oligo(L-phenylalanine) as a low-molecular-weight gelator, it was cosynthesized with tris(2-aminoethyl)amine to obtain star-oligo(L-phenylalanine), which was bioconjugated to demonstrate its self-assembly into fluorescent fibers. The self-assembled fibers of star-oligo(L-phenylalanine) formed fibrous networks with various branching ratios, which depended on the molecular weights and molecular aspect ratios of star-oligo(L-phenylalanine). This is the first study to demonstrate that proteinase K is a suitable enzyme for chemoenzymatic cosynthesis of oligopeptides and star-shaped heteropeptides.