3-[[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-6-(2-trimethylsilylethoxycarbonylamino)hexanoyl]-[(1S)-1-phenylethyl]amino]propanoic acid | 935674-17-2

• 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: 3-[[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-6-(2-trimethylsilylethoxycarbonylamino)hexanoyl]-[(1S)-1-phenylethyl]amino]propanoic acid
• CAS: 935674-17-2
• 化学式: C₃₈H₄₉N₃O₇Si
• 分子量: 687.908
• InChiKey: HDQSUHCGWRQQQN-FOPBOCKXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.19
• 重原子数：
  49
• 可旋转键数：
  19
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  134
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-[[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-6-(2-trimethylsilylethoxycarbonylamino)hexanoyl]-[(1S)-1-phenylethyl]amino]propanoic acid 、 乙酸酐 、 三氟乙酸 以29%的产率得到
  参考文献：
  名称：

  α-Peptide/β-Peptoid Chimeras

  摘要：

  [GRAPHICS]We describe the synthesis and characterization of the first generation of oligomers consisting of alternating repeats of alpha-amino acids and chiral N-alkyl-beta-alanine (beta-peptoid) residues. These chimeras are stable toward proteolysis, non-hemolytic, and possess antibacterial activity comparable to well-known antimicrobial agents. Moreover, the chimeras exhibit length-dependent, concentration-dependent, solvent-dependent, and ion-strength-dependent ellipticity, indicating the presence of a secondary structure in solution. Thus, alpha-peptide/beta-peptoid oligomers represent a promising novel peptidomimetic backbone construct for biologically active ligands.

  DOI：

  10.1021/ol070316c
• 作为产物：
  描述：

  3-((S)-1-phenyl-ethylamino)-propionic acid tert-butyl ester 在 三氟乙酸 作用下， 生成 3-[[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-6-(2-trimethylsilylethoxycarbonylamino)hexanoyl]-[(1S)-1-phenylethyl]amino]propanoic acid
  参考文献：
  名称：

  α-Peptide/β-Peptoid Chimeras

  摘要：

  [GRAPHICS]We describe the synthesis and characterization of the first generation of oligomers consisting of alternating repeats of alpha-amino acids and chiral N-alkyl-beta-alanine (beta-peptoid) residues. These chimeras are stable toward proteolysis, non-hemolytic, and possess antibacterial activity comparable to well-known antimicrobial agents. Moreover, the chimeras exhibit length-dependent, concentration-dependent, solvent-dependent, and ion-strength-dependent ellipticity, indicating the presence of a secondary structure in solution. Thus, alpha-peptide/beta-peptoid oligomers represent a promising novel peptidomimetic backbone construct for biologically active ligands.

  DOI：

  10.1021/ol070316c

文献信息

• Dimeric Building Blocks for Solid-Phase Synthesis of α-Peptide-β-Peptoid Chimeras
  作者：Christian Olsen、Henrik Franzyk、Gitte Bonke、Line Vedel、Matthias Witt、Jerzy Jaroszewski

  DOI：10.1055/s-2008-1067171

  日期：2008.8

  preparation of a wide range ofdimeric building blocks, displaying different types of side-chains, for use in solid-phase synthesis (SPS) of libraries of this type of oligomers. The β-peptoid monomers were obtained by microwave-assisted aza-Michael additions to acrylic esters. Subsequent solution-phase peptide coupling with suitably protected α-amino acids afforded dimeric intermediates. Even sluggish peptide

  最近，报道了一种具有α-肽-β-拟肽嵌合骨架的新型抗菌和蛋白水解稳定的拟肽寡聚体。本论文描述了用于制备各种二聚体构建块的有效方案，显示不同类型的侧链，用于此类寡聚体库的固相合成 (SPS)。β-类肽单体通过微波辅助氮杂-迈克尔加成到丙烯酸酯中获得。随后的溶液相肽与适当保护的α-氨基酸偶联得到二聚中间体。即使是缓慢的肽偶联，包括空间位阻 N-烷基-β-丙氨酸或具有庞大侧链的氨基酸，在使用微波 (MW) 辐照时也能产生数克级的高产率。保护基团和侧链操作作为一锅溶液相程序进行，以提供十种不同的构件，产率从良好到优异。最后，通过制备 10 到 16 个残基的同聚体并通过组装四种不同的结构单元以产生多种功能化的八聚体，证明了代表性二聚体的 SPS 低聚的效率。