2-[6-[(2-Methylpropan-2-yl)oxycarbonylamino]hexylamino]acetic acid | 174799-99-6

• 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: 2-[6-[(2-Methylpropan-2-yl)oxycarbonylamino]hexylamino]acetic acid
• CAS: 174799-99-6
• 化学式: C₁₃H₂₆N₂O₄
• 分子量: 274.36
• InChiKey: IXFYTNVPXKHGOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  19
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  87.7
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[6-[(2-Methylpropan-2-yl)oxycarbonylamino]hexylamino]acetic acid 以 水 、 乙腈 为溶剂， 反应 0.75h， 生成 5-[[6-[6-Aminohexyl-[2-[6-aminohexyl-[2-[6-aminohexyl-[2-[6-aminohexyl-[2-[6-aminohexyl-(2-amino-2-oxoethyl)amino]-2-oxoethyl]amino]-2-oxoethyl]amino]-2-oxoethyl]amino]-2-oxoethyl]amino]-6-oxohexyl]carbamoyl]-2-(3-hydroxy-6-oxoxanthen-9-yl)benzoic acid
  参考文献：
  名称：

  Cell penetrable peptoid carrier vehicles: synthesis and evaluationElectronic supplementary information (ESI) available: experimental details. See http://www.rsc.org/suppdata/cc/b3/b306438g/

  摘要：

  使用高效的固相合成方法合成了一系列与荧光素偶联的肽分子寡聚物，并观察到它们显示出显著的细胞穿透特性，这为高效的细胞靶向提供了可能性。

  DOI：

  10.1039/b306438g
• 作为产物：
  描述：

  tert-butyl N-[6-(benzylamino)hexyl]carbamate 在 palladium on activated charcoal 氢气 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、413.69 kPa 条件下， 反应 7.5h， 生成 2-[6-[(2-Methylpropan-2-yl)oxycarbonylamino]hexylamino]acetic acid
  参考文献：
  名称：

  Building Units for N-Backbone Cyclic Peptides. 3. Synthesis of Protected N^α-(ω-Aminoalkyl)amino Acids and N^α-(ω-Carboxyalkyl)amino Acids

  摘要：

  An improved synthesis of a family of amino acids that contain omega-aminoalkyl groups and of a new family containing omega-carboxyalkyl groups linked to the alpha-amine is described. The synthesis was performed by alkylation of suitably monoprotected alkylenediamines and protected omega-amino acids with triflates of alpha-hydroxy acid esters. The reaction proceeded with inversion of configuration yielding optically pure products. The N-alpha-(omega-aminoalkyl)amino acids and N-alpha-(omega-carboxyalkyl)amino acids were orthogonally protected to allow their incorporation into peptides by solid-phase peptide synthesis (SPPS) methodology.

  DOI：

  10.1021/jo961580e

文献信息

• Flow and Microwave-Assisted Synthesis of <i>N</i>-(Triethylene glycol)glycine Oligomers and Their Remarkable Cellular Transporter Activities
  作者：ThingSoon Jong、Ana M. Pérez-López、Emma M. V. Johansson、Annamaria Lilienkampf、Mark Bradley

  DOI：10.1021/acs.bioconjchem.5b00307

  日期：2015.8.19

  respectively. These were converted into oligomers (5, 7, and 9-mers) using an Fmoc-based solid-phase protocol and evaluated as cellular transporters. Hybrid oligomers, constructed of alternating units of the aminohexyl and amino-TEG monomers, were non-cytotoxic and exhibited remarkable cellular uptake activity compared to the analogous fully TEG or lysine-like compounds.

  拟肽，例如寡-N-烷基甘氨酸（类肽），由于其强大的蛋白水解稳定性和降低的细胞毒性，因此是传统阳离子穿透细胞肽（例如R 9）的有吸引力的替代物。这里，单体Ñ -alkylglycines，结合氨基官能化己基或三甘醇（TEG）侧链，分别通过三步骤连续流动反应序列合成，得到单体Ñ -Fmoc-（6-叔丁氧羰氨基己基）甘氨酸和ñ-Fmoc-（（2-（2-Boc-氨基乙氧基）乙氧基）乙基）甘氨酸的总收率分别为49％和41％。使用基于Fmoc的固相方案将它们转化为寡聚体（5、7和9聚体），并作为细胞转运蛋白进行评估。由氨基己基和氨基-TEG单体的交替单元构成的杂化低聚物，与类似的完全TEG或赖氨酸样化合物相比，具有无细胞毒性，并显示出显着的细胞摄取活性。
• Peptoid dendrimers—microwave-assisted solid-phase synthesis and transfection agent evaluation
  作者：Juan J. Diaz-Mochon、Mario A. Fara、Rosario M. Sanchez-Martin、Mark Bradley

  DOI：10.1016/j.tetlet.2007.11.122

  日期：2008.1

  Three generations of peptoid-based dendrimers were synthesised by solid-phase methods, using N-Fmoc-N-(6-N'-Fmoc-aminohexyl)glycine as both the initiator core and the monomer unit, which offer an unusual dendrimeric periphery composed of both secondary and primary amines. The third generation compound proved to be an efficient mediator of transfection while displaying minimal cytotoxicity. (C) 2007 Elsevier Ltd. All rights reserved.
• Building units for N-backbone cyclic peptides. 1. Synthesis of protected N-(.omega.-aminoalkylene)amino acids and their incorporation into dipeptide units
  作者：Gerardo Byk、Chaim Gilon

  DOI：10.1021/jo00047a022

  日期：1992.10

  A variety of new amino acids which contain an omega-aminoalkylene group on the N(alpha)-amino nitrogen were synthesized by alkylation of alkylenediamines with alpha-halogeno acids. The reaction proceeds with inversion of configuration; thus, optically pure products were obtained when optically active a-halogeno acids were used. The N-(omega-aminoalkylene)amino acids were protected by orthogonal protecting groups to allow their incorporation into dipeptides by the "solution" techniques and into peptides by the solid-phase peptide synthesis (SPPS) methodology. A series of dipeptide analogs of Phe-Gly, Leu-Gly, Trp-Gly, Phe-Leu, and Phe-Ala in which the nitrogen of the peptide bond is alkylated by omega-aminoalkylene chains with various lengths were prepared. These new protected N-(omega-aminoalkylene)amino acids and their derived dipeptide units may be used as building blocks for conformationally constrained N-backbone cyclic peptides.
• Cell penetrable peptoid carrier vehicles: synthesis and evaluationElectronic supplementary information (ESI) available: experimental details. See http://www.rsc.org/suppdata/cc/b3/b306438g/
  作者：Ilaria Peretto、Rosario M. Sanchez-Martin、Xui-hong Wang、John Ellard、Stifun Mittoo、Mark Bradley

  DOI：10.1039/b306438g

  日期：——

  Using a highly efficient solid-phase route a series of fluorescein conjugated peptoid oligomers were synthesised and observed to display remarkable cell penetrating properties, offering the possibility of highly efficient cellular targeting.

  使用高效的固相合成方法合成了一系列与荧光素偶联的肽分子寡聚物，并观察到它们显示出显著的细胞穿透特性，这为高效的细胞靶向提供了可能性。
• Building Units for N-Backbone Cyclic Peptides. 3. Synthesis of Protected <i>N</i>^α-(ω-Aminoalkyl)amino Acids and <i>N</i>^α-(ω-Carboxyalkyl)amino Acids
  作者：Dan Muller、Irena Zeltser、Gal Bitan、Chaim Gilon

  DOI：10.1021/jo961580e

  日期：1997.1.1

  An improved synthesis of a family of amino acids that contain omega-aminoalkyl groups and of a new family containing omega-carboxyalkyl groups linked to the alpha-amine is described. The synthesis was performed by alkylation of suitably monoprotected alkylenediamines and protected omega-amino acids with triflates of alpha-hydroxy acid esters. The reaction proceeded with inversion of configuration yielding optically pure products. The N-alpha-(omega-aminoalkyl)amino acids and N-alpha-(omega-carboxyalkyl)amino acids were orthogonally protected to allow their incorporation into peptides by solid-phase peptide synthesis (SPPS) methodology.