benzyl (6-(tert-butoxycarbonylamino)hexylamino)-acetate | 1137504-29-0

• 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: benzyl (6-(tert-butoxycarbonylamino)hexylamino)-acetate
• CAS: 1137504-29-0
• 化学式: C₂₀H₃₂N₂O₄
• 分子量: 364.485
• InChiKey: QRSVORURYNYWOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  26.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  76.66
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  benzyl (6-(tert-butoxycarbonylamino)hexylamino)-acetate 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 28.0h， 生成
  参考文献：
  名称：

  Fullerene bisadduct regioisomers containing an asymmetric diamide tether

  摘要：

  Four macrocyclic bis(pyrrolidino)fullerene regioisomers with e-edge, e-face, trans-4 and cis-2 addition patterns were synthesized from the corresponding monoadduct by Prato's cycloaddition in a yield of 50%, and fully characterized by spectroscopic techniques. Bisadduct regioisomers were isolated easily in a pure form using dry-flash column chromatography. The relative ratio of the isolated regioisomers e-edge/e-face/trans-41cis-2 was 1.0:1.9:1.5:4.9. Morphology of self-assembled structures of the four bisadduct regioisomers in solution was characterized using scanning electron microscopy. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2017.10.069
• 作为产物：
  描述：

  1,6-己二胺 在 三乙胺 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 48.0h， 生成 benzyl (6-(tert-butoxycarbonylamino)hexylamino)-acetate
  参考文献：
  名称：

  Fullerene bisadduct regioisomers containing an asymmetric diamide tether

  摘要：

  Four macrocyclic bis(pyrrolidino)fullerene regioisomers with e-edge, e-face, trans-4 and cis-2 addition patterns were synthesized from the corresponding monoadduct by Prato's cycloaddition in a yield of 50%, and fully characterized by spectroscopic techniques. Bisadduct regioisomers were isolated easily in a pure form using dry-flash column chromatography. The relative ratio of the isolated regioisomers e-edge/e-face/trans-41cis-2 was 1.0:1.9:1.5:4.9. Morphology of self-assembled structures of the four bisadduct regioisomers in solution was characterized using scanning electron microscopy. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2017.10.069

文献信息

• Synthesis, penetrability and intracellular targeting of fluorescein-tagged peptoids and peptide–peptoid hybrids
  作者：Asier Unciti-Broceta、Franziska Diezmann、Chiung Ying Ou-Yang、Mario Antonio Fara、Mark Bradley

  DOI：10.1016/j.bmc.2008.02.068

  日期：2009.2

  microwave based solid-phase chemistry a series of fluorescein-labelled cationic peptoid conjugates were synthesized within 24 h and cellular uptake into HeLa, L929 and K562 cells examined via flow cytometry. As expected, analysis revealed that longer oligomers achieved greater cellular penetration (7e (9 mer) > 7d (7 mer) > 7c (5 mer) > 7b (3 mer) > 7a (1 mer)) with the nonamer 7e proving to be a remarkable

  寻找新颖、普遍适用且高效的递送工具是生物技术领域的一项主要活动。使用高度优化的基于微波的固相化学，在 24 小时内合成了一系列荧光素标记的阳离子类肽缀合物，并通过流式细胞术检查细胞摄取到 HeLa、L929 和 K562 细胞中。正如预期的那样，分析表明，较长的低聚物取得了更大的细胞渗透（7E（9聚体）>  7D（7聚体）>  7c中（5聚体）> 图7b（3聚体）> 图7a与九聚物（1聚体））7E被证明是所有细胞系的卓越载体，显示出对 K562 和 L929 细胞的出色渗透性以及对 HeLa 细胞的非凡细胞递送。共聚焦显微镜显示，混合拟肽-核定位序列（来自猿猴病毒 40 大 T 抗原的 PKKKRKV）在 3 小时后导致非常高水平的核递送，开辟了一系列应用，例如活细胞的核染色与非DNA嵌入荧光探针。
• 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。