Boc-[18-C-6]-(L)-DOPA-OH | 133343-32-5

• 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: Boc-[18-C-6]-(L)-DOPA-OH
• 英文别名: N^α-Boc-18-crown-6 L-phenylalanine；BOC-18-crown-6 L-phenylalanine；(2S)-3-(2,5,8,11,14,17-hexaoxabicyclo[16.4.0]docosa-1(18),19,21-trien-20-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
• CAS: 133343-32-5
• 化学式: C₂₄H₃₇NO₁₀
• 分子量: 499.558
• InChiKey: CIAFPQDRIDTKCR-IBGZPJMESA-N

物化性质

• 沸点：
  669.3±55.0 °C(Predicted)
• 密度：
  1.149±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  131
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  Boc-[18-C-6]-(L)-DOPA-OH 在 silver benzoate 、 氯甲酸乙酯 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 18.25h， 生成 Boc-[18-C-6]-β³-(L)-DOPA-OMe
  参考文献：
  名称：

  Synthesis of [18-C-6]-β3-(L)-DOPA, first β-amino acid with a crown-ether receptor side-chain

  摘要：

  Terminally protected Boc-beta(3)-(L)-DOPA-OMe has been synthesized from (L)-DOPA by the Arndt-Eistert homologation procedure. Then, a first crown-ether derivative, Boc-[18-C-6]-beta(3)-(L)-DOPA-OMe. has been obtained by bis-O-alkylation of the catechol function with cyclization, using Cs2CO3 as base and pentaethyleneglycol ditosylate as alkylating agent, in DMF at 60degreesC. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02035-x
• 作为产物：
  描述：

  1,14-二溴-3,6,9,12-四恶十四烷 在 sodium hydroxide 、 caesium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 Boc-[18-C-6]-(L)-DOPA-OH
  参考文献：
  名称：

  Design, synthesis, and characterization of peptide nanostructures having ion channel activity

  摘要：

  We report the synthesis and the functional studies of multiple crown a-helical peptides designed to form artificial ion channels. The approach combines the versatility of solid phase peptide synthesis, the conformational predictability of peptidic molecules, and the solution synthesis of crown ethers with engineerable ion-binding abilities. Several biophysical methods were employed to characterize the activity and the mode of action of these crown peptide nanostructures. The 21 residue peptides bearing six 21-EC-7 turned out to facilitate the translocation of ions in a similar fashion to natural ion channels. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.08.037

文献信息

• Crown-ether-modified cyclic dipeptides as supramolecular chiral catalysts
  作者：Christopher Bérubé、Normand Voyer

  DOI：10.1080/10610278.2017.1392521

  日期：2018.3.4

  the objective to develop supramolecular catalysts for useful chemical transformations, we report here a rapid and efficient solid-phase synthesis of novel cyclic dipeptides (crown-CDPs) with a diversity of L-DOPA derived crown ether substituents and stereochemistry. We prepared and characterized 14 crown-CDPs and evaluated their efficiency as supramolecular epoxidation catalysts in a water/hexanes biphasic

  摘要 为了开发用于有用化学转化的超分子催化剂，我们在此报告了一种快速有效的新型环二肽（冠 CDP）的固相合成，具有多种 L-DOPA 衍生的冠醚取代基和立体化学。我们制备并表征了 14 种冠 CDP，并评估了它们在水/己烷双相体系中作为超分子环氧化催化剂的效率。尽管对映选择性取决于取代基的性质，但在冠 CDP 存在下产率显着增加。报告的结果构成了感兴趣的手性环氧化物的有用方法，并进一步说明了环肽作为超分子催化剂的潜力。
• How Far Can a Sodium Ion Travel within a Lipid Bilayer?
  作者：François Otis、Charles Racine-Berthiaume、Normand Voyer

  DOI：10.1021/ja110336s

  日期：2011.5.4

  Analogues of a synthetic ion channel made from a helical peptide were used to study the mechanism of cation translocation within bilayer membranes. Derivatives bearing two, three, four, and six crown ethers used as ion relays were synthesized, and their transport abilities across lipid bilayers were measured. The results showed that the maximum distance a sodium ion is permitted to travel between two

  由螺旋肽制成的合成离子通道的类似物用于研究双层膜内阳离子易位的机制。合成了带有用作离子继电器的两个、三个、四个和六个冠醚的衍生物，并测量了它们跨脂质双层的运输能力。结果表明，钠离子在脂双层环境中的两个结合位点之间移动的最大距离为 11 埃。
• Novel acyclic receptors for aromatic amines using peptidic frameworks
  作者：Normand Voyer、Brigitte Guérin

  DOI：10.1039/c39920001253

  日期：——

  The synthesis, characteristics and recognition ability of a novel class of acyclic peptidic receptors designed to complex aromatic ammonium guests using a combination of hydrogen-bonding, electrostatic and π–π interactions is described.

  本文介绍了一类新型无环多肽受体的合成、特征和识别能力，该受体是利用氢键、静电和 π-π 相互作用的组合来复合芳香族铵客体的。