Boc-Lys(Z)-Phe-OMe | 18671-00-6

• 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: Boc-Lys(Z)-Phe-OMe
• 英文别名: (N'-Benzyloxycarbonyl-N-tert-butoxycarbonyl-Lys)-Phe-methylester；Boc-Lys(Cbz)-Phe-OMe；methyl (2S)-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-6-(phenylmethoxycarbonylamino)hexanoyl]amino]-3-phenylpropanoate
• CAS: 18671-00-6
• 化学式: C₂₉H₃₉N₃O₇
• 分子量: 541.645
• InChiKey: CSTPUZYKIQRSBS-ZEQRLZLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  39
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  132
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Boc-Lys(Z)-Phe-OMe 在 一水合肼 、 苯甲醚 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 Boc-Ala-Ala-Lys(Z)-Phe-NHNH2
  参考文献：
  名称：

  Amino acids and peptides. XIV Synthesis and biological activity of three S-peptide analogues of bovine pancreatic ribonuclease A (RNase A).

  摘要：

  采用片段缩合法合成了牛胰腺核糖核酸酶 A（RNase A）的三种 S 肽类似物，即 [Nle1] [Lys7] S 肽（I）、[Lys1] [Nle7] S 肽（II）和 [Nle1] [Nle7] S 肽（III），并考察了它们重新激活 S 蛋白的能力。结果发现，Lys1 和 Lys7 都在 S 蛋白的再活化过程中发挥作用。

  DOI：

  10.1248/cpb.35.468
• 作为产物：
  描述：

  N-重氮基氨基甲酸叔-丁基酯 在 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 生成 Boc-Lys(Z)-Phe-OMe
  参考文献：
  名称：

  Visser,S. et al., Recueil des Travaux Chimiques des Pays-Bas, 1968, vol. 87, p. 559 - 571

  摘要：

  DOI：

文献信息

• Synthesis of Highly Substituted Imidazolidine-2,4-dione (Hydantoin) through Tf₂O-Mediated Dual Activation of Boc-Protected Dipeptidyl Compounds
  作者：Hui Liu、Zhimin Yang、Zhengying Pan

  DOI：10.1021/ol502900j

  日期：2014.11.21

  Highly substituted chiral hydantoins were readily synthesized from simple dipeptides in a single step under mild conditions. This reaction proceeded through the dual activation of an amide and a tert-butyloxycarbonyl (Boc) protecting group by Tf2O-pyridine. This method was successfully applied in the preparation of a variety of biologically active compounds, including drug analogs and natural products

  高取代度的手性乙内酰脲很容易在温和的条件下一步一步由简单的二肽合成。该反应通过Tf 2 O-吡啶双重活化酰胺和叔丁氧羰基（Boc）保护基而进行。该方法已成功地用于制备多种生物活性化合物，包括药物类似物和天然产物。
• Stimuli‐Responsive Supramolecular Gelation in Ferrocene–Peptide Conjugates
  作者：Rouzbeh Afrasiabi、Heinz‐Bernhard Kraatz

  DOI：10.1002/chem.201302450

  日期：2013.12.16

  Teaching an old dog new tricks: Ferrocene–dipeptide conjugates capable of forming gels in response to various external signals including sound, thermal, redox, and mechanical stress are reported (see figure). Interesting examples of how ferrocene–peptide conjugates can be exploited for the construction of organometallic gelators are demonstrated.

  教老狗新的技巧：据报道，二茂铁-二肽结合物能够响应各种外部信号，包括声音，热，氧化还原和机械应力而形成凝胶（见图）。展示了如何利用二茂铁-肽共轭物构建有机金属胶凝剂的有趣例子。
• Small-Peptide-Based Organogel Kit: Towards the Development of Multicomponent Self-Sorting Organogels
  作者：Rouzbeh Afrasiabi、Heinz-Bernhard Kraatz

  DOI：10.1002/chem.201303116

  日期：2013.11.18

  possible future applications of similar systems in the development of a supramolecular photo‐conversion device. Interestingly, it was observed that the self‐organization of the components can lead to highly ordered systems in which discrimination between compatible and non‐compatible building blocks directs the effective organization of the chromophores and gives rise to the formation of an excited‐state

  此处给出的结果突出了超短肽作为智能多组分超分子设备开发中的基本组成部分的极其有用的性质。基于超短肽的预测性自组装，已经提出了一种简便的自下而上的策略，用于合成一个小的刺激响应型智能有机胶凝剂库。更重要的是，已经对自恋者对凝胶的自选进行了评估，以此作为一种有效共组装供体-受体双组分凝胶的简单方法，从而可以研究类似系统在超分子开发中的未来可能应用光电转换设备。有趣的是，据观察，组分的自组织可导致高度有序的系统，其中相容性和非相容性结构单元之间的区别将指导发色团的有效组织，并导致形成具有激基复合物的激发态复合物。像发射。本报告可能对开发基于有机凝胶的多组分智能设备很重要。
• Rational Design and Application of a Redox-Active, Photoresponsive, Discrete Metallogelator
  作者：Rouzbeh Afrasiabi、Heinz-Bernhard Kraatz

  DOI：10.1002/chem.201500704

  日期：2015.5.18

  A photoresponsive discrete metallogelator was rationally designed by incorporating a photochromic azobenzene subunit in the structure of a redox‐active ferrocene–peptide conjugate. The target molecule was purposefully equipped with a dipeptide unit capable of self‐assembly in response to sonication. The designed molecule was shown to undergo supramolecular self‐assembly and achieve organogelation in

  通过将光致变色偶氮苯亚基掺入氧化还原活性二茂铁-肽共轭物的结构中，对光敏离散金属成对剂进行了合理设计。目标分子特意配备了能够根据声波自组装的二肽单元。所设计的分子被证明具有超分子自组装能力，并能响应超声，光，热和氧化还原信号而实现有机凝胶化。发现设计的凝胶器的溶胶-凝胶相变对大量的输入刺激敏感，从而允许在基本逻辑门操作中应用溶胶-凝胶的转变行为。当通过使用不同的氧化剂检查有机凝胶的氧化还原活性时，实现了基于凝胶的非逻辑门操作。
• Synthesis and Characterization of Peptide−Cationic Steroid Antibiotic Conjugates
  作者：Bangwei Ding、Uale Taotofa、Thomas Orsak、Matthew Chadwell、Paul B. Savage

  DOI：10.1021/ol048845t

  日期：2004.9.1

  New cationic steroid antibiotics have been prepared by conjugating tripeptides to a triamino analogue of cholic acid. These compounds were synthesized on a solid phase in an indexed library that was screened for antibacterial activity against Gram-negative and Gram-positive bacteria. Selected compounds were synthesized on a larger scale, and minimum inhibition concentrations were measured. These results correlated very well with the screening of the indexed library of antibiotics. The most active antibiotics demonstrate a marked improvement over a related and well characterized cationic steroid antibiotic.