Boc-Lys(Boc)-Lys(1)-Lys(2)-OMe.Boc-Lys(Boc)-Lys(3)-(2).Boc-Lys(Boc)-(1).Boc-Lys(Boc)-(3) | 391248-71-8

• 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(Boc)-Lys(1)-Lys(2)-OMe.Boc-Lys(Boc)-Lys(3)-(2).Boc-Lys(Boc)-(1).Boc-Lys(Boc)-(3)
• 英文别名: methyl (2S)-2,6-bis[[(2S)-2,6-bis[[(2S)-2,6-bis[(2-methylpropan-2-yl)oxycarbonylamino]hexanoyl]amino]hexanoyl]amino]hexanoate
• CAS: 391248-71-8
• 化学式: C₈₃H₁₅₂N₁₄O₂₄
• 分子量: 1730.2
• InChiKey: VCJWSAMRXJPIBD-NRNPVHEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.6
• 重原子数：
  121
• 可旋转键数：
  66
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  508
• 氢给体数：
  14
• 氢受体数：
  24

反应信息

• 作为反应物：
  描述：

  Boc-Lys(Boc)-Lys(1)-Lys(2)-OMe.Boc-Lys(Boc)-Lys(3)-(2).Boc-Lys(Boc)-(1).Boc-Lys(Boc)-(3) 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成
  参考文献：
  名称：

  Inhibitory Effects of Multivalent Polypeptides on the Proliferation and Metastasis of Breast Cancer Cells

  摘要：

  The susceptibility of peptide drugs to enzymatic degradation has limited their clinical applications. To overcome this limitation, we attached the peptide tyroserleutide (YSL) to a molecular scaffold in order to produce homogeneous monovalent, bivalent, tetravalent, and octavalent YSL dendrimers with highly ordered secondary structures. These multivalent YSL dendrimers were resistant to proteolysis and were better able to induce cytotoxicity in tumor cells in vitro as compared with monomeric peptides. These multivalent YSL dendrimers were also better able to constrain tumor cell metastasis. Compared with monovalent YSL, the multivalent YSL dendrimers displayed enhanced in vivo antitumor activity and suppressed tumor growth and metastasis in BALB/c mice bearing 4T1 tumors. These findings indicate that multivalence can significantly enhance ligand potency and represent a potential method for the development of peptide drugs with high therapeutic potential.

  DOI：

  10.1021/acsmedchemlett.9b00339
• 作为产物：
  描述：

  (S)-2,6-二叔丁氧羰基氨基己酸 、 Lys-Lys(Lys)-OMe 在 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以88%的产率得到Boc-Lys(Boc)-Lys(1)-Lys(2)-OMe.Boc-Lys(Boc)-Lys(3)-(2).Boc-Lys(Boc)-(1).Boc-Lys(Boc)-(3)
  参考文献：
  名称：

  通过点击化学合成具有多面体低聚倍半硅氧烷核的肽树状聚合物

  摘要：

  摘要无机多面体低聚倍半硅氧烷（POSS）是通过铜催化的叠氮化物-炔炔点击化学合成聚（1-赖氨酸）肽树状聚合物的核心。无机/有机复合树枝状聚合物通过MS，1 H NMR，FTIR，GPC和DLS表征。

  DOI：

  10.1016/j.cclet.2013.06.015

文献信息

• Syntheses of dendritic branches based on l-lysine: is the stereochemistry preserved throughout the synthesis?
  作者：Malcolm Driffield、David M. Goodall、David K. Smith

  DOI：10.1039/b304410f

  日期：——

  stereochemistry in the dendritic peptide was dependent on the method of synthesis, with divergent methodology being preferred. The results are discussed in terms of the known stereochemical outcomes of traditional peptide coupling processes, and are generalised to the synthesis of other dendritic peptides. Such observations about the chirality of dendritic peptides are of relevance to chemists developing

  本文报道了基于L-赖氨酸并用Boc或Bz表面基团官能化的单个树枝状分支的合成。采用会聚和发散的合成方法，并使用旋光法，NMR和HPLC监测合成过程中立体化学的保留情况。另外，出于比较目的，合成了基于D，L-赖氨酸的外消旋树枝状分支。观察到树突状肽中立体化学的保留取决于合成方法，优选发散方法。根据传统肽偶联方法的已知立体化学结果讨论了结果，并将其推广到其他树突状肽的合成。
• Controllable mixed-charged co-assembly of dendritic lipopeptides into invisible capsid-like nanoparticles as potential drug carriers
  作者：Qinhan Xu、Chang Shu、Yachao Li、Rong Zhuang、Lei Jiang、Xianghui Xu

  DOI：10.1039/d0cc07953g

  日期：——

  A new type of molecular and supramolecular strategy is proposed to controllably construct mixed-charged nanoparticles with resistance to protein adsorption.

  提出了一种新型的分子和超分子策略，以可控的方式构建具有蛋白质吸附抗性的混合电荷纳米颗粒。
• Supramolecular Solubilisation of Hydrophilic Dyes by Using Individual Dendritic Branches
  作者：Graham M. Dykes、Lisa J. Brierley、David K. Smith、P. Terry McGrail、Gordon J. Seeley

  DOI：10.1002/1521-3765(20011105)7:21<4730::aid-chem4730>3.0.co;2-a

  日期：2001.11.5

  Individual dendritic branches can solubilise hydrophilic dyes in apolar media. The functional group at the focal point of the dendritic branch plays a key role in the dye uptake process. Supramolecular interactions between carboxylic acid and amine groups have been shown to be effective in enabling efficient solubilisation to occur. The necessary complementarity of this interaction is further illustrated by a series of control experiments. The extent of dendritic branching (i.e. dendritic generation) plays a key role in controlling the extent of dye uptake, with higher-generation dendritic branches exhibiting more efficient uptake at lower concentrations. UV/Visible spectroscopic methods have shown that the dendritic branches, in addition to the tuning of the extent of dye uptake, also tune the optical properties of the solubilised dye and this provides further insight into the interactions occurring between the solubilised dye and the individual dendritic branches. Furthermore, it is shown that suitably functionalised dendritic branches can transport hydrophilic dyes through an apolar phase and deliver them continuously into an aqueous medium.