Boc-Lys(2-chlorocarbobenzoxy)-OH | 195869-14-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Boc-Lys(2-chlorocarbobenzoxy)-OH
• 英文别名: (2-Cl-Z)-L-Lys(Boc)；(2-Cl-Z)-Lys(Boc)OH；(2-Cl-Z)Lys(Boc)OH；Cbz(2-Cl)-Lys(Boc)-OH；(2S)-2-[(2-chlorophenyl)methoxycarbonylamino]-6-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoic acid
• CAS: 195869-14-8
• 化学式: C₁₉H₂₇ClN₂O₆
• 分子量: 414.886
• InChiKey: JYYUGUDJVSMLTN-HNNXBMFYSA-N

物化性质

• 沸点：
  608.3±55.0 °C(Predicted)
• 密度：
  1.236±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Boc-Lys(2-chlorocarbobenzoxy)-OH 、 N,N'-tetrakis(aminoethylaminocarbonylethyl)-L-lysine tryptamide 在 N-羟基丁二酰亚胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成
  参考文献：
  名称：

  On the Antimicrobial Activity of Various Peptide-Based Dendrimers of Similar Architecture

  摘要：

  抗菌药物耐药性是对人类健康的重大威胁。在众多尝试解决这一问题的方法中，合成模拟天然抗菌肽的抗菌化合物似乎是一种有前景的途径。基于肽的树枝状大分子可以设计成比天然抗菌肽具有更高的效力，同时又能避开细菌的防御系统。设计了一类新型树枝状大分子，它们具有相似的化学结构，但最小抑菌浓度方面的效力不同。研究了树枝状大分子结构与抗菌活性之间的关系，以及它们攻击模型细胞膜的能力。数据表明，破坏细胞膜的主要驱动力是超分子结构中的电荷分布和两亲性，而不是净电荷，这与树枝状大分子的溶血活性有很好的相关性。

  DOI：

  10.3390/molecules20010738

文献信息

• Design of Antimicrobially Active Small Amphiphilic Peptide Dendrimers
  作者：Piotr Polcyn、Margarita Jurczak、Aleksandra Rajnisz、Jolanta Solecka、Zofia Urbanczyk-Lipkowska

  DOI：10.3390/molecules14103881

  日期：——

  Novel polyfunctional small amphiphilic peptide dendrimers characterized by incorporation of a new core compounds - tris-amino acids or tetrakis-amino alcohols that originated from a series of basic amino acids - were efficiently synthesized. These new core elements yielded molecules with multiple branching and (+5)/(+6) charge at the 1-st dendrimer generation. Dendrimers exhibited significant antimicrobial

  高效合成了新型多功能小两亲肽树枝状聚合物，其特征是引入了一种新的核心化合物——源自一系列碱性氨基酸的三氨基酸或四氨基醇。这些新的核心元素在第 1 代树枝状聚合物时产生了具有多个分支和 (+5)/(+6) 电荷的分子。树枝状聚合物对革兰 (+) 和革兰 (-) 菌株表现出显着的抗菌效力，还涉及多重耐药参考菌株（金黄色葡萄球菌 ATCC 43300 和大肠杆菌 ATCC BAA-198）。此外，检测到对念珠菌属真菌的高活性。更多带电和更疏水的肽树枝状聚合物表现出溶血特性。
• Novel Antimicrobial Peptide Dendrimers with Amphiphilic Surface and Their Interactions with Phospholipids — Insights from Mass Spectrometry
  作者：Piotr Polcyn、Paulina Zielinska、Magdalena Zimnicka、Anna Troć、Przemysław Kalicki、Jolanta Solecka、Anna Laskowska、Zofia Urbanczyk-Lipkowska

  DOI：10.3390/molecules18067120

  日期：——

  A series of new peptide dendrimers with amphiphilic surface, designed around a dendronized ornithine (Orn) core were synthesized and characterized by ESI-MS, 1H-, 13C- NMR, and CD spectrometry. An improved antimicrobial potency against S. aureus and E. coli was detected as a result of an increased charge, higher branching and variable lipophilicity of the residues located at the C-terminus. Minimal inhibitory concentration (MIC) values indicated that the selected dendrimers were not sensitive to the physiological concentration of Na+ and K+ ions (100 mM), but expressed reduced potency at 10 mM concentration of Mg2+ and Ca2+ ions. Circular dichroism (CD) curves measured under various conditions revealed structure and solvent-dependent curve evolution. ESI-MS studies of gas-phase interactions between selected dendrimers and both anionic (DMPG) and neutral (DMPC) phospholipids revealed the presence of variously charged dendrimer/phospholipid aggregates with 1:1 to 1:5 stoichiometry. The collision-induced fragmentation (CID) of the most abundant [dendrimer/phospholipid]2+ ions of the 1:1 stoichiometry demonstrated that the studied dendrimers formed stronger complexes with anionic DMPG. Both phospholipids have higher affinity towards dendrimers with a more compact structure. Higher differences in CID energy necessary for dissociation of 50% of the complex formed by dendrimers with DMPG vs. DMPC (DCID50) correlate with a lower hemotoxicity. Mass spectrometry results suggest that for a particular group of compounds the DCID50 might be one of the important factors explaining selectivity of antimicrobial peptides and their branched analogs targeting the bacterial membrane. Both circular dichroism and mass spectrometry studies demonstrated that dendrimers of Nα- and Nε-series possess a different conformation in solution and different affinity to model phospholipids, what might influence their specific microbicidal mechanism.

  一系列新型的具有两亲性表面的肽树枝状聚合物以树枝状的鸟氨酸（Orn）为核心进行了合成和表征，通过ESI-MS、1H-、13C-NMR和CD光谱进行了分析。随着带电荷的增加、分支结构的提高以及C末端残基的脂溶性变化，观察到其对金黄色葡萄球菌（S. aureus）和大肠杆菌（E. coli）表现出更强的抗菌活性。最小抑菌浓度（MIC）值表明所选树枝状聚合物对生理浓度的Na+和K+离子（100 mM）不敏感，但在10 mM浓度的Mg2+和Ca2+离子下抗菌活性明显降低。在不同条件下测得的圆二色性（CD）曲线显示出结构和溶剂依赖性曲线演变。选定的树枝状聚合物与阴离子（DMPG）和中性（DMPC）磷脂之间的气相相互作用的ESI-MS研究显示出存在各种带电的树枝状聚合物/磷脂聚集物，比例范围为1:1到1:5。具有1:1比例的最丰富的[dendrimer/phospholipid]2+离子的碰撞诱导碎裂（CID）表明所研究的树枝状聚合物与阴离子DMPG形成了更强的复合物。这两种磷脂对具有更紧凑结构的树枝状聚合物的亲和力更高。DMPG与DMPC所形成树枝状聚合物复杂体的50%解离所需的CID能量差（DCID50）较大，且与较低的血液毒性相对应。质谱结果表明，对于特定的一类化合物，DCID50可能是解释抗菌肽及其支化类似物选择性靶向细菌膜的重要因素之一。圆二色性和质谱研究均表明，Nα系列和Nε系列的树枝状聚合物在溶液中具有不同的构象及对模型磷脂的亲和力，这可能影响它们特定的杀微机制。
• Novel dendrimeric lipopeptides with antifungal activity
  作者：Jolanta Janiszewska、Marta Sowińska、Aleksandra Rajnisz、Jolanta Solecka、Izabela Łącka、Sławomir Milewski、Zofia Urbańczyk-Lipkowska

  DOI：10.1016/j.bmcl.2011.12.051

  日期：2012.2

  A series of new cationic lipopeptides containing branched, amphiphilic polar head derived from (Lys)Lys(Lys) dendron and C-8 or C-12 chain at C-end were designed, synthesized and characterized. Antimicrobial in vitro activity expressed as minimal inhibitory concentration (MIC) was evaluated against Gram-positive and Gram-negative bacteria and yeasts from the Candida genus. A significant enhancement of antimicrobial potency along with increased selectivity against Candida reference strains was detected for derivatives with the C12 residue. Several compounds were characterized by a low hemotoxicity. The antifungal activity of branched lipopeptides is multimodal and concentration dependent. Several compounds, studied in detail, induced potassium leakage from fungal cells, caused morphological alterations of fungal cells and inhibited activity of candidal beta(1,3)-glucan synthase. (C) 2011 Elsevier Ltd. All rights reserved.
• [EN] DENDRIMERIC COMPOUNDS COMPRISING AMINO ACIDS, HYPERBRANCHED CORE COMPOUND, PROCESS FOR PREPARATION OF DENDRIMERIC COMPOUNDS COMPRISING AMINO ACIDS AND HYPERBRANCHED CORE COMPOUND, AND USE THEREOF<br/>[FR] COMPOSÉS DENDRIMÉRIQUES COMPRENANT DES ACIDES AMINÉS, COMPOSÉ COEUR HYPERRAMIFIÉ, PROCÉDÉ DE PRÉPARATION DE COMPOSÉS DENDRIMÉRIQUES COMPRENANT DES ACIDES AMINÉS ET UN COMPOSÉ COEUR HYPERRAMIFIÉ, ET LEURS UTILISATIONS
  申请人：INST CHEMII ORGANICZNEJ POLSKA

  公开号：WO2010033043A8

  公开（公告）日：2010-05-14
• HYDROPHILIC SOMATOSTATIN ANALOGS
  申请人：THE ADMINISTRATORS OFTHE TULANE UNIVERSITY EDUCATIONAL FUND

  公开号：EP1131343A1

  公开（公告）日：2001-09-12