[2-(2-{2-[2-(11-mercapto-undecyloxy)ethoxy]ethoxy}ethoxy)ethoxy]acetic acid | 552855-26-2

• 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: [2-(2-{2-[2-(11-mercapto-undecyloxy)ethoxy]ethoxy}ethoxy)ethoxy]acetic acid
• 英文别名: 26-Sulfanyl-3,6,9,12,15-pentaoxahexacosan-1-oic acid；2-[2-[2-[2-[2-(11-sulfanylundecoxy)ethoxy]ethoxy]ethoxy]ethoxy]acetic acid
• CAS: 552855-26-2
• 化学式: C₂₁H₄₂O₇S
• 分子量: 438.626
• InChiKey: ZICSAEOXPVFWRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  29
• 可旋转键数：
  25
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  84.4
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-羟基丁二酰亚胺 、 [2-(2-{2-[2-(11-mercapto-undecyloxy)ethoxy]ethoxy}ethoxy)ethoxy]acetic acid 在 N,N'-二环己基碳二亚胺 作用下， 生成
  参考文献：
  名称：

  铁蛋白纳米笼的引导组装：单分散纳米元素的高度有序的阵列。

  摘要：

  高密度排列的高度有序的铁蛋白纳米笼是通过将硫醇修饰的铁蛋白引导组装在预先构图的金纳米点上而制成的，这些金点通过嵌段共聚物胶束光刻技术制备。如通过扫描电子和扫描力显微镜所证实的，将一个且仅有一个铁蛋白纳米笼固定在每个金纳米点上。

  DOI：

  10.1002/adma.200903578
• 作为产物：
  描述：

  [2-(2-{2-[2-(11-acetylsulfanyl-undecyloxy)ethoxy]ethoxy}ethoxy)ethoxy]acetic acid ethyl ester 在 lithium hydroxide 作用下， 以 甲醇 为溶剂， 生成 [2-(2-{2-[2-(11-mercapto-undecyloxy)ethoxy]ethoxy}ethoxy)ethoxy]acetic acid
  参考文献：
  名称：

  硫醇配体介导的块状硫剥离为纳米片和纳米点：在抗菌活性中的应用

  摘要：

  将块状材料减少为层或点会导致其物理化学和光电特性发生深刻变化，从而产生从设备制造到生物医学的广泛应用。在这方面，硫纳米材料的制备由于其低毒性而引起了人们的广泛关注。传统的硫纳米材料合成方法通常涉及苛刻的反应条件，这为创建纳米材料（例如纳米片（NS）和纳米点（ND））的便捷方法留下了空白。本文报道了使用表面活性剂硫醇配体和探针超声处理对大量硫进行机械剥离，这对现有方法做出了独特的贡献。在报道的方法中，硫醇基团与硫表面结合，促进剥离和稳定，而亲水端为剥离的纳米材料提供官能团。剥离可以产生纳米片或纳米点，具体取决于硫醇配体和剥离时间。这种方法提供了使用生物活性硫醇配体剥落大量硫的机会。考虑到这一目标，使用 4-巯基苯硼酸 (BA) 剥落大量硫以靶向革兰氏阳性菌。这种使用硫醇配体的块状硫的创新剥离策略为合成具有广泛应用的功能化硫纳米材料带来了巨大的希望，特别是在生物医学领域。

  DOI：

  10.1039/d3tb02403b

文献信息

• Ligand Conjugation of Chemically Exfoliated MoS₂
  作者：Stanley S. Chou、Mrinmoy De、Jaemyung Kim、Segi Byun、Conner Dykstra、Jin Yu、Jiaxing Huang、Vinayak P. Dravid

  DOI：10.1021/ja310929s

  日期：2013.3.27

  MoS2 is a two-dimensional material that is gaining prominence due to its unique electronic and chemical properties. Here, we demonstrate ligand conjugation of chemically exfoliated MoS2 using thiol chemistry. With this method, we modulate the ζ-potential and colloidal stability of MoS2 sheets through ligand designs, thus enabling its usage as a selective artificial protein receptor for β-galactosidase

  MoS2 是一种二维材料，由于其独特的电子和化学性质而越来越受到重视。在这里，我们使用硫醇化学证明了化学剥离的 MoS2 的配体共轭。使用这种方法，我们通过配体设计调节 MoS2 片层的 ζ 电位和胶体稳定性，从而使其能够用作 β-半乳糖苷酶的选择性人工蛋白质受体。简便的硫醇官能化路线为可溶液加工的 MoS2 片材的表面改性打开了大门。
• Arrays for the Combinatorial Exploration of Cell Adhesion
  作者：Brendan P. Orner、Ratmir Derda、Rachel L. Lewis、James A. Thomson、Laura L. Kiessling

  DOI：10.1021/ja0474291

  日期：2004.9.1

  A new method for the fabrication of arrays of self-assembled monolayers (SAMs) of alkane thiols (ATs) on gold to combinatorially assay surfaces for cell adhesion is reported. A fluorous SAM, which is both cytophobic and solvophobic, was used as the background between the array features. The resulting solvophobic background permits the application of an assembly after conjugation strategy for fabrication. SAMs containing mixtures of ATs and peptide-terminated ATs were generated. Multiple cell types demonstrated differential and specific binding to these surfaces. Additionally, pluripotent human embryonic stem cells proliferated on surfaces generated by this method.
• Control of Protein Structure and Function through Surface Recognition by Tailored Nanoparticle Scaffolds
  作者：Rui Hong、Nicholas O. Fischer、Ayush Verma、Catherine M. Goodman、Todd Emrick、Vincent M. Rotello

  DOI：10.1021/ja037470o

  日期：2004.1.28

  Thioalkyl and thioalkylated oligo(ethylene glycol) (OEG) ligands with chain-end functionality were used to fabricate water-soluble CdSe nanoparticle scaffolds. Surface recognition of chymotrypsin (ChT) was achieved using these functionalized nanoparticle scaffolds, with three levels of interaction demonstrated: no interaction (OEG terminated with hydroxyl group), inhibition with denaturation (carboxylate-terminated thioalkyl ligands), and inhibition with retention of structure (carboxylate-terminated OEG). The latter process was reversible upon an increase in ionic strength, with essentially complete restoration of enzymatic activity.
• Defined surfaces of self-assembled monolayers and stem cells
  申请人：Kiessling L. Laura

  公开号：US20070207543A1

  公开（公告）日：2007-09-06

  A method for the construction of arrays from self-assembling monolayers is described. The arrays have particular utility for the screening of peptides ligands that can foster the growth of cells in culture. This technique has been used to identify peptide ligands that foster the growth of human stem cells, which otherwise require an extracellular matrix in order to grow in an undifferentiated state. This also makes possible an assay to identify other such peptides.
• Small Water-soluble Quantum Dots
  申请人：THE BOARD OF TRUSTEES OF THE UNIVERSITY OF ILLINOIS

  公开号：US20150236220A1

  公开（公告）日：2015-08-20

  Water-soluble, stable fluorescent PEGylated alkanethiol-coated quantum dots are made by contacting quantum dots with PEGylated alkanethiol in a non-oxidative, water-immiscible organic reaction solvent under a non-oxidative gas, wherein the reaction solvent is in contact with an aqueous phase, at elevated temperature and time sufficient to coat the dots with the PEGylated alkanethiol, wherein resultant water-soluble, stable fluorescent PEGylated alkanethiol-coated dots enter the aqueous phase.