(2-{2-[2-(11-Acetylsulfanyl-undecyloxy)-ethoxy]-ethoxy}-ethoxy)-acetic acid | 716339-45-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硫代羧酸及其衍生物
• 英文名称: (2-{2-[2-(11-Acetylsulfanyl-undecyloxy)-ethoxy]-ethoxy}-ethoxy)-acetic acid
• CAS: 716339-45-6
• 化学式: C₂₁H₄₀O₇S
• 分子量: 436.61
• InChiKey: RLWDJGOFEUCIMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.93
• 重原子数：
  29.0
• 可旋转键数：
  23.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  91.29
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (2-{2-[2-(11-Acetylsulfanyl-undecyloxy)-ethoxy]-ethoxy}-ethoxy)-acetic acid 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以70%的产率得到23-mercapto-3,6,9,12-tetraoxatricosanoic acid
  参考文献：
  名称：

  Grafting Nitrilotriacetic Groups onto Carboxylic Acid-Terminated Self-Assembled Monolayers on Gold Surfaces for Immobilization of Histidine-Tagged Proteins

  摘要：

  In this paper, we report a common intermediate method to present nitrilotriacetic acid (NTA) groups on gold surfaces for immobilizing His-tagged proteins onto the surfaces, and a full characterization of self-assembled monolayers (SAMs) terminating in carboxylic acids [HS(CH2)(15)COOH (C15-COOH), HS(CH2)(11)(OCH2CH2)(3)-OCH2COOH (EG3-COOH), and HS(CH2)(11)(OCH2CH2)(5)OCH2COOH (EG5-COOH)] and coupling reactions of an NTA-containing primary amine [(1S)-N-(5-amino-l-carboxypentyl)iminodiacetic acid; NTA-NH2] with the carboxylic acid on surfaces. The lateral packing densities of the COOH-terminated SAMs were calculated to be 4.32 (for C15-COOH), 3.49 (for EG3-COOH), and 2.65 (for EG5-COOH) molecules/nm(2). The packing densities were decreased by incorporating a relatively flexible ethylene glycol (EG) group into the backbone of alkanethiols and increasing the number of the EG groups in the backbone of alkanethiols. The NTA group was then attached by coupling NTA-NH2 with the COOH group on the surfaces, followed by a Ni(II) complexation. The coupling reaction was characterized by FT-IR spectroscopy, ellipsometry, and XPS, and the coupling efficiency ("yield") was estimated by comparing the experimentally determined N 1s to S 2p (N/S) ratio of XPS data with the N/S ratio calculated for the functionalization of the SAMs presenting NTANi(II): the coupling yields were 30% (for C15-COOH) and 25% (for EG3-COOH and EG5-COOH). Preliminary experiments on the binding of His-tagged proteins onto the surfaces were also performed.

  DOI：

  10.1021/jp0378236
• 作为产物：
  描述：

  3,6,9,12-Tetraoxatricos-22-enoic acid, 1,1-dimethylethyl ester 在 4,4'-偶氮双(4-氰基戊酸) 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 13.0h， 生成 (2-{2-[2-(11-Acetylsulfanyl-undecyloxy)-ethoxy]-ethoxy}-ethoxy)-acetic acid
  参考文献：
  名称：

  Grafting Nitrilotriacetic Groups onto Carboxylic Acid-Terminated Self-Assembled Monolayers on Gold Surfaces for Immobilization of Histidine-Tagged Proteins

  摘要：

  In this paper, we report a common intermediate method to present nitrilotriacetic acid (NTA) groups on gold surfaces for immobilizing His-tagged proteins onto the surfaces, and a full characterization of self-assembled monolayers (SAMs) terminating in carboxylic acids [HS(CH2)(15)COOH (C15-COOH), HS(CH2)(11)(OCH2CH2)(3)-OCH2COOH (EG3-COOH), and HS(CH2)(11)(OCH2CH2)(5)OCH2COOH (EG5-COOH)] and coupling reactions of an NTA-containing primary amine [(1S)-N-(5-amino-l-carboxypentyl)iminodiacetic acid; NTA-NH2] with the carboxylic acid on surfaces. The lateral packing densities of the COOH-terminated SAMs were calculated to be 4.32 (for C15-COOH), 3.49 (for EG3-COOH), and 2.65 (for EG5-COOH) molecules/nm(2). The packing densities were decreased by incorporating a relatively flexible ethylene glycol (EG) group into the backbone of alkanethiols and increasing the number of the EG groups in the backbone of alkanethiols. The NTA group was then attached by coupling NTA-NH2 with the COOH group on the surfaces, followed by a Ni(II) complexation. The coupling reaction was characterized by FT-IR spectroscopy, ellipsometry, and XPS, and the coupling efficiency ("yield") was estimated by comparing the experimentally determined N 1s to S 2p (N/S) ratio of XPS data with the N/S ratio calculated for the functionalization of the SAMs presenting NTANi(II): the coupling yields were 30% (for C15-COOH) and 25% (for EG3-COOH and EG5-COOH). Preliminary experiments on the binding of His-tagged proteins onto the surfaces were also performed.

  DOI：

  10.1021/jp0378236

文献信息

• Multimerization of DAB-1 onto Au GNPs affords new potent and selective <i>N</i>-acetylgalactosamine-6-sulfatase (GALNS) inhibitors
  作者：C. Matassini、C. Vanni、A. Goti、A. Morrone、M. Marradi、F. Cardona

  DOI：10.1039/c8ob02587h

  日期：——

  Gold glyconanoparticles (Au GNPs) decorated with the natural iminosugar DAB-1 at different densities are reported.

  本研究报道了用不同密度的天然亚氨基糖 DAB-1 装饰的金甘康颗粒（Au GNPs）。
• Hybrid Multivalent Jack Bean α-Mannosidase Inhibitors: The First Example of Gold Nanoparticles Decorated with Deoxynojirimycin Inhitopes
  作者：Costanza Vanni、Anne Bodlenner、Marco Marradi、Jérémy P. Schneider、Maria de los Angeles Ramirez、Sergio Moya、Andrea Goti、Francesca Cardona、Philippe Compain、Camilla Matassini

  DOI：10.3390/molecules26195864

  日期：——

  responsiveness to the multivalent presentation of iminosugar inhitopes. We report, in this work, the preparation of water dispersible gold nanoparticles simultaneously coated with the iminosugar deoxynojirimycin (DNJ) inhitope and simple monosaccharides (β-d-gluco- or α-d-mannosides). The display of DNJ at the gold surface has been modulated (i) by using an amphiphilic linker longer than the aliphatic

  在碳水化合物加工酶中，杰克豆 α-甘露糖苷酶 (JBα-man) 是对亚氨基糖 inhitopes 的多价呈递反应最好的糖苷酶。在这项工作中，我们报告了同时包被亚氨基糖脱氧野尻霉素 (DNJ) inhitope 和简单单糖（β-d-gluco- 或 α-d-mannosides）的水分散性金纳米粒子的制备。DNJ 在金表面的展示已被调节 (i) 通过使用比用于单糖的脂肪链更长的两亲性接头和 (ii) 通过呈现 inhitope，不仅以单体形式，而且以三聚体方式通过树突方法与糖纳米技术的结合。后一种策略导致对 JBα-man 的抑制活性的强烈增强，K i在纳摩尔范围内 ( K i = 84 nM)，即比单价参考化合物高三个数量级以上。