16-hydroxyhexadecyl 4-methylbenzenesulfonate | 211869-81-7

• 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: 16-hydroxyhexadecyl 4-methylbenzenesulfonate
• 英文别名: 16-(p-Toluensulfonyloxy)hexadecanol
• CAS: 211869-81-7
• 化学式: C₂₃H₄₀O₄S
• 分子量: 412.634
• InChiKey: AEAWVGQPVHLAPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  28
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  72
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  16-hydroxyhexadecyl 4-methylbenzenesulfonate 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 Acetic acid (2R,3R,4S,5S,6R)-3-acetoxy-6-acetoxymethyl-5-((2S,3R,4R,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-2-(16-thiocyanato-hexadecyloxy)-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  The synthesis of 16-mercaptohexadecanyl glycosides for biosensor applications

  摘要：

  The P-k trisaccharide and the central disaccharide element of asialo GM(1) activated as their trichloroacetimidates were each used to glycosylate 16-(p-toluensulfonyloxy)hexadecanol 1. Displacement of the tosyl group by thiocyanate followed by sodium borohydride reduction and saponification afforded oligosaccharide 16-mercaptohexadecanyl glycosides that were isolated as the corresponding disulfides 6 and 17 unless oxygen was rigorously excluded from the solvents used for work-up. Dithiothreitol reduction of disulfides and subsequent isolation under an inert atmosphere with degassed solvents gave the thiols 7 and 18. Chemisorption of omega-glycosyl alkanethiols and alkanethiols onto gold electrodes produces self-assembled monolayers that can act as amperometric biosensors for the detection of proteins that bind to the immobilized oligosaccharide epitope. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00053-6
• 作为产物：
  描述：

  1,16-十六烷二醇 、 对甲苯磺酰氯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.0h， 以52%的产率得到16-hydroxyhexadecyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  结构异构定向杯[6]芳烃基轮烷的合成与表征

  摘要：

  合成了由三(N-苯基脲基)杯[6]芳烃轮1和N,N'-二烷基紫精基轴组成的定向轮烷，其中轮上、下轮缘的二苯乙酰塞与双吡啶之间的跨距轴向分量的阳离子部分长度不同。遵循顺序合成途径以实现定向异构体的选择性形成，其中轴的短（或长）链位于车轮的上轮辋或下轮辋上。所采用的合成策略涉及轴 2a-c 的上边缘螺纹以产生定向的假轮烷，然后原位塞住。通过详细的核磁共振实验揭示了定向轮烷的结构，并通过紫外/可见光、循环伏安法、和 EPR 测量。将结果与其对称对应物的结果进行比较。

  DOI：

  10.1002/ejoc.201501522

文献信息

• Card-based biosensor device
  申请人：Helix BioPharma Corporation

  公开号：US06300141B1

  公开（公告）日：2001-10-09

  A diagnostic card device for use in detecting or quantitating an analyte present in a liquid sample, comprising a card substrate having a sample introduction region, a biosensor, and a sample-flow pathway communicating between the sample-introduction region and the biosensor, circuitry for generating an analyte-dependent electrical signal from the biosensor; and a signal-responsive element for recording such signal. In one embodiment, the biosensor includes a detection surface with surface-bound molecules of a first charged, coil-forming peptide capable of interacting with a second, oppositely charged coil-forming peptide to form a stable &agr;-helical coiled-coil heterodimer, where the binding of the second peptide to the first peptide, to form such heterodimer, is effective to measurably alter a signal generated by the biosensor. The sample-flow pathway contains diffusibly bound conjugate of the second coil-forming peptide and the analyte (or an analyte analog) and immobilized analyte-binding agent. The analyte in the liquid sample and the conjugate compete for binding with the immobilized analyte-binding agent. Unbound conjugate migrates by capillarity to the biosensor. Liquid sample containing conjugate migrates in the sample flow pathway by capillary action or is driven by a micro-pump. In another embodiment, the biosensor includes an electrode substrate coated with a high-dielectric hydrocarbon-chain monolayer, and having analyte-binding agent attached to the exposed monolayer surface. Binding of analyte to the monolayer-bound analyte-binding agent, and the resultant perturbation of the monolayer structure, causes ion-mediated electron flow across the monolayer.

  一种用于检测或定量液体样品中存在的分析物的诊断卡设备，包括具有样品引入区域、生物传感器和样品流通路径的卡基底，该路径在样品引入区域和生物传感器之间通信，电路用于从生物传感器产生分析物依赖的电信号；以及用于记录这种信号的信号响应元件。在一种实施例中，生物传感器包括具有第一带电、成螺旋肽的检测表面，该肽能够与第二相反带电的成螺旋肽相互作用，形成稳定的α-螺旋螺旋卷曲异二聚体，其中第二肽与第一肽结合形成这样的异二聚体，有效地改变了生物传感器产生的信号。样品流动路径包含第二卷曲形成肽和分析物（或分析物类似物）的可扩散结合物以及固定的分析物结合剂。液体样品中的分析物和结合物与固定的分析物结合剂竞争结合。未结合的结合物通过毛细作用迁移到生物传感器。含结合物的液体样品通过毛细作用在样品流动路径中迁移或被微泵驱动。在另一种实施例中，生物传感器包括涂有高介电烃链单层的电极基底，并具有附着在暴露的单层表面上的分析物结合剂。分析物与单层结合的分析物结合剂的结合以及由此引起的单层结构扰动导致离子介导的电子流通过单层。
• Biosensor device and method
  申请人：McGill University

  公开号：US06107080A1

  公开（公告）日：2000-08-22

  A biosensor apparatus for detecting a binding event between a ligand and receptor. The apparatus includes an electrode substrate coated with a high-dielectric hydrocarbon-chain monolayer, and having ligands attached to the exposed monolayer surface. Binding of a receptor to the monolayer-bound ligand, and the resultant perturbation of the monolayer structure, causes ion-mediated electron flow across the monolayer. In one embodiment, the monolayers have a coil-coil heterodimer embedded therein, one subunit of which is attached to the substrate, and the second of which carries the ligand at the monolayer surface.

  一种生物传感器装置，用于检测配体和受体之间的结合事件。该装置包括涂有高介电碳氢链单层的电极基底，并在暴露的单层表面上附着配体。受体与单层结合的配体，并且单层结构的结果扰动导致离子介导的电子流穿过单层。在一种实施例中，单层中嵌入了一个卷曲异二聚体，其中一个亚基附着在基底上，第二个亚基携带单层表面的配体。
• A homologous series of permanently charged 1,4-dihydropyridines: novel probes designed to localize drug binding sites on ion channels
  作者：Nandkishore Baindur、Aleta Rutledge、David J. Triggle

  DOI：10.1021/jm00075a034

  日期：1993.11
• BIOSENSOR DEVICE AND METHOD
  申请人：Pence, Inc.

  公开号：EP1005644B1

  公开（公告）日：2003-03-12
• US5955379A
  申请人：——

  公开号：US5955379A

  公开（公告）日：1999-09-21