N-(S-acetyl-16-mercaptohexadecanoyloxy)-succinimide | 221623-50-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: N-(S-acetyl-16-mercaptohexadecanoyloxy)-succinimide
• 英文别名: N-(S-acetyl-16-mercaptohexadecanoyloxy)succinimide；(2,5-Dioxopyrrolidin-1-yl) 16-acetylsulfanylhexadecanoate
• CAS: 221623-50-3
• 化学式: C₂₂H₃₇NO₅S
• 分子量: 427.605
• InChiKey: BABLUCVCXKORFW-UHFFFAOYSA-N

物化性质

• 沸点：
  527.4±42.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  29
• 可旋转键数：
  19
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(S-acetyl-16-mercaptohexadecanoyloxy)-succinimide 在 乙酸肼 、 碳酸氢钠 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 50.0h， 生成 N-[N_α,N_α-bis(carboxymethyl)-L-lysine]-16-mercaptohexadecanamide
  参考文献：
  名称：

  Nitrilotriacetic Acid-Modified Magnetic Nanoparticles as a General Agent to Bind Histidine-Tagged Proteins

  摘要：

  Using Nalpha,Nalpha-bis(carboxymethyl)lysine to react with FePt magnetic nanoparticles, we synthesized the FePt-NTA conjugate, which immobilizes Ni2+ ions and selectively binds to histidine-tagged proteins at concentration as low as 0.5 pM. This simple system serves as a useful alternative to existing protocols for protein separation and also acts as a versatile agent for transporting and anchoring proteins.

  DOI：

  10.1021/ja031776d
• 作为产物：
  描述：

  16-羟基棕榈酸 在 氢溴酸 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 二氯甲烷 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 99.0h， 生成 N-(S-acetyl-16-mercaptohexadecanoyloxy)-succinimide
  参考文献：
  名称：

  适用于与金和氨基官能化表面缀合的糖鞘脂和甘油脂的类似物

  摘要：

  描述了天然脂类似物（即乳糖基神经酰胺，globoriasyl神经酰胺和磷脂酰胆碱）的类似物的一般合成，其中烷基链之一带有末端硫醇或羧基官能团。通过鞘氨醇或单酰基甘油衍生物的N-或O-酰化制备脂质。这些脂质适用于锚定在金或氨基官能化的表面，从而形成细胞膜的模拟物，用于研究蛋白质与碳水化合物的相互作用。

  DOI：

  10.1016/s0040-4020(00)00946-7

文献信息

• Heterodimers of Nanoparticles:  Formation at a Liquid−Liquid Interface and Particle-Specific Surface Modification by Functional Molecules
  作者：Hongwei Gu、Zhimou Yang、Jinhao Gao、C. K. Chang、Bing Xu

  DOI：10.1021/ja045220h

  日期：2005.1.1

  On the basis of a fundamental property of nanoparticles, the self-assembling at a liquid-liquid interface to form "colloidosomes", a heterogeneous reaction takes place on the exposed surface of the nanoparticles to produce the heterodimers of two distinct nanospheres, which can be modified by two different functional molecules in a particle-specific manner.

  基于纳米粒子的一个基本特性，即在液-液界面自组装形成“胶体”，纳米粒子的暴露表面发生异质反应，产生两个不同纳米球的异二聚体，可以是由两种不同的功能分子以特定于颗粒的方式修饰。
• Controlled stoichiometric synthesis of DNA–quantum dot conjugates using Ni-mediated coordination chemistry
  作者：Haejin Kwon、Sukmin Hong、Heeyeon Kim、Youngseon Choi、Jaeseung Kim、Rita Song

  DOI：10.1039/c0cc03462b

  日期：——

  An oligonucleotide modified with Ni-nitrilotriacetate (NTA) was successfully synthesized and used for the stoichiometric functionalization of QDs. This synthetic approach allowed for the facile preparation of DNA–QD conjugates with a defined DNA/QD ratio using well-known Ni–histidine coordination chemistry. A FRET based DNA–QD nanoprobe was prepared using this method highlighting the great potential of this synthetic strategy.

  一种用镍-三乙酸（NTA）修饰的寡核苷酸被成功合成，并用于量子点的化学计量功能化。这种合成方法利用众所周知的镍-组氨酸配位化学，可以轻松制备具有特定DNA/QD比的DNA-QD共轭物。使用这种方法制备了一种基于荧光共振能量转移（FRET）的DNA-QD纳米探针，凸显了这种合成策略的巨大潜力。
• ω-Mercapto analogs of naturally occurring lipids
  作者：Jörgen Ohlsson、Göran Magnusson

  DOI：10.1016/s0040-4039(99)00104-5

  日期：1999.3

  Analogs of natural lipids, where one of the alkyl chains carries a terminal thiol functionality, were prepared by N- or O-acylation of sphingosine or monoacylglycerol derivatives, respectively, thus creating lipid mimics suitable for anchoring to e.g. gold surfaces.

  分别通过鞘氨醇或单酰基甘油衍生物的N-或O-酰化反应制备了其中一个烷基链带有末端硫醇官能度的天然脂质类似物，从而产生了适合锚定于例如金表面的脂质模拟物。
• <i>S</i>-Linked Ganglioside Analogues for Use in Conjugate Vaccines
  作者：Jamie R. Rich、David R. Bundle

  DOI：10.1021/ol036460p

  日期：2004.3.1

  Glycosidase resistant thioglycoside precursors of the melanoma-associated ganglioside GM(2) have been synthesized starting from lactose. Syntheses of several analogues of ganglioside GM(3) and a positional isomer have been developed. These compounds contain thio-linked sialic acid residues and a modified ceramide aglycon functionalized for coupling to proteins, surfaces, or matrices. The hydrolytic stability of these oligosaccharides enhances the immunogenicity of the corresponding conjugate vaccines by ensuring their integrity in the acidic compartments of antigen processing cells.
• Saccharide-Functionalized Alkanethiols for Fouling-Resistant Self-Assembled Monolayers: Synthesis, Monolayer Properties, and Antifouling Behavior
  作者：Timmy Fyrner、Hung-Hsun Lee、Alberto Mangone、Tobias Ekblad、Michala E. Pettitt、Maureen E. Callow、James A. Callow、Sheelagh L. Conlan、Robert Mutton、Anthony S. Clare、Peter Konradsson、Bo Liedberg、Thomas Ederth

  DOI：10.1021/la202774e

  日期：2011.12.20

  We describe the synthesis of a series of mono-, di-, and trisaccharide-functionalized alkanethiols as well as the formation of fouling-resistant self-assembled monolayers (SAMs) from these. The SAls,,Is were characterized using ellipsometry, wetting measurements, and infrared reflection absorption spectroscopy (WAS). We show that the structure of the carbohydrate moiety affects the packing density and that this also alters the alkane chain organization. Upon increasing the size of the sugar moieties (from mono- to di- and trisaccharides), the structural qualities of the monolayers deteriorated with increasing disorder, and for the trisaccharide, slow reorganization dynamics in response to changes in the environmental polarity were observed. The antifouling properties of these SAMs were investigated through protein adsorption experiments from buffer solutions as well as settlement (attachment) tests using two common marine fouling species, zoospores of the green macroalga Ulva linza and cypris larvae of the barnacle Balanus amphitrite. The SAMs showed overall good resistance to fouling by both the proteins and the tested marine organisms. To improve the packing density of the SAMs with bulky headgroups, we employed mixed SAMs where the saccharide-thiols are diluted with a filler molecule having a small 2-hydroxyethyl headgroup. This method also provides a means by which the steric availability of sugar moieties can be varied, which is of interest for specific interaction studies with surface-bound sugars. The results of the surface dilution study and the low nonspecific adsorption onto the SAMs both indicate the feasibility of this approach.