N-(16-mercaptopalmitoyl)-2-aminoethyl-β-D-glucopyranoside | 1350829-18-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N-(16-mercaptopalmitoyl)-2-aminoethyl-β-D-glucopyranoside
• CAS: 1350829-18-3
• 化学式: C₂₄H₄₇NO₇S
• 分子量: 493.706
• InChiKey: RECAACLTLUTSGG-PFKOEMKTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.31
• 重原子数：
  33.0
• 可旋转键数：
  20.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  128.48
• 氢给体数：
  6.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  S-acetyl-N-(16-mercaptopalmitoyl)-2-aminoethyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以84%的产率得到N-(16-mercaptopalmitoyl)-2-aminoethyl-β-D-glucopyranoside
  参考文献：
  名称：

  Saccharide-Functionalized Alkanethiols for Fouling-Resistant Self-Assembled Monolayers: Synthesis, Monolayer Properties, and Antifouling Behavior

  摘要：

  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.

  DOI：

  10.1021/la202774e