(2-azidoethyl)-2,2',2'',3,3',3'',4'',6,6',6''-deca-O-acetyl-β-D-maltotrioside | 1350829-28-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2-azidoethyl)-2,2',2'',3,3',3'',4'',6,6',6''-deca-O-acetyl-β-D-maltotrioside
• CAS: 1350829-28-5
• 化学式: C₄₀H₅₅N₃O₂₆
• 分子量: 993.881
• InChiKey: GPUBIHZMGVFDAF-GOJLZCMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.53
• 重原子数：
  69.0
• 可旋转键数：
  21.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  367.14
• 氢给体数：
  0.0
• 氢受体数：
  27.0

反应信息

• 作为反应物：
  描述：

  (2-azidoethyl)-2,2',2'',3,3',3'',4'',6,6',6''-deca-O-acetyl-β-D-maltotrioside 在 二碳酸二叔丁酯 、 5%-palladium/activated carbon 、 氢气 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 22.0h， 生成
  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
• 作为产物：
  描述：

  2-叠氮基乙醇 、 β-D-maltotriose undecaacetate 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以4.38 g的产率得到(2-azidoethyl)-2,2',2'',3,3',3'',4'',6,6',6''-deca-O-acetyl-β-D-maltotrioside
  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

文献信息

• Synthesis of Structurally Defined Nitroxide Spin-Labeled Glycolipids as Useful Probes for Electron Paramagnetic Resonance (EPR) Spectroscopy Studies of Cell Surface Glycans
  作者：Zhongwu Guo、Xin Yan

  DOI：10.1055/a-1768-2138

  日期：2022.6

  functionalized free glycans as the last synthetic step. These glycolipids are useful probes for the study of cell surface glycans by electron paramagnetic resonance spectroscopy. Moreover, the key synthetic intermediates, free glycolipids carrying a flexible azido group at the glycan non-reducing end, are widely useful platforms for accessing glycolipids with other molecular labels.

  设计了四种携带不同聚糖和在聚糖非还原端具有硝基氧自由基自旋的糖脂，并通过有效和简化的合成策略从游离葡萄糖和麦芽寡糖中合成。这种合成策略的主要特征包括游离碳水化合物的区域选择性功能化以及作为最后合成步骤的自由基自旋标记与功能化游离聚糖的偶联。这些糖脂是通过电子顺磁共振光谱研究细胞表面聚糖的有用探针。此外，关键的合成中间体，即在聚糖非还原端带有柔性叠氮基的游离糖脂，是获取具有其他分子标记的糖脂的广泛有用的平台。