(2S,3S,4S,5S,6R)-2-[2-[2-[2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]-6-(hydroxymethyl)oxane-3,4,5-triol | 1133959-62-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4S,5S,6R)-2-[2-[2-[2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 1133959-62-2
• 化学式: C₁₈H₃₅N₃O₁₁
• 分子量: 469.489
• InChiKey: CHQMPAGEGPXTCP-ZBRFXRBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  32
• 可旋转键数：
  20
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  160
• 氢给体数：
  4
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  (2R,3R,4S,5S,6S)-2-(acetoxymethyl)-6-((17-azido-3,6,9,12,15-pentaoxaheptadecyl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以48%的产率得到(2S,3S,4S,5S,6R)-2-[2-[2-[2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
  参考文献：
  名称：

  Biofunctionalization on Alkylated Silicon Substrate Surfaces via “Click” Chemistry

  摘要：

  Biofunctionalization of silicon substrates is important to the development of silicon-based biosensors and devices. Compared to conventional organosiloxane films on silicon oxide intermediate layers, organic monolayers directly bound to the nonoxidized silicon substrates via Si-C bonds enhance the sensitivity of detection and the stability against hydrolytic cleavage. Such monolayers presenting a high density of terminal alkynyl groups for bioconjugation via copper-catalyzed azide-alkyne 1,3-dipolar cycloaddition (CuAAC, a "click" reaction) were reported. However, yields of the CuAAC reactions on these monolayer platforms were low. Also, the nonspecific adsorption of proteins on the resultant surfaces remained a major obstacle for many potential biological applications. Herein, we report a new type of "clickable" monolayers grown by selective, photoactivated surface hydrosilylation of alpha,omega-alkenynes, where the alkynyl terminal is protected with a trimethylgermanyl (TMG) group, on hydrogen-terminated silicon substrates. The TMG groups on the film are readily removed in aqueous solutions in the presence of Cu(I). Significantly, the degermanylation and the subsequent CuAAC reaction with various azides could be combined into a single step in good yields. Thus, oligo(ethylene glycol) (OEG) with an azido tag was attached to the TMG-alkyne surfaces, leading to OEG-terminated surfaces that reduced the nonspecific adsorption of protein (fibrinogen) by >98%. The CuAAC reaction could be performed in microarray format to generate arrays of mannose and biotin with varied densities on the protein-resistant OEG background. We also demonstrated that the monolayer platform could be functionalized with mannose for highly specific capturing of living targets (EScherichia coli expressing fimbriae) onto the silicon substrates.

  DOI：

  10.1021/ja1025497

文献信息

• Biofunctionalization on Alkylated Silicon Substrate Surfaces via “Click” Chemistry
  作者：Guoting Qin、Catherine Santos、Wen Zhang、Yan Li、Amit Kumar、Uriel J. Erasquin、Kai Liu、Pavel Muradov、Barbara Wells Trautner、Chengzhi Cai

  DOI：10.1021/ja1025497

  日期：2010.11.24

  Biofunctionalization of silicon substrates is important to the development of silicon-based biosensors and devices. Compared to conventional organosiloxane films on silicon oxide intermediate layers, organic monolayers directly bound to the nonoxidized silicon substrates via Si-C bonds enhance the sensitivity of detection and the stability against hydrolytic cleavage. Such monolayers presenting a high density of terminal alkynyl groups for bioconjugation via copper-catalyzed azide-alkyne 1,3-dipolar cycloaddition (CuAAC, a "click" reaction) were reported. However, yields of the CuAAC reactions on these monolayer platforms were low. Also, the nonspecific adsorption of proteins on the resultant surfaces remained a major obstacle for many potential biological applications. Herein, we report a new type of "clickable" monolayers grown by selective, photoactivated surface hydrosilylation of alpha,omega-alkenynes, where the alkynyl terminal is protected with a trimethylgermanyl (TMG) group, on hydrogen-terminated silicon substrates. The TMG groups on the film are readily removed in aqueous solutions in the presence of Cu(I). Significantly, the degermanylation and the subsequent CuAAC reaction with various azides could be combined into a single step in good yields. Thus, oligo(ethylene glycol) (OEG) with an azido tag was attached to the TMG-alkyne surfaces, leading to OEG-terminated surfaces that reduced the nonspecific adsorption of protein (fibrinogen) by >98%. The CuAAC reaction could be performed in microarray format to generate arrays of mannose and biotin with varied densities on the protein-resistant OEG background. We also demonstrated that the monolayer platform could be functionalized with mannose for highly specific capturing of living targets (EScherichia coli expressing fimbriae) onto the silicon substrates.