N-(4-azidobenzyl)-N-(2-[3,4-bis(tert-butyldimethylsilyloxy)phenyl]ethyl)amine | 1162643-37-9

• 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: N-(4-azidobenzyl)-N-(2-[3,4-bis(tert-butyldimethylsilyloxy)phenyl]ethyl)amine
• CAS: 1162643-37-9
• 化学式: C₂₇H₄₄N₄O₂Si₂
• 分子量: 512.843
• InChiKey: XGYVIDHKNWFLIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.73
• 重原子数：
  35.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  79.25
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-炔丙基生物素酰胺 、 N-(4-azidobenzyl)-N-(2-[3,4-bis(tert-butyldimethylsilyloxy)phenyl]ethyl)amine 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 水 、 叔丁醇 为溶剂， 反应 48.0h， 以70%的产率得到4-(D-biotinylaminomethyl)-1-(4-[2-{3,4-bis(tert-butyldimethylsilyloxy)phenyl}ethylaminomethyl]phenyl)-1,2,3-triazole
  参考文献：
  名称：

  Design and synthesis of a photocleavable biotin-linker for the photoisolation of ligand–receptor complexes based on the photolysis of 8-quinolinyl sulfonates in aqueous solution

  摘要：

  The ability of avidin (Avn) to form strong complex with biotin (Btn) is frequently used in the detection and isolation of biomolecules in biochemical, analytical, and medicinal research. The fact that the binding is nealy irreversible, however, constitutes a drawback in term of the isolation and purification of intact biomolecules. We recently found that 8-quinolinyl esters of aromatic or aliphatic sulfonic acids undergo photolysis when irradiated at 300-330 nm in aqueous solution at neutral pH. In this work, a biotin-dopamine (BD) conjugate containing a photocleavable 8-quinolinyl benzenesulfonate (QB) linker, BDQB, was designed and synthesized for use in the efficient recovery of dopamine-protein (e.g., antibody) complexes from an Avn-Btn system. The complexation of BDQB with a primary anti-dopamine antibody (anti-dopamine IgG(1) from mouse) on an Avn-coated plate was confirmed by an enzyme-linked immunosorbent assay ( ELISA) utilizing a secondary antibody (anti-IgG(1) antibody) conjugated with horseradish peroxidase (HRP). Upon the photoirradiation (at 313 nm) of the BDQB-IgG(1) complex, the release of dopamine-IgG(1) complex was confirmed by ELISA. Characterization of the resulting photoreleased dopamine anti-dopamine IgG(1) complex was performed by SDS-PAGE and Western blot. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.03.031
• 作为产物：
  描述：

  1-叠氮基-4-(溴甲基)苯 、 2-(3,4-bis((tert-butyldimethylsilyl)oxy)phenyl)ethan-1-amine 在 四丁基碘化铵 、 caesium carbonate 作用下， 以 氯仿 、 乙腈 为溶剂， 反应 1.5h， 以48%的产率得到N-(4-azidobenzyl)-N-(2-[3,4-bis(tert-butyldimethylsilyloxy)phenyl]ethyl)amine
  参考文献：
  名称：

  Design and synthesis of a photocleavable biotin-linker for the photoisolation of ligand–receptor complexes based on the photolysis of 8-quinolinyl sulfonates in aqueous solution

  摘要：

  The ability of avidin (Avn) to form strong complex with biotin (Btn) is frequently used in the detection and isolation of biomolecules in biochemical, analytical, and medicinal research. The fact that the binding is nealy irreversible, however, constitutes a drawback in term of the isolation and purification of intact biomolecules. We recently found that 8-quinolinyl esters of aromatic or aliphatic sulfonic acids undergo photolysis when irradiated at 300-330 nm in aqueous solution at neutral pH. In this work, a biotin-dopamine (BD) conjugate containing a photocleavable 8-quinolinyl benzenesulfonate (QB) linker, BDQB, was designed and synthesized for use in the efficient recovery of dopamine-protein (e.g., antibody) complexes from an Avn-Btn system. The complexation of BDQB with a primary anti-dopamine antibody (anti-dopamine IgG(1) from mouse) on an Avn-coated plate was confirmed by an enzyme-linked immunosorbent assay ( ELISA) utilizing a secondary antibody (anti-IgG(1) antibody) conjugated with horseradish peroxidase (HRP). Upon the photoirradiation (at 313 nm) of the BDQB-IgG(1) complex, the release of dopamine-IgG(1) complex was confirmed by ELISA. Characterization of the resulting photoreleased dopamine anti-dopamine IgG(1) complex was performed by SDS-PAGE and Western blot. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.03.031

文献信息

• Design and Synthesis of Photocleavable Biotinylated-Dopamine with Polyethyleneoxy Photocleavable Linkers
  作者：Shin Aoki、Kengo Hanaya、Yoshiyuki Kageyama、Masanori Kitamura

  DOI：10.3987/com-10-s(e)124

  日期：——

  Previously, we reported the synthesis of a biotin dopamine conjugate (Btn-DA) with a photocleavable 8-quinolinyl benzenesulfonate (QB) linker for the isolation of an intact complex of DA and anti-DA antibody (IgG(1)) (DA-IgG(1) complex). In this work, we synthesized a photocleavable Btn-DA conjugate with a polyethyleneoxy linker to improve the complexation efficiency and the recovery yields of DA-IgG(1) complex. The results of QCM, ELISA, and Western blot analyses indicate that the introduction of polyethyleneoxy linkers improved the efficiency of DA-IgG(1) complexation.