磺基琥珀生物素 | 194041-65-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 生物素及其衍生物
• 中文名称: 磺基琥珀生物素
• 英文名称: sulfosuccinimidobiotin
• 英文别名: sulfo-NHS-biotin；sulfo-N-hydroxysuccinimidyl-biotin；sodium;(3aS,4S,6aR)-4-[5-(2,5-dioxo-3-sulfopyrrolidin-1-yl)oxy-5-oxopentyl]-3a,4,6,6a-tetrahydro-1H-thieno[3,4-d]imidazol-2-olate
• CAS: 194041-65-1
• 化学式: C₁₄H₁₈N₃O₈S₂*Na
• 分子量: 443.434
• InChiKey: DREOJRVDBCALEG-WCYHLEDJSA-M

物化性质

• 溶解度：
  DMF：30mg/mL； DMSO：20mg/mL； PBS（pH 7.2）：10 mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  -4.15
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  196
• 氢给体数：
  2
• 氢受体数：
  9

制备方法与用途

磺基NHS生物素（钠）能够强力标记单一SDS-2ME可溶性表皮蛋白[1]。

反应信息

• 作为反应物：
  描述：

  磺基琥珀生物素 、 盐酸多巴胺 在 potassium dihydrogenphosphate 作用下， 以 水 为溶剂， 反应 26.0h， 以40%的产率得到N-[2-(3,4-dihydroxyphenyl)ethyl]biotinamide
  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：

  N-hydroxysulfosuccinimide sodium salt 、 D-生物素 在 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 以47%的产率得到磺基琥珀生物素
  参考文献：
  名称：

  N-羟基硫代琥珀酰亚胺生物素酯及其衍生物的制备方法

  摘要：

  本发明提供一种N‑羟基硫代琥珀酰亚胺生物素酯及其衍生物的制备方法，包括如下步骤：步骤一：将生物素与N‑羟基琥珀酰亚胺磺酸或N‑羟基琥珀酰亚胺磺酸盐加入到第一溶剂中，在缩合剂的作用下发生缩合反应；步骤二：将步骤一反应后得到的反应液中的所述第一溶剂去除，剩余物用色谱进行分离，并收集含有N‑羟基硫代琥珀酰亚胺生物素酯或其衍生物的分离溶液；步骤三：去除所述分离溶液中的第二溶剂，得到N‑羟基硫代琥珀酰亚胺生物素酯或其衍生物。本发明的制备方法适合放大生产，原料易得，制备工艺简单，对环境友好，同时也避免了产物在后处理过程中变质分解的技术问题。

  公开号：

  CN107056802A

文献信息

• Synthesis of biotinylated muramyl tripeptides with NOD2-stimulating activity
  作者：Nicolas Gisch、Birte Buske、Holger Heine、Buko Lindner、Ulrich Zähringer

  DOI：10.1016/j.bmcl.2011.04.005

  日期：2011.6

  Muramyl di- and tri-peptides are putative activators of the innate immune system through stimulation of the NOD2 receptor. To provide tools for the clarification of the mechanism of this activation we isolated different UDP-muramyl tripeptides (Lys- and DAP-type) from bacteria and used them to synthesize biotinylated derivatives. All biotinylated compounds retained their ability to activate NOD2 in a cell-based test system and are therefore suitable for binding studies aimed at identifying the appropriate pattern recognition receptor(s). (C) 2011 Elsevier Ltd. All rights reserved.
• 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
  作者：Shin Aoki、Nanako Matsuo、Kengo Hanaya、Yasuyuki Yamada、Yoshiyuki Kageyama

  DOI：10.1016/j.bmc.2009.03.031

  日期：2009.5

  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.
• N-羟基硫代琥珀酰亚胺生物素酯及其衍生物的制备方法
  申请人：河北百灵威超精细材料有限公司

  公开号：CN107056802A

  公开（公告）日：2017-08-18

  本发明提供一种N‑羟基硫代琥珀酰亚胺生物素酯及其衍生物的制备方法，包括如下步骤：步骤一：将生物素与N‑羟基琥珀酰亚胺磺酸或N‑羟基琥珀酰亚胺磺酸盐加入到第一溶剂中，在缩合剂的作用下发生缩合反应；步骤二：将步骤一反应后得到的反应液中的所述第一溶剂去除，剩余物用色谱进行分离，并收集含有N‑羟基硫代琥珀酰亚胺生物素酯或其衍生物的分离溶液；步骤三：去除所述分离溶液中的第二溶剂，得到N‑羟基硫代琥珀酰亚胺生物素酯或其衍生物。本发明的制备方法适合放大生产，原料易得，制备工艺简单，对环境友好，同时也避免了产物在后处理过程中变质分解的技术问题。