6-Vinylbenzo[c][1,2]oxaborol-1(3h)-ol | 1268336-34-0

• 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: 6-Vinylbenzo[c][1,2]oxaborol-1(3h)-ol
• 英文别名: 6-ethenyl-1-hydroxy-3H-2,1-benzoxaborole
• CAS: 1268336-34-0
• 化学式: C₉H₉BO₂
• 分子量: 159.98
• InChiKey: QTAQWOPUMRETST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.55
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-Vinylbenzo[c][1,2]oxaborol-1(3h)-ol 、 2-[十二烷硫基(硫代羰基)硫基]-2-甲基丙酸 在 NCC(CH₃)2NNC(CH₃)2CN 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  Monosaccharide-Responsive Release of Insulin from Polymersomes of Polyboroxole Block Copolymers at Neutral pH

  摘要：

  We synthesized a boroxole-containing styrenic monomer that can be polymerized by the reversible addition fragmentation and chain transfer (RAFT) method. Poly(styreneboroxole) (PBOx) and its block copolymers with a poly(ethylene glycol) (PEG) as a hydrophilic block displayed binding to monosaccharides in phosphate buffer at neutral pH, as quantified by Wang's competitive binding experiments. By virtue of a controlled radical polymerization, we were able to adjust the degree of polymerization of the PBOx block to yield sugar-responsive block copolymers that self-assembled into a variety of nanostructures including spherical and cylindrical micelles and polymer vesicles (polymersomes). Polymersomes of these block copolymers exhibited monosaccharide-responsive disassembly in a neutral-pH medium. We demonstrated the possibility of using these polymersomes as sugar-responsive delivery vehicles for insulin in neutral phosphate buffer (pH 7.4). Encapsulated insulin could be released from the polymersomes only in the presence of sugars under physiologically relevant pH conditions.

  DOI：

  10.1021/ja211728x
• 作为产物：
  描述：

  3-bromo-4-((methoxymethoxy)methyl)styrene 在 盐酸 、 magnesium 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 8.0h， 生成 6-Vinylbenzo[c][1,2]oxaborol-1(3h)-ol
  参考文献：
  名称：

  Monosaccharide-Responsive Release of Insulin from Polymersomes of Polyboroxole Block Copolymers at Neutral pH

  摘要：

  We synthesized a boroxole-containing styrenic monomer that can be polymerized by the reversible addition fragmentation and chain transfer (RAFT) method. Poly(styreneboroxole) (PBOx) and its block copolymers with a poly(ethylene glycol) (PEG) as a hydrophilic block displayed binding to monosaccharides in phosphate buffer at neutral pH, as quantified by Wang's competitive binding experiments. By virtue of a controlled radical polymerization, we were able to adjust the degree of polymerization of the PBOx block to yield sugar-responsive block copolymers that self-assembled into a variety of nanostructures including spherical and cylindrical micelles and polymer vesicles (polymersomes). Polymersomes of these block copolymers exhibited monosaccharide-responsive disassembly in a neutral-pH medium. We demonstrated the possibility of using these polymersomes as sugar-responsive delivery vehicles for insulin in neutral phosphate buffer (pH 7.4). Encapsulated insulin could be released from the polymersomes only in the presence of sugars under physiologically relevant pH conditions.

  DOI：

  10.1021/ja211728x

文献信息

• A General Method for Selective Recognition of Monosaccharides and Oligosaccharides in Water
  作者：Roshan W. Gunasekara、Yan Zhao

  DOI：10.1021/jacs.6b10773

  日期：2017.1.18

  Molecular recognition of carbohydrates plays vital roles in biology but has been difficult to achieve with synthetic receptors. Through covalent imprinting of carbohydrates in boroxole-functionalized cross-linked micelles, we prepared nanoparticle receptors for a wide variety of mono- and oligosaccharides. The boroxole functional monomer bound the sugar templates through cis-1,2-diol, cis-3,4-diol

  碳水化合物的分子识别在生物学中起着至关重要的作用，但很难通过合成受体实现。通过硼烷官能化交联胶束中碳水化合物的共价印记，我们制备了多种单糖和寡糖的纳米颗粒受体。硼烷功能单体通过 cis-1,2-diol、cis-3,4-diol 和 trans-4,6-diol 结合糖模板。蛋白质大小的纳米粒子对水中的 d-己醛糖显示出优异的选择性，具有亚毫摩尔级的结合亲和力，并完全区分了三种生物学上重要的己糖（葡萄糖、甘露糖和半乳糖）。由于增强的疏水相互作用，具有非极性苷元的糖苷显示出更强的结合。寡糖的区别在于它们的单糖结构单元，
• Monosaccharide-Responsive Release of Insulin from Polymersomes of Polyboroxole Block Copolymers at Neutral pH
  作者：Hyunkyu Kim、Young Ji Kang、Sebyung Kang、Kyoung Taek Kim

  DOI：10.1021/ja211728x

  日期：2012.3.7

  We synthesized a boroxole-containing styrenic monomer that can be polymerized by the reversible addition fragmentation and chain transfer (RAFT) method. Poly(styreneboroxole) (PBOx) and its block copolymers with a poly(ethylene glycol) (PEG) as a hydrophilic block displayed binding to monosaccharides in phosphate buffer at neutral pH, as quantified by Wang's competitive binding experiments. By virtue of a controlled radical polymerization, we were able to adjust the degree of polymerization of the PBOx block to yield sugar-responsive block copolymers that self-assembled into a variety of nanostructures including spherical and cylindrical micelles and polymer vesicles (polymersomes). Polymersomes of these block copolymers exhibited monosaccharide-responsive disassembly in a neutral-pH medium. We demonstrated the possibility of using these polymersomes as sugar-responsive delivery vehicles for insulin in neutral phosphate buffer (pH 7.4). Encapsulated insulin could be released from the polymersomes only in the presence of sugars under physiologically relevant pH conditions.