β-D-maltoheptaosyl azide | 932370-50-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-D-maltoheptaosyl azide
• CAS: 932370-50-8
• 化学式: C₄₂H₇₁N₃O₃₅
• 分子量: 1178.02
• InChiKey: BAYHXRZNHJUNFB-CAYDELFDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -14.96
• 重原子数：
  80.0
• 可旋转键数：
  20.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  613.81
• 氢给体数：
  22.0
• 氢受体数：
  36.0

反应信息

• 作为反应物：
  描述：

  β-D-maltoheptaosyl azide 在 [(2,9-dimethyl-1,10-phenanthroline)-Pd(μ-OAc)]₂(OTf)₂ 、 对苯醌 作用下， 以 二甲基亚砜 为溶剂， 以47%的产率得到β-D-3-ketomaltoheptaosyl azide
  参考文献：
  名称：

  未保护的1,4个连接葡聚糖的区域选择性氧化†

  摘要：

  钯催化的醇氧化可以对未保护的1,4连接的葡聚糖进行化学和区域选择性修饰。1,7连接的葡聚糖直至7-mer的两步双功能化证明了这一点。引入端基叠氮化物后，对末端C3-OH官能团进行高度区域选择性的单氧化。如4-草酸巴豆酸酯互变异构酶的半胱氨酸突变体与生物素的缀合所证明的，所得的正交双官能化寡糖是PEG-间隔子的可行替代物。

  DOI：

  10.1039/c6ob00608f
• 作为产物：
  描述：

  maltoheptaose 在 sodium azide 、 CIP 、 N,N-二异丙基乙胺 作用下， 以 水 为溶剂， 以49%的产率得到β-D-maltoheptaosyl azide
  参考文献：
  名称：

  未保护的1,4个连接葡聚糖的区域选择性氧化†

  摘要：

  钯催化的醇氧化可以对未保护的1,4连接的葡聚糖进行化学和区域选择性修饰。1,7连接的葡聚糖直至7-mer的两步双功能化证明了这一点。引入端基叠氮化物后，对末端C3-OH官能团进行高度区域选择性的单氧化。如4-草酸巴豆酸酯互变异构酶的半胱氨酸突变体与生物素的缀合所证明的，所得的正交双官能化寡糖是PEG-间隔子的可行替代物。

  DOI：

  10.1039/c6ob00608f

文献信息

• One-step conversion of unprotected sugars to β-glycosyl azides using 2-chloroimidazolinium salt in aqueous solution
  作者：Tomonari Tanaka、Hikaru Nagai、Masato Noguchi、Atsushi Kobayashi、Shin-ichiro Shoda

  DOI：10.1039/b905761g

  日期：——

  Various β-glycosyl azides have been synthesized directly in water by the reaction of unprotected sugars and sodium azide mediated by 2-chloro-1,3-dimethylimidazolinium chloride (DMC).

  在 2-氯-1,3-二甲基氯化咪唑啉（DMC）的介导下，通过非保护糖和叠氮化钠的反应，在水中直接合成了各种δ-糖基叠氮化物。
• Stereoselective Protection-Free Modification of 3-Keto-saccharides
  作者：Nittert Marinus、Nabil Tahiri、Margherita Duca、L. M. C. Marc Mouthaan、Simona Bianca、Marco van den Noort、Bert Poolman、Martin D. Witte、Adriaan J. Minnaard

  DOI：10.1021/acs.orglett.0c01986

  日期：2020.7.17

  Unprotected 3-keto-saccharides have become readily accessible via site-selective oxidation, but their protection-free functionalization is relatively unexplored. Here we show that protecting groups are obsolete in a variety of stereoselective modifications of our model substrate methyl alpha-glucopyranoside. This allows the preparation of rare sugars and the installation of click handles and reactive groups. To showcase the applicability of the methodology, maltoheptaose has been converted into a chemical probe, and the rare sugar evalose has been synthesized.
• Sweet Block Copolymer Nanoparticles: Preparation and Self-Assembly of Fully Oligosaccharide-Based Amphiphile
  作者：Samuel de Medeiros Modolon、Issei Otsuka、Sébastien Fort、Edson Minatti、Redouane Borsali、Sami Halila

  DOI：10.1021/bm3000138

  日期：2012.4.9

  The preparation of biocompatible nanocarriers that have potential applications in the cosmetic and health industries is highly desired. The self-assembly of amphiphilic block copolymers displaying biosourced polysaccharides at the surface is one of the most promising approaches. In the continuity of our works related to the preparation of "hybrid" amphiphilic oligosaccharide-based block copolymers, we present here the design of a new generation of self-assembled nanoparticles composed entirely of oligosaccharide-based amphiphilic block co-oligomers (BCO). These systems are defined by a covalent linkage of the two saccharidic blocks through their reducing end units, resulting in a sweet "head-to-head" connection. As an example, we have prepared and studied a BCO in which the hydrophilic part is composed of a free maltoheptaosyl derivative clicked to a hydrophobic part composed of a peracetylated maltoheptaosyl derivative. This amphiphilic BCO self-assembles to form spherical micelles in water with an average diameter of 30 nm. The efficient enzymatic hydrolysis of the maltoheptaose that constitutes the shell of the micelles was followed by light scattering and colorimetric methods.