[(2R,3S,4R,5R,6R)-3,4-diacetyloxy-6-azido-5-[(2-methylpropan-2-yl)oxycarbonylamino]oxan-2-yl]methyl acetate | 1196977-77-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3S,4R,5R,6R)-3,4-diacetyloxy-6-azido-5-[(2-methylpropan-2-yl)oxycarbonylamino]oxan-2-yl]methyl acetate
• CAS: 1196977-77-1
• 化学式: C₁₇H₂₆N₄O₉
• 分子量: 430.415
• InChiKey: MDQWHPZTYPHCOH-KJWHEZOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  141
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  [(2R,3S,4R,5R,6R)-3,4-diacetyloxy-6-azido-5-[(2-methylpropan-2-yl)oxycarbonylamino]oxan-2-yl]methyl acetate 、 在 copper(II) sulfate 、 sodium ascorbate 作用下， 以 四氢呋喃 、 水 为溶剂， 以86%的产率得到
  参考文献：
  名称：

  Water-soluble conjugated polyelectrolyte with pendant glycocluster: Synthesis and its interaction with heparin

  摘要：

  A novel fluorescent conjugated polyelectrolyte with pendant glucosamine hydrochloride clusters was prepared through Cu(I)-catalyzed azide/alkyne "click" ligation and Suzuki coupling polymerization. Compared with monosugar-functionalized conjugated polymer, the water-solubility and fluorescence quantum yield of the glycocluster-containing polymer (P-3) were significantly improved. As a glucosamine-containing cationic fluorescent polyelectrolyte, the water-soluble fluorescent polymer can interact with heparin through electrostatic bindings, which induce great fluorescence quenching of P-3 due to the polymer aggregation. Furthermore, upon treatment of the P-3 heparin ensemble with protamine, the fluorescence emission of P-3 recovered since the protamine possesses a competitively strong binding affinity to the heparin and thus results in the release of the fluorescent glycopolymer P-3 from the P-3 heparin ensemble. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.polymer.2010.11.048

文献信息

• Cationic cyclotriveratrylene-based glycoconjugate and its interaction with fullerene
  作者：Li-Juan Feng、Hui Li、Qi Chen、Bao-Hang Han

  DOI：10.1039/c3ra40432c

  日期：——

  Fullerenes exhibit interesting biological activities both in vitro and in vivo. However, the low solubility of fullerenes in aqueous media appears to be a major problem for their biological application. To exploit water-soluble macrocyclic host systems to improve the water-solubility of fullerene, a cationic water-soluble CTV derivative containing glucosamine hydrochloride (CTV-GH) is synthesized and well characterized. The supramolecular complexation between CTV-GH and C60 was investigated in organic solvent and aqueous solution, respectively, and confirmed by fluorescence, UV-vis, and Raman spectra. The CTV derivative exhibits a distinct photoluminescence, which can be used to conveniently detect its interaction with C60 through spectrofluorometric titration. CTV-GH can bind C60 in toluene–DMSO solution with the association constant Ka = 4.36 × 105 M−1 calculated on the hypothesis of forming a supramolecular complex with 1 : 1 molar ratio at 298 K. In an aqueous solution, C60 has no absorption intensity due to its insolubility. However, in the presence of CTV-GH, a new characteristic peak of C60 at 342 nm in the UV-vis absorption spectrum was observed for the C60–CTV-GH complex and its intensity greatly increases over 24 h, which proves that CTV-GH can bind C60 in aqueous solution to form a water-soluble complex. The host–guest interaction between sugar-bearing CTV and C60 in aqueous solution will boost the potential biological applications of C60.

  富勒烯在体外和体内都表现出有趣的生物活性。然而，富勒烯在水介质中的低溶解度似乎是其生物应用的一个主要问题。为了利用水溶性大环宿主系统来提高富勒烯的水溶性，我们合成了一种含有氨基葡萄糖盐酸盐的阳离子水溶性 CTV 衍生物（CTV-GH），并对其进行了表征。研究人员分别在有机溶剂和水溶液中考察了 CTV-GH 与 C60 的超分子络合，并通过荧光、紫外-可见光和拉曼光谱进行了证实。CTV 衍生物表现出明显的光致发光，可通过光谱荧光滴定法方便地检测其与 C60 的相互作用。CTV-GH 能在甲苯-DMSO 溶液中与 C60 结合，其结合常数 Ka = 4.36 × 105 M-1 是根据在 298 K 下形成摩尔比为 1 ：在水溶液中，C60 由于不溶解而没有吸收强度。然而，在 CTV-GH 的存在下，C60-CTV-GH 复合物的紫外-可见吸收光谱在 342 纳米处出现了一个新的 C60 特征峰，且其强度在 24 小时内大幅增加，这证明 CTV-GH 可以在水溶液中与 C60 结合形成水溶性复合物。含糖 CTV 与 C60 在水溶液中的主客体相互作用将促进 C60 的潜在生物应用。
• Glucosamine hydrochloride functionalized tetraphenylethylene: A novel fluorescent probe for alkaline phosphatase based on the aggregation-induced emission
  作者：Qi Chen、Ning Bian、Chun Cao、Xi-Long Qiu、Ai-Di Qi、Bao-Hang Han

  DOI：10.1039/c002894k

  日期：——

  Grafting of glucosamine hydrochloride moieties to tetraphenylethylene (TPE) motif furnished a novel cationic water-soluble tetraphenylethylene derivative (GH-TPE). With aggregation-induced emission properties, GH-TPE was used for fluorometric detection to alkaline phosphatase through enzyme-triggered de-aggregation of the ensemble of GH-TPE and substrate.

  将氨基葡萄糖盐酸盐接枝到四苯基乙烯（TPE）基团上，产生了一种新型阳离子水溶性四苯基乙烯衍生物（GH-TPE）。GH-TPE 具有聚集诱导发射特性，通过酶触发 GH-TPE 和底物集合的去聚集，可用于碱性磷酸酶的荧光检测。
• Sugar-functionalized triptycenes used for dispersion of single-walled carbon nanotubes in aqueous solution by supramolecular interaction
  作者：Hui Li、Qi Chen、Bao-Hang Han

  DOI：10.1039/c5nj03075g

  日期：——

  Noncovalent functionalization of carbon nanotubes (CNTs) can not only preserve their unique properties, but also improve their solubility in aqueous solutions. Herein, two water-soluble sugar-functionalized triptycene derivatives were synthesized and interacted with single-walled carbon nanotubes (SWCNTs) to form stable homogeneous aqueous solutions, which indicated the development of a successful

  碳纳米管（CNT）的非共价官能化不仅可以保留其独特的性能，还可以提高其在水溶液中的溶解度。本文中，合成了两种水溶性的糖官能化的三茂萜衍生物，并与单壁碳纳米管（SWCNT）相互作用形成稳定的均相水溶液，这表明开发了一种成功的方法将SWCNT分散在水中。通过吸收，荧光和拉曼光谱，可以充分表征三茂金属衍生物和SWCNT之间形成的超分子系统。此外，基于形状拟合的三萜系还显示出对具有特定直径的SWCNT的选择性。