2-(2-(2-thioacetylethoxy)ethoxy)ethoxy-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside | 1122489-25-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2-(2-thioacetylethoxy)ethoxy)ethoxy-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside
• 英文别名: 2-(2-(2-acetylthioethoxy)ethoxy)ethyl-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside；2-[2-(2-(acetylthio)ethoxy)ethoxy]ethyl α-D-mannopyranoside-2,3,4,6-tetraacetate；2-[2-(2-acetylthio)ethoxy]ethyl 2,3,4,6-tetraacetate-α-D-mannopyranoside；2-[2-(2-acetylthio)ethoxy]ethyl-2,3,4,6-tetraacetate-α-D-mannopyranoside
• CAS: 1122489-25-1
• 化学式: C₂₂H₃₄O₁₃S
• 分子量: 538.57
• InChiKey: DILOQKIWNBMBCS-AANPDWTMSA-N

物化性质

• 沸点：
  579.2±50.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  36.0
• 可旋转键数：
  15.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  159.19
• 氢给体数：
  0.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  2-(2-(2-thioacetylethoxy)ethoxy)ethoxy-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以93%的产率得到2-[2-(2-chloroethoxy)ethoxy]ethyl α-D-mannopyranoside
  参考文献：
  名称：

  卟啉与外周硫醇结合的金（I）配合物，以增强光动力治疗。

  摘要：

  合成与N-杂环卡宾金（I）配合物融合的卟啉，并用作光敏剂，对MCF-7癌细胞进行光动力治疗。数据表明，观察到的光动力效应取决于与金（I）连接的辅助巯基配体的性质。

  DOI：

  10.1002/chem.201702975
• 作为产物：
  描述：

  2-[2-(2-ethoxyethoxy)ethoxy]ethyl, 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 在 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 2-(2-(2-thioacetylethoxy)ethoxy)ethoxy-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside
  参考文献：
  名称：

  卟啉与外周硫醇结合的金（I）配合物，以增强光动力治疗。

  摘要：

  合成与N-杂环卡宾金（I）配合物融合的卟啉，并用作光敏剂，对MCF-7癌细胞进行光动力治疗。数据表明，观察到的光动力效应取决于与金（I）连接的辅助巯基配体的性质。

  DOI：

  10.1002/chem.201702975

文献信息

• Multivalent recognition of lectins by glyconanoparticle systems
  作者：Eugene Mahon、Teodor Aastrup、Mihail Barboiu

  DOI：10.1039/c002652b

  日期：——

  Multivalent recognition of lectin layers by glyconanoparticle sugar-clusters has been used to study the carbohydrate–protein interactions in a QCM sensing setup.

  多价凝集素层通过糖纳米颗粒糖簇的识别已被用于在QCM传感系统中研究碳水化合物-蛋白质相互作用。
• Glucose- and pH-Responsive Controlled Release of Cargo from Protein-Gated Carbohydrate-Functionalized Mesoporous Silica Nanocontainers
  作者：Shanshan Wu、Xuan Huang、Xuezhong Du

  DOI：10.1002/anie.201300958

  日期：2013.5.17

  Learning to let go: Controlled release of cargo (purple cubes) from lectin (blue squares)‐gated nanopores was achieved using mannose (green loops)‐functionalized mesoporous silica (see scheme). The protein nanogates could be opened either by decreasing the pH of the buffer or by adding competing glucose (yellow rings) to release the cargo from the pores.

  学会放手：使用甘露糖（绿色环）功能化的介孔二氧化硅（见方案）实现了从凝集素（蓝色方块）门控的纳米孔中受控释放货物（紫色立方体）。可以通过降低缓冲液的pH值或添加竞争性葡萄糖（黄色环）从孔中释放出货物来打开蛋白质纳米门。
• Bacterial detection using carbohydrate-functionalised CdS quantum dots: a model study exploiting E. coli recognition of mannosides
  作者：Balaram Mukhopadhyay、Maristela B. Martins、Rositsa Karamanska、David A. Russell、Robert A. Field

  DOI：10.1016/j.tetlet.2008.12.029

  日期：2009.2

  Mannose-coated CdS quantum dots (Man-QDs) were prepared in a facile aqueous, one-pot process that exploits the self-assembly of thiolated mannose in the presence of CdS under reducing conditions. The resulting similar to 15 nm diameter nanoparticles produce an intense, broad luminescence emission centred at 550 nm. These Man-QDs induce luminescent aggregates of Escherichia coli which can be used to detect bacteria in cell suspensions containing as few as 10(4) E. coli per mL. The aggregation process is dependent on the E coli cell surface FimH mannose-specific lectin. The recognition and subsequent detection of the E. coli using the Man-QD has been shown to be specific as aggregation does not occur either with an E. coli strain defective in the FimH lectin or with galactose-coated QDs. (C) 2008 Elsevier Ltd. All rights reserved.
• Kikkeri, Raghavendra; Lepenies, Bernd; Adibekian, Alexander, Journal of the American Chemical Society, 2009, vol. 131, p. 2110 - 2112
  作者：Kikkeri, Raghavendra、Lepenies, Bernd、Adibekian, Alexander、Laurino, Paola、Seeberger, Peter H.

  DOI：——

  日期：——
• Design of a “Turn-Off/Turn-On” Biosensor: Understanding Carbohydrate-Lectin Interactions for Use in Noncovalent Drug Delivery
  作者：Bala Kishan Gorityala、Zhiqiang Lu、Min Li Leow、Jimei Ma、Xue-Wei Liu

  DOI：10.1021/ja306288p

  日期：2012.9.19

  A low-cost and highly sensitive biosensor system is designed to investigate carbohydrate-lectin interactions. This combination of glyco-gold nanoparticles and boronic acid biosensor system opens a way to study noncovalent drug delivery.