2-(acetylthio)ethyl tetra-O-acetyl-α-D-mannopyranoside | 212309-05-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(acetylthio)ethyl tetra-O-acetyl-α-D-mannopyranoside
• 英文别名: [(2R,3R,4S,5S,6S)-3,4,5-triacetyloxy-6-(2-acetylsulfanylethoxy)oxan-2-yl]methyl acetate
• CAS: 212309-05-2
• 化学式: C₁₈H₂₆O₁₁S
• 分子量: 450.464
• InChiKey: GXVQXAUNYBLARZ-ZBRFXRBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  30
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  166
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2-(acetylthio)ethyl tetra-O-acetyl-α-D-mannopyranoside 在 sodium methylate 、 potassium carbonate 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.75h， 生成
  参考文献：
  名称：

  Convergent synthesis of fluorescein-labelled lysine-based cluster glycosides

  摘要：

  The synthesis of fluorescein-labelled lysinyl trees, containing 2, 4 or 8 manno- or galactoside residues, is reported. These lysine-based cluster glycosides have been readily assembled by coupling amino-functionalized, N-chloroacetylated-L-lysinyl trees with fluorescein-isothiocyanate (FITC) and performing a thioether chemoselective ligation with fully deprotected glycoside derivatives. The reaction order is governed by the size of the lysinyl trees; the labelling/thioetherification steps can be performed in an one pot procedure, thus allowing an easy access to glycodendrimers designed to study the dendritic cells' mannose receptor. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01535-x
• 作为产物：
  描述：

  2-bromoethyl α-D-mannopyranoside 在 高氯酸 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 反应 3.0h， 生成 2-(acetylthio)ethyl tetra-O-acetyl-α-D-mannopyranoside
  参考文献：
  名称：

  Convergent synthesis of fluorescein-labelled lysine-based cluster glycosides

  摘要：

  The synthesis of fluorescein-labelled lysinyl trees, containing 2, 4 or 8 manno- or galactoside residues, is reported. These lysine-based cluster glycosides have been readily assembled by coupling amino-functionalized, N-chloroacetylated-L-lysinyl trees with fluorescein-isothiocyanate (FITC) and performing a thioether chemoselective ligation with fully deprotected glycoside derivatives. The reaction order is governed by the size of the lysinyl trees; the labelling/thioetherification steps can be performed in an one pot procedure, thus allowing an easy access to glycodendrimers designed to study the dendritic cells' mannose receptor. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01535-x

文献信息

• Gold<i>Manno</i>-Glyconanoparticles: Multivalent Systems to Block HIV-1 gp120 Binding to the Lectin DC-SIGN
  作者：Olga Martínez-Ávila、Karolin Hijazi、Marco Marradi、Caroline Clavel、Colin Campion、Charles Kelly、Soledad Penadés

  DOI：10.1002/chem.200900923

  日期：2009.9.28

  ending in thiol groups, which enable attachment of the glycoconjugates to the gold surface, have been prepared. manno‐GNPs with different spacers and variable density of mannose (oligo)saccharides have been obtained and characterized. Surface plasmon resonance (SPR) experiments with selected manno‐GNPs have been performed to study their inhibition potency towards DC‐SIGN binding to gp120. The tested manno‐GNPs

  HIV包膜糖蛋白gp120利用其表面的高甘露糖簇将树突状细胞靶向C型凝集素树突状细胞特异的细胞内粘附分子-3夺取非整联蛋白（DC‐SIGN）。模仿寡聚甘露糖苷在病毒表面的簇状存在是设计基于碳水化合物的抗病毒剂的一种策略。受gp120簇呈递的生物启发，我们设计并准备了一个小型多价水溶性金糖纳米颗粒（manno- GNP）库，其展示了高甘露糖十一碳糖Man 9 GlcNAc 2的截短的（寡聚）甘露糖苷。并测试了它们作为DC-SIGN与gp120结合的抑制剂。这些糖纳米颗粒是DC-SIGN的配体，DC-SIGN还可在感染的早期阶段通过对相关聚糖的特异性识别而与大量病原体相互作用。制备了具有以硫醇基结尾的不同间隔基的（寡）甘露糖苷，其使得糖缀合物能够附着至金表面。低聚甘露已经获得和表征具有不同间隔和甘露糖（低聚）糖的可变密度的GNP。已经进行了使用选定的甘露糖-GNP的表面等离振子共振（SPR）实
• 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。
• Thioctic acid amides: convenient tethers for achieving low nonspecific protein binding to carbohydrates presented on gold surfaces
  作者：Rositsa Karamanska、Balaram Mukhopadhyay、David A. Russell、Robert A. Field

  DOI：10.1039/b503843j

  日期：——

  The thioctic acid amides of 2′-aminoethyl α-D-mannopyranoside and 2′-aminoethyl α-1,3-D-mannopyranosyl (α-1,6-D-mannopyranosyl)-α-D-mannopyranoside presented on both planar and nanoparticle gold surfaces give higher specific and lower non-specific protein binding than the related 2′-thioethyl glycosides.

  2'-氨基乙基 α-D-吡喃甘露糖苷和 2'-氨基乙基 α-1,3-D-吡喃甘露糖基 (α-1,6-D-吡喃甘露糖基)-α-D-吡喃甘露糖苷的硫辛酸酰胺在平面和平面上均呈现纳米颗粒金表面比相关的 2'-硫乙基糖苷具有更高的特异性和更低的非特异性蛋白质结合。
• A facile one-pot sonochemical synthesis of surface-coated mannosyl protein microspheres for detection and killing of bacteria
  作者：Natalia Skirtenko、Michal Richman、Yeshayahu Nitzan、Aharon Gedanken、Shai Rahimipour

  DOI：10.1039/c1cc13518j

  日期：——

  We report a remarkably facile one-pot sonochemical approach to prepare protein microspheres whose shells are covalently decorated with a mannosyl derivative to target Escherichia coli (E. coli), while their cores are encapsulated with tetracycline. Conjugated microspheres induced the agglutination of E. coli and increased the anti-bacterial activity of the encapsulated tetracycline by five fold.

  我们报告了一种非常简便的一锅式超声化学方法，用于制备蛋白质微球，其外壳通过共价键与甘露糖衍生物结合，以靶向大肠杆菌（E. coli），而其内核则被四环素包裹。共轭微球诱导大肠杆菌凝集，并将包裹的四环素的抗菌活性提高了五倍。