2'-acrylamidoethyl-2,3,4,6-tetra-O-acetyl-β-d-glucopyranoside | 1175642-04-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2'-acrylamidoethyl-2,3,4,6-tetra-O-acetyl-β-d-glucopyranoside
• 英文别名: N-acryloyl-2-aminoethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[2-(prop-2-enoylamino)ethoxy]oxan-2-yl]methyl acetate
• CAS: 1175642-04-2
• 化学式: C₁₉H₂₇NO₁₁
• 分子量: 445.423
• InChiKey: QYJQRZYFUURPIC-IQZDNPOKSA-N

物化性质

• 沸点：
  563.9±50.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  31
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  153
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2'-acrylamidoethyl-2,3,4,6-tetra-O-acetyl-β-d-glucopyranoside 在 甲醇 、 sodium methylate 作用下， 生成 N-(β-glycosyloxy)ethyl acrylamide
  参考文献：
  名称：

  含有吡喃糖形式碳水化合物残基的功能性聚合物刷的合成及其与蛋白质的特异性和非特异性相互作用

  摘要：

  含有不同糖残基，2'-acrylamidoethyl-α-三新颖的N-取代的丙烯酰胺单体d -mannopyranoside，2'-acrylamidoethyl-β- d吡喃葡萄糖苷，和2'-acrylamidoethyl-β- d -galactopyranoside，在吡喃糖形式被合成。通过使用未保护的糖单体的表面引发的原子转移自由基聚合（SI-ATRP），在硅基底上制备了相应的糖聚合物刷。糖聚合物刷的形成通过椭圆光度法，ATR-FTIR，水接触角分析，原子力显微镜分析和X射线光电子能谱得到了很好的表征。彻底研究了卤素，配体和溶剂对聚合的影响。结果表明，CuCl / CuCl 2最佳比例的Cu（I）/ Cu（II）的/ tris（2-二甲基氨基乙基）胺（Me 6 TREN）催化体系生产的糖聚合物具有高分子量（M n = 44-140 kDa）和相对窄的分子量分布（PDI = 1.4）。所得糖聚合物刷的干厚度（10-36

  DOI：

  10.1021/bm100882q
• 作为产物：
  描述：

  2-叠氮乙基-2,3,4,6-四-O-乙酰-β-D-吡喃葡萄糖苷 在 palladium 10% on activated carbon 、 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 2'-acrylamidoethyl-2,3,4,6-tetra-O-acetyl-β-d-glucopyranoside
  参考文献：
  名称：

  含有吡喃糖形式碳水化合物残基的功能性聚合物刷的合成及其与蛋白质的特异性和非特异性相互作用

  摘要：

  含有不同糖残基，2'-acrylamidoethyl-α-三新颖的N-取代的丙烯酰胺单体d -mannopyranoside，2'-acrylamidoethyl-β- d吡喃葡萄糖苷，和2'-acrylamidoethyl-β- d -galactopyranoside，在吡喃糖形式被合成。通过使用未保护的糖单体的表面引发的原子转移自由基聚合（SI-ATRP），在硅基底上制备了相应的糖聚合物刷。糖聚合物刷的形成通过椭圆光度法，ATR-FTIR，水接触角分析，原子力显微镜分析和X射线光电子能谱得到了很好的表征。彻底研究了卤素，配体和溶剂对聚合的影响。结果表明，CuCl / CuCl 2最佳比例的Cu（I）/ Cu（II）的/ tris（2-二甲基氨基乙基）胺（Me 6 TREN）催化体系生产的糖聚合物具有高分子量（M n = 44-140 kDa）和相对窄的分子量分布（PDI = 1.4）。所得糖聚合物刷的干厚度（10-36

  DOI：

  10.1021/bm100882q

文献信息

• Synthesis and characterisation of glucose-functional glycopolymers and gold nanoparticles: study of their potential interactions with ovine red blood cells
  作者：Laura E. Wilkins、Daniel J. Phillips、Robert C. Deller、Gemma-Louise Davies、Matthew I. Gibson

  DOI：10.1016/j.carres.2014.09.009

  日期：2015.3

  Carbohydrate-protein interactions can assist with the targeting of polymer- and nano-delivery systems. However, some potential protein targets are not specific to a single cell type, resulting in reductions in their efficacy due to undesirable non-specific cellular interactions. The glucose transporter 1 (GLUT-1) is expressed to different extents on most cells in the vasculature, including human red blood cells and on cancerous tissue. Glycosylated nanomaterials bearing glucose (or related) carbohydrates, therefore, could potentially undergo unwanted interactions with these transporters, which may compromise the nanomaterial function or lead to cell agglutination, for example. Here, RAFT polymerisation is employed to obtain well-defined glucose-functional glycopolymers as well as glycosylated gold nanoparticles. Agglutination and binding assays did not reveal any significant binding to ovine red blood cells, nor any haemolysis. These data suggest that gluco-functional nanomaterials are compatible with blood, and their lack of undesirable interactions highlights their potential for delivery and imaging applications. (C) 2014 Elsevier Ltd. All rights reserved.
• Nanostructured styrenic co-polymers containing glucopyranosyl residues and their functionalization
  作者：Marco Pocci、Silvana Alfei、Francesco Lucchesini、Vincenzo Bertini、Barbara Idini

  DOI：10.1016/j.tet.2009.05.033

  日期：2009.7

  Sugar-based co-polymers with saccharidic units in stable cyclic form and nanometric morphologies stabilized through crosslinking, adaptable through specific functionalizations to biochemical interaction studies with copper-containing amine oxidases, were synthesized from appropriate monomers and macromonomers. The most promising nanospherical co-polymer obtained, containing beta-D-glucopyranosidic units, was employed in functionalization reactions with the help of model molecules, achieving useful transformations mainly at the 6-position and to a minor extent at the 2-position of the saccharidic system. (C) 2009 Elsevier Ltd. All rights reserved.