p-(N-acrylamido)phenyl 2-acetamido-2-deoxy-6-sulfo-β-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-(N-acrylamido)phenyl 2-acetamido-2-deoxy-6-sulfo-β-D-glucopyranoside
• 英文别名: p-(N-acrylamido)phenyl-β-D-glucuronic acid；(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[4-(prop-2-enoylamino)phenoxy]oxane-2-carboxylic acid
• 化学式: C₁₅H₁₇NO₈
• 分子量: 339.302
• InChiKey: LRWFBYSEJVDOTJ-DKBOKBLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  146
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  4-硝基苯-Β-D-葡萄糖苷酸 在 盐酸 、 palladium on activated charcoal 、 氢气 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 52.0h， 生成 p-(N-acrylamido)phenyl 2-acetamido-2-deoxy-6-sulfo-β-D-glucopyranoside
  参考文献：
  名称：

  Syntheses of sulfated glycopolymers and analyses of their BACE-1 inhibitory activity

  摘要：

  The glycopolymers for glycosaminoglycan mimic were synthesized, and the inhibitory effects of Alzheimer's beta-secretase (BACE-1) were examined. The regio-selective sulfation was conducted on N-acetyl glucosamine (GlcNAc), and the acrylamide derivatives were synthesized with the consequent sulfated GlcNAc. The glycopolymers were synthesized with acrylamide using radical initiator. The glycopolymer with sulfated GlcNAc showed the strong inhibitory effect on BACE-1, and the inhibitory effects were dependent on the sulfation positions. Especially, glycopolymers carrying 3,4,6-O-sulfo-GlcNAc showed the strong inhibitory effect. The docking simulation suggested that glycopolymers bind to the active site of BACE-1. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.09.057

文献信息

• Interaction Analyses of Amyloid β Peptide (1–40) with Glycosaminoglycan Model Polymers
  作者：Yoshiko Miura、Hikaru Mizuno

  DOI：10.1246/bcsj.20100094

  日期：2010.9.15

  We synthesized a novel glycopolymer library with 6-sulfo-GlcNAc and glucuronic acid (GlcA) based on the structure of glycosaminoglycans. The molecular weights of the polymers were controlled via living radical polymerization. The interactions of Aβ(1–40) with glycopolymers were analyzed by inhibition activity of protein aggregation using ThT fluorescence assay, atomic force microscopy observation, and CD spectra. The inhibition activity of Aβ was much affected by the sugar structure and molecular weight of the polymer. The glycopolymers carrying 6-sulfo-GlcNAc showed inhibition activity toward Aβ aggregate, and those with 6-suflo-GlcNAc and GlcA showed the strong inhibition activity. The glycopolymer libraries yielded valuable information about Aβ aggregate with glycosaminoglycans.

  我们根据糖胺聚糖的结构，合成了一个含有 6-sulfo-GlcNAc 和葡萄糖醛酸 (GlcA) 的新型糖聚合物库。聚合物的分子量是通过活自由基聚合控制的。利用 ThT 荧光测定法、原子力显微镜观察和 CD 光谱分析了 Aβ(1-40)与糖聚合物的相互作用对蛋白质聚集的抑制活性。糖聚合物的糖结构和分子量对 Aβ 的抑制活性有很大影响。含有6-sulfo-GlcNAc的糖聚合物对Aβ聚集体具有抑制活性，而含有6-suflo-GlcNAc和GlcA的糖聚合物则具有很强的抑制活性。糖聚合物库提供了有关 Aβ 与糖胺聚糖聚合的宝贵信息。
• [EN] ABIOTIC ANTI-VEGF NANOPARTICLE<br/>[FR] NANOPARTICULE ANTI-VEGF ABIOTIQUE
  申请人：UNIV CALIFORNIA

  公开号：WO2018039509A1

  公开（公告）日：2018-03-01

  The present invention relates generally to compositions and methods comprising abiotic, synthetic polymers with affinity and specificity to proteins. The synthetic polymers are an improvement over biological agents by providing a simpler, less expensive, and customizable platform for binding to proteins. In one embodiment, the compositions and methods relate to synthetic polymers with affinity and specificity to vascular endothelial growth factor (VEGF). In one embodiment, the compositions are useful for treating diseases and disorders related to the overexpression of VEGF. In one embodiment, the compositions are useful for treating cancer. In one embodiment, the compositions are useful for detecting VEGF levels from biological samples. In one embodiment, the compositions are useful for detecting overexpression of VEGF from biological samples. In one embodiment, the compositions are used to diagnose cancer.

  本发明一般涉及包含对蛋白质具有亲和力和特异性的无生物合成聚合物的组合物和方法。这些合成聚合物通过提供一个更简单、更便宜和可定制的平台，改进了生物试剂，用于结合蛋白质。在一个实施例中，这些组合物和方法涉及具有对血管内皮生长因子（VEGF）具有亲和力和特异性的合成聚合物。在一个实施例中，这些组合物适用于治疗与VEGF过度表达相关的疾病和紊乱。在一个实施例中，这些组合物适用于治疗癌症。在一个实施例中，这些组合物适用于从生物样本中检测VEGF水平。在一个实施例中，这些组合物适用于从生物样本中检测VEGF过度表达。在一个实施例中，这些组合物用于诊断癌症。
• Syntheses of sulfated glycopolymers and analyses of their BACE-1 inhibitory activity
  作者：Yuri Nishimura、Hiroki Shudo、Hirokazu Seto、Yu Hoshino、Yoshiko Miura

  DOI：10.1016/j.bmcl.2013.09.057

  日期：2013.12

  The glycopolymers for glycosaminoglycan mimic were synthesized, and the inhibitory effects of Alzheimer's beta-secretase (BACE-1) were examined. The regio-selective sulfation was conducted on N-acetyl glucosamine (GlcNAc), and the acrylamide derivatives were synthesized with the consequent sulfated GlcNAc. The glycopolymers were synthesized with acrylamide using radical initiator. The glycopolymer with sulfated GlcNAc showed the strong inhibitory effect on BACE-1, and the inhibitory effects were dependent on the sulfation positions. Especially, glycopolymers carrying 3,4,6-O-sulfo-GlcNAc showed the strong inhibitory effect. The docking simulation suggested that glycopolymers bind to the active site of BACE-1. (C) 2013 Elsevier Ltd. All rights reserved.