2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranose 1-dibenzylphosphate | 147072-58-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranose 1-dibenzylphosphate
• CAS: 147072-58-0
• 化学式: C₂₈H₃₄NO₁₂P
• 分子量: 607.551
• InChiKey: LRZDQJGYXBTJCA-RKFAPSRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  42.0
• 可旋转键数：
  13.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  161.99
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranose 1-dibenzylphosphate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 苯 为溶剂， 反应 1.0h， 生成 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl phosphate
  参考文献：
  名称：

  Yamazaki, Tatsumi; Warren, Christopher D.; Herscovics, Annette, Canadian Journal of Chemistry, 1981, vol. 59, p. 2247 - 2252

  摘要：

  DOI：
• 作为产物：
  描述：

  D-半乳糖胺五乙酸酯 在 1H-1,2,4-三唑 、 双氧水 、 苄胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranose 1-dibenzylphosphate
  参考文献：
  名称：

  Sim, Mui Mui; Kondo, Hirosato; Wong, Chi-Huey, Journal of the American Chemical Society, 1993, vol. 115, # 6, p. 2260 - 2267

  摘要：

  DOI：

文献信息

• Design, synthesis and biological evaluation of carbohydrate-functionalized cyclodextrins and liposomes for hepatocyte-specific targeting
  作者：Gonçalo J. L. Bernardes、Raghavendra Kikkeri、Maha Maglinao、Paola Laurino、Mayeul Collot、Sung You Hong、Bernd Lepenies、Peter H. Seeberger

  DOI：10.1039/c0ob00372g

  日期：——

  Targeting glycan-binding receptors is an attractive strategy for cell-specific drug and gene delivery. The C-type lectin asialoglycoprotein receptor (ASGPR) is particularly suitable for liver-specific delivery due to its exclusive expression by parenchymal hepatocytes. In this study, we designed and developed an efficient synthesis of carbohydrate-functionalized β-cyclodextrins (βCDs) and liposomes for hepatocyte-specific delivery. For targeting of ASGPR, rhodamine B-loaded βCDs were functionalized with glycodendrimers. Liposomes were equipped with synthetic glycolipids containing a terminal D-GalNAc residue to mediate binding to ASGPR. Uptake studies in the human hepatocellular carcinoma cell line HepG2 demonstrated that βCDs and liposomes displaying terminal D-Gal/D-GalNAc residues were preferentially endocytosed. In contrast, uptake of βCDs and liposomes with terminal D-Man or D-GlcNAc residues was markedly reduced. The D-Gal/D-GalNAc-functionalized βCDs and liposomes presented here enable hepatocyte-specific targeting. Gal-functionalized βCDs are efficient molecular carriers to deliver doxorubicin in vitro into hepatocytes and induce apoptosis.

  针对糖结合受体的策略在细胞特异性药物和基因传递中具有吸引力。C型凝集素脱唾液酸糖蛋白受体（ASGPR）由于其仅由实质性肝细胞表达，特别适合于肝脏特异性传递。在本研究中，我们设计并开发了一种高效的碳水化合物功能化β-环糊精（βCDs）和脂质体的合成方法，用于肝细胞特异性传递。为了针对ASGPR进行靶向，罗丹明B负载的βCDs通过糖树枝状聚合物进行功能化。脂质体配备含有末端D-GalNAc残基的合成糖脂，以介导与ASGPR的结合。在人肝细胞癌细胞系HepG2中的摄取研究表明，显示末端D-Gal/D-GalNAc残基的βCDs和脂质体优先被内吞。相比之下，具有末端D-Man或D-GlcNAc残基的βCDs和脂质体的摄取明显减少。这里展示的D-Gal/D-GalNAc功能化的βCDs和脂质体实现了肝细胞特异性靶向。Gal功能化的βCDs是有效的分子载体，能够在体外将多柔比星传递到肝细胞并诱导凋亡。
• Reliable Synthesis of Various Nucleoside Diphosphate Glycopyranoses
  作者：Saskia Wolf、Tanja Zismann、Nathalie Lunau、Chris Meier

  DOI：10.1002/chem.200900572

  日期：2009.8.3

  A reliable and high yielding synthetic pathway for the synthesis of the biologically highly important class of nucleoside diphosphate sugars (NDP‐sugars) was developed by using various cycloSal‐nucleotides 1 and 9 as active ester building blocks. The reaction with anomerically pure pyranosyl‐1‐phosphates 2 led to the target NDP‐sugars 20–45 in a nucleophilic displacement reaction, which cleaves the

  通过使用各种环Sal-核苷酸1和9作为活性酯结构单元，开发了一种可靠且高产的合成途径，用于合成生物学上非常重要的一类核苷二磷酸糖（NDP-糖）。与端基异构体纯的吡喃糖基-1-磷酸的反应2导致目标NDP-糖20 - 45在亲核取代反应，其切割的环在端基异构体纯的形式萨尔部分。作为核苷，可使用胞苷，尿苷，胸苷，腺苷，2'-脱氧鸟苷和2'，3'-二脱氧-2'，3'-二脱氢胸苷，而D-葡萄糖，D的磷酸盐引入了半乳糖，D-甘露糖，D - N-氨基葡萄糖，D - N-半乳糖胺，D-岩藻糖，L-岩藻糖以及6-脱氧-D-果糖。