N-nitrophenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranoside | 50271-51-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-nitrophenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranoside
• 英文别名: (2R,3R,4R,5R,6S)-5-acetamido-2-(acetoxymethyl)-6-(4-nitrophenoxy)tetrahydro-2H-pyran-3,4-diyl diacetate；p-Nitrophenyltetracetylgalactosaminid；p-Nitrophenyl-2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranosid；(4-Nitro-phenyl)-tetraacetyl-β-galactosaminid；(4-Nitro-phenyl)-(tri-O-acetyl-2-acetylamino-2-desoxy-β-D-galactopyranosid)；(4-nitro-phenyl)-(tri-O-acetyl-2-acetylamino-2-deoxy-β-D-galactopyranoside)；p-nitrophenyl 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-galactopyranoside；[(2R,3R,4R,5R,6S)-5-acetamido-3,4-diacetyloxy-6-(4-nitrophenoxy)oxan-2-yl]methyl acetate
• CAS: 50271-51-7
• 化学式: C₂₀H₂₄N₂O₁₁
• 分子量: 468.417
• InChiKey: IMQGAARHTLJIRK-OUUBHVDSSA-N

物化性质

• 熔点：
  184 °C
• 沸点：
  654.4±55.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  172
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  N-nitrophenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranoside 在 甲醇 、 sodium methylate 作用下， 反应 0.5h， 以100%的产率得到4-硝基苯基-N-乙酰-beta-D-半乳胺
  参考文献：
  名称：

  4-硝基苯基2-乙酰氨基-2-脱氧-β-D-葡萄糖和吡喃半乳糖苷的3-和4-硫代类似物的合成。

  摘要：

  描述了在生命系统中发现的两个主要的2-乙酰氨基-2-脱氧己糖的3-硫和4-硫类似物的4-硝基苯基β-糖苷的合成，GlcNAc和GalNAc。虽然可以通过亲核取代磺酸衍生物与硫代乙酸酯来合成4-硫代类似物，但相邻基团乙酰胺基参与的问题使得必须将氨基磺酸酯中间体用于3-硫代类似物。这些3-和4-硫代类似物用于糖-氨基聚糖，糖蛋白和糖脂中存在的结构的硫代-寡糖类似物的化学-酶促合成中。

  DOI：

  10.1016/j.carres.2007.05.023
• 作为产物：
  描述：

  D-半乳糖胺五乙酸酯 在 四氯化钛 、 potassium hydroxide 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 96.0h， 生成 N-nitrophenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranoside
  参考文献：
  名称：

  Reagents and methods for screening MPS I, II, IIIA, IIIB, IVA, VI, and VII

  摘要：

  Reagents, methods, and kits for assaying enzymes associated with lysosomal storage diseases MPS-I, MPS-II, MPS-IIIA, MPS-IIIB, MPS-IVA, MPS-VI, and MPS VII.

  公开号：

  US11618764B2

文献信息

• Heyworth et al., Journal of the Chemical Society, 1959, p. 4121
  作者：Heyworth et al.

  DOI：——

  日期：——
• Watkins, Biochemical Journal, 1959, vol. 71, p. 261,262
  作者：Watkins

  DOI：——

  日期：——
• Importance of Sialic Acid Residues Illuminated by Live Animal Imaging Using Phosphorylcholine Self-Assembled Monolayer-Coated Quantum Dots
  作者：Tatsuya Ohyanagi、Noriko Nagahori、Ken Shimawaki、Hiroshi Hinou、Tadashi Yamashita、Akira Sasaki、Takashi Jin、Toshihiko Iwanaga、Masataka Kinjo、Shin-Ichiro Nishimura

  DOI：10.1021/ja111201c

  日期：2011.8.17

  Glycans are expected to be one of the potential signal molecules for controlling drug targeting/delivery or long-term circulation of biopharmaceuticals. However, the effect of the carbohydrates of artificially glycosylated derivatives on in vivo dynamic distribution profiles after intravenous injection of model animals remains unclear due to the lack of standardized methodology and a suitable platform. We report herein an efficient and versatile method for the preparation of multifunctional quantum dots (QDs) displaying common synthetic glycosides with excellent solubility and long-term stability in aqueous solution without loss of quantum yields. Combined use of an aminooxy-terminated thiol derivative, 11,11'-dithio bis[undec-11-yl 12-(aminooxyacetyl)amino hexa(ethyleneglycol)], and a phosphorylcholine derivative, 11-mercaptoundecylphosphorylcholine, provided QDs with novel functions for the chemical ligation of ketone-functionalized compounds and the prevention of nonspecific protein adsorption concurrently. In vivo near-infrared (NIR) fluorescence imaging of phosphorylcholine self-assembled monolayer (SAM)-coated QDs displaying various simple sugars (glyco-PC-QDs) after administration into the tail vein of the mouse revealed that distinct long-term delocalization over 2 h can be achieved in cases of QDs modified with alpha-sialic acid residue (Neu5Ac-PC-QDs) and control PC-QDs, while QDs bearing other common sugars, such as alpha-glucose (Glc-PC-QDs), alpha-mannose (Man-PC-QDs), alpha-fucose (Fuc-PC-QDs), lactose (Lac-PC-QDs), beta-glucuronic acid (GlcA-PC-QDs), N-acetyl-beta-D-glucosamine (GlcNAc-PC-QDs), and N-acetyl-beta-D-galactosamine (GalNAc-PC-QDs) residues, accumulated rapidly (5-10 min) in the liver. Sequential enzymatic modifications of GlcNAc-PC-QDs gave Gal beta 1,4GlcNAc-PC-QDs (LacNAc-PC-QDs), Gal beta 1,4(Fuc alpha 1,3)GlcNAc-PC-QDs (Le(x)-PC-QDs), Neu5Ac alpha 2,3Gal beta 1,4GlcNAc-PC-QDs (sialyl LacNAc-PC-QDs), and Neu5Ac alpha 2,3Gal beta 1,4(Fuc alpha 1,3)GlcNAc-PC-QDs (sialyl Le(x)-PC-QDs) in quantitative yield as monitored by direct matrix-assisted laser desorption ionization time-of-flight mass spectrometry analyses. Live animal imaging uncovered for the first time that Le(x)-PC-QDs also distributed rapidly in the liver after intravenous injection and almost quenched over 1 h in similar profiles to those of LacNAc-PC-QDs and Lac-PC-QDs. On the other hand, sialyl LacNAc-PC-QDs and sialyl Le(x)-PC-QDs were still retained stably in the whole body after 2 h, while they showed significantly different in vivo dynamics in the tissue distribution, suggesting that structure/sequence of the neighboring sugar residues in the individual sialyl oligosaccharides might influence the final organ-specific distribution. The present results clearly visualize the evidence of an essential role of the terminal sialic acid residue(s) for achieving prolonged in vivo lifetime and biodistribution of various glyco-PC-QDs as a novel class of functional platforms for nanomaterial-based drug targeting/delivery. A standardized protocol using multifunctional PC-QDs should facilitate live animal imaging of ligand-displayed QDs using versatile NIR fluorescence photometry without influence of size-dependent accumulation/excretion pathway for nanoparticles (e.g., viruses) >10 nm in hydrodynamic diameter by the liver.