4-aminophenyl 3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-glucopyranoside | 65907-85-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-aminophenyl 3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-glucopyranoside
• 英文别名: p-aminophenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-O-β-D-glucopyranoside；(4-amino-phenyl)-(tri-O-acetyl-2-acetylamino-2-deoxy-β-D-glucopyranoside)；(4-Amino-phenyl)-(tri-O-acetyl-2-acetylamino-2-desoxy-β-D-glucopyranosid)；[(2R,3S,4R,5R,6S)-5-acetamido-3,4-diacetyloxy-6-(4-aminophenoxy)oxan-2-yl]methyl acetate
• CAS: 65907-85-9
• 化学式: C₂₀H₂₆N₂O₉
• 分子量: 438.434
• InChiKey: UGWNRSZZWMHTMU-LASHMREHSA-N

物化性质

• 沸点：
  635.4±55.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  31
• 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：
  153
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  4-aminophenyl 3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 、 氯仿 、 乙腈 为溶剂， 反应 1.0h， 以61.8%的产率得到4-氨基苯基2-乙酰氨基-2-脱氧吡喃己糖苷
  参考文献：
  名称：

  Synthesis of 4-Aminophenyl N-Acetyl-.BETA.-D-glucosaminide Derivatives and Their Application to the Rate-Assay of N-Acetyl-.BETA.-D-glucosaminidase.

  摘要：

  合成了四种 N-乙酰基-β-D-氨基葡萄糖苷，即 4-氨基-2，6-二溴苯基（1a）、4-氨基-2，6-二氯苯基（1b）、4-氨基-2-氯苯基（1c）和 4-氨基苯基 N-乙酰基-β-D-氨基葡萄糖苷（1d）。底物 1a-c 被 N-乙酰基-β-D-葡糖苷酶水解，释放出的苷元与 N-乙基-N-（3-甲基苯基）-N'-丁二酰乙二胺反应，在胆红素氧化酶存在下，在弱酸性速率测定条件（pH 5.0）下生成吲哚苯胺染料。1a-c 的 Km 值分别为 1.97、1.65 和 1.39 mM。在这些化合物中，1b 被认为是最有潜力用于 N-乙酰基-β-D-葡萄糖苷酶速率测定的底物，因为它在酶水解和偶联反应后显示出最大的 Vmax 值和最强的从无色到绿色的颜色生成（λmax 302→718 nm）。此外，1b 在水溶液中具有中等溶解度和稳定性，对酶的敏感性比 2-氯-4-硝基苯基 N-乙酰基-β-D-氨基葡萄糖苷高约 5.9 倍。

  DOI：

  10.1248/cpb.43.266
• 作为产物：
  描述：

  对硝基苯酚 在 palladium on activated charcoal sodium hydroxide 、 四丁基硫酸氢铵 、 ammonium formate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.08h， 生成 4-aminophenyl 3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Syntheses and transformations of glycohydrolase substrates into protein conjugates based on Michael additions

  摘要：

  通过相转移催化，糖基氯化物 1 和溴化物 2 及 3 被立体定向转化为对硝基苯基糖苷；这些糖水解酶底物被还原和 N-丙烯酰化，从而产生迈克尔受体，与蛋白质的胺功能发生反应。

  DOI：

  10.1039/c39910000536

文献信息

• Glycosylated tris-bipyridine ferrous complexes to provide dynamic combinatorial libraries for probing carbohydrate–carbohydrate interactions
  作者：Motomi Nakamura、Mayuka Tsutsumi、Yoshiaki Ishikawa、Haruka Umemiya、Toki Hasegawa、Kazumi Izawa、Haruka Abe、Yosuke Togashi、Tatsuya Kinone、Sho Sekiguchi、Mihiro Igumi、Kanako Ide、Teruaki Hasegawa

  DOI：10.1016/j.tet.2013.01.095

  日期：2013.4

  2,2-Bipyridines having beta-lactoside, beta-D-glucoside, beta-D-galactoside, and N-acetyl-beta-D-glucosaminide were prepared and then, complexed with ferrous ion to afford trivalent glycoclusters having tris-bipyridine ferrous complex cores. Each glycocluster provides a dynamic combinatorial library composed of four diastereomeric stereoisomers (Delta mer, Delta fac, Delta mer, and Delta fac) whose ratios depend on their relative stabilities. CD spectral analyses of these glycoclusters showed that various cations (Na+, Mg2+, K+ or Ca2+) enriched Delta-forms of the glycocluster having beta-lactosides and N-acetyl-beta-D-glucosaminides possibly by cations-induced intramolecular carbohydrate-carbohydrate interactions. (C) 2013 Elsevier Ltd. All rights reserved.
• Westphal; Schmidt, Justus Liebigs Annalen der Chemie, 1952, vol. 575, p. 84,89
  作者：Westphal、Schmidt

  DOI：——

  日期：——
• Roy, Rene; Tropper, Francois D., Canadian Journal of Chemistry, 1991, vol. 69, # 5, p. 817 - 821
  作者：Roy, Rene、Tropper, Francois D.

  DOI：——

  日期：——
• WO2020010090A5
  申请人：——

  公开号：WO2020010090A5

  公开（公告）日：2022-03-16
• 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.