p-Aminophenyl 2-acetamido-2-deoxy-4-O-β-D-galactopyranosyl-β-D-glucopyranoside | 157383-90-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-Aminophenyl 2-acetamido-2-deoxy-4-O-β-D-galactopyranosyl-β-D-glucopyranoside
• 英文别名: Gal(b1-4)GlcNAc(b)-O-Ph(4-NH2)；N-[(2S,3R,4R,5S,6R)-2-(4-aminophenoxy)-4-hydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]acetamide
• CAS: 157383-90-9
• 化学式: C₂₀H₃₀N₂O₁₁
• 分子量: 474.465
• InChiKey: MNRUSHUEZPFLBJ-KDKNCOTBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.1
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  213
• 氢给体数：
  8
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  p-Aminophenyl 2-acetamido-2-deoxy-4-O-β-D-galactopyranosyl-β-D-glucopyranoside 在 苯磺酰胺 、 manganese(ll) chloride O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三乙胺 、 alkaline phosphatase 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 [(6-biotinylamido)hexanoylamido]-phenyl 5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-nonulosyl-2-onic acid-(2->3)-β-D-galactopyranoside-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Effective chemoenzymatic synthesis of p-aminophenyl glycosides of sialyl N-acetyllactosaminide and analysis of their interactions with lectins

  摘要：

  A convenient chemoenzymatic procedure for the synthesis of p-aminophenyl glycosides of sialyl N-acetyllactosaminide has been developed from p-nitrophenyl N-acetyl-beta-D-glucosaminide as starting material through three steps: synthesis of p-nitrophenyl N-acetyllactosaminide with P-D-galactosidase, chemical reduction of the p-nitrophenyl group, and sialylation with sialyltransferase. The p-aminophenyl glycosides were then successfully biotin-labeled through the coupling with N-(+)-biotinyl-6-aminohexanoic acid to afford biotinylated oligosaccharides with an aminohexanosyl group and phenyl group as the spacers between the biotin and glycan. Furthermore, the biotin-labeled sugars were shown to be useful for immobilization and assay of the carbohydrate-lectin interactions by an optical biosensor based on surface plasmon resonance. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.03.010
• 作为产物：
  描述：

  4-硝基苯基 2-乙酰氨基-2-脱氧-4-o-(β-d-galacto吡喃osyl)-β-d-吡喃葡萄糖苷 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 以32%的产率得到p-Aminophenyl 2-acetamido-2-deoxy-4-O-β-D-galactopyranosyl-β-D-glucopyranoside
  参考文献：
  名称：

  Kobayashi, Kazukiyo; Kakishita, Naohito; Okada, Masahiko, Journal of Carbohydrate Chemistry, 1994, vol. 13, # 5, p. 753 - 766

  摘要：

  DOI：

文献信息

• Kobayashi, Kazukiyo; Kakishita, Naohito; Okada, Masahiko, Journal of Carbohydrate Chemistry, 1994, vol. 13, # 5, p. 753 - 766
  作者：Kobayashi, Kazukiyo、Kakishita, Naohito、Okada, Masahiko、Akaike, Toshihiro、Usui, Taichi

  DOI：——

  日期：——
• Effective chemoenzymatic synthesis of p-aminophenyl glycosides of sialyl N-acetyllactosaminide and analysis of their interactions with lectins
  作者：Xiaoxiong Zeng、Yi Sun、Hong Ye、Jun Liu、Xiaoli Xiang、Bei Zhou、Hirotaka Uzawa

  DOI：10.1016/j.carres.2007.03.010

  日期：2007.7

  A convenient chemoenzymatic procedure for the synthesis of p-aminophenyl glycosides of sialyl N-acetyllactosaminide has been developed from p-nitrophenyl N-acetyl-beta-D-glucosaminide as starting material through three steps: synthesis of p-nitrophenyl N-acetyllactosaminide with P-D-galactosidase, chemical reduction of the p-nitrophenyl group, and sialylation with sialyltransferase. The p-aminophenyl glycosides were then successfully biotin-labeled through the coupling with N-(+)-biotinyl-6-aminohexanoic acid to afford biotinylated oligosaccharides with an aminohexanosyl group and phenyl group as the spacers between the biotin and glycan. Furthermore, the biotin-labeled sugars were shown to be useful for immobilization and assay of the carbohydrate-lectin interactions by an optical biosensor based on surface plasmon resonance. (C) 2007 Elsevier Ltd. All rights reserved.