4-aminophenyl S-β-D-glucopyranosyl-(1->4)-S-4-thio-β-D-glucopyranosyl-(1->4)-1,4-dithio-β-D-glucopyranoside | 116307-19-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-aminophenyl S-β-D-glucopyranosyl-(1->4)-S-4-thio-β-D-glucopyranosyl-(1->4)-1,4-dithio-β-D-glucopyranoside
• CAS: 116307-19-8
• 化学式: C₂₄H₃₇NO₁₃S₃
• 分子量: 643.755
• InChiKey: LYEWPYLHDSWMQM-FVLBVTBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.76
• 重原子数：
  41.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  256.01
• 氢给体数：
  11.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 4-aminophenyl S-β-D-glucopyranosyl-(1->4)-S-4-thio-β-D-glucopyranosyl-(1->4)-1,4-dithio-β-D-glucopyranoside 在 吡啶 作用下， 以87%的产率得到4-acetamidophenyl S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->4)-S-(2,3,6-tri-O-acetyl-4-thio-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-1,4-dithio-β-D-glucopyranoside
  参考文献：
  名称：

  4-Thiocellooligosaccharides. Their synthesis and use as ligands for the separation of cellobiohydrolases of Trichoderma reesei by affinity chromatography

  摘要：

  4-Aminophenyl 1,4-dithio-beta-cellobioside (6) was obtained by treatment of methyl 2,3,6-tri-O-benzoyl-4-O-triflyl-alpha-D-galactopyranoside with the sodium salt of 1-thio-beta-D-glucopyranose, followed by acetolysis and glycosylation of the corresponding bromide with 4-aminobenzenethiol and subsequent deacylation. A similar synthesis starting with the 1-thiolate of 1,4-dithio-beta-cellobiose led to the trisaccharide 4-aminophenyl 1,4,4'-trithiocellotrioside (16). The 4-acetamidophenyl di- and tri-thiocellooligosaccharides were found to be excellent competitive inhibitors of the hydrolysis of 4-methylumbelliferyl beta-lactoside with respective K(i) values of 25 and 6.5mM. The two 4-aminophenyl oligosaccharides 6 and 16 were coupled to CH-Sepharose 4B, and the affinity gels were used for the purification of cellobiohydrolases from a crude commercial cellulolytic extract of T. reesei. Cellobiohydrolases I or II were selectively desorbed from gels bearing ligands 6 and 16.

  DOI：

  10.1016/0008-6215(92)84090-f
• 作为产物：
  描述：

  在 potassium carbonate 作用下， 以 水 、 丙酮 为溶剂， 生成 4-aminophenyl S-β-D-glucopyranosyl-(1->4)-S-4-thio-β-D-glucopyranosyl-(1->4)-1,4-dithio-β-D-glucopyranoside
  参考文献：
  名称：

  4-Thiocellooligosaccharides. Their synthesis and use as ligands for the separation of cellobiohydrolases of Trichoderma reesei by affinity chromatography

  摘要：

  4-Aminophenyl 1,4-dithio-beta-cellobioside (6) was obtained by treatment of methyl 2,3,6-tri-O-benzoyl-4-O-triflyl-alpha-D-galactopyranoside with the sodium salt of 1-thio-beta-D-glucopyranose, followed by acetolysis and glycosylation of the corresponding bromide with 4-aminobenzenethiol and subsequent deacylation. A similar synthesis starting with the 1-thiolate of 1,4-dithio-beta-cellobiose led to the trisaccharide 4-aminophenyl 1,4,4'-trithiocellotrioside (16). The 4-acetamidophenyl di- and tri-thiocellooligosaccharides were found to be excellent competitive inhibitors of the hydrolysis of 4-methylumbelliferyl beta-lactoside with respective K(i) values of 25 and 6.5mM. The two 4-aminophenyl oligosaccharides 6 and 16 were coupled to CH-Sepharose 4B, and the affinity gels were used for the purification of cellobiohydrolases from a crude commercial cellulolytic extract of T. reesei. Cellobiohydrolases I or II were selectively desorbed from gels bearing ligands 6 and 16.

  DOI：

  10.1016/0008-6215(92)84090-f