4-aminophenyl 4-S-β-D-glucopyranosyl-1,4-dithio-β-D-glucopyranoside | 116307-18-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-aminophenyl 4-S-β-D-glucopyranosyl-1,4-dithio-β-D-glucopyranoside
• 英文别名: (2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6S)-6-(4-aminophenyl)sulfanyl-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]sulfanyl-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 116307-18-7
• 化学式: C₁₈H₂₇NO₉S₂
• 分子量: 465.546
• InChiKey: MSXOBUOPIRAMCR-BYKNIKRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  237
• 氢给体数：
  8
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  4-氨基苯硫酚 在 sodium methylate 、 potassium carbonate 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 生成 4-aminophenyl 4-S-β-D-glucopyranosyl-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

文献信息

• 4-Thiocellooligosaccharides. Their synthesis and use as ligands for the separation of cellobiohydrolases of Trichoderma reesei by affinity chromatography
  作者：Catherine Orgeret、Elizabeth Seillier、Catherine Gautier、Jacques Defaye、Hugues Driguez

  DOI：10.1016/0008-6215(92)84090-f

  日期：1992.2

  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.