(2S,3R,4S,5S)-5-((R)-2-(((2S,3R,4R,5R,6R)-3-acetamido-4,5-diacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-1-acetoxyethyl)tetrahydrofuran-2,3,4-triyl triacetate | 1271737-89-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4S,5S)-5-((R)-2-(((2S,3R,4R,5R,6R)-3-acetamido-4,5-diacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-1-acetoxyethyl)tetrahydrofuran-2,3,4-triyl triacetate
• CAS: 1271737-89-3
• 化学式: C₂₈H₃₉NO₁₈
• 分子量: 677.614
• InChiKey: VJWWXUGNORMUSK-HIJMLSBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.26
• 重原子数：
  47.0
• 可旋转键数：
  13.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  240.89
• 氢给体数：
  1.0
• 氢受体数：
  18.0

反应信息

• 作为产物：
  描述：

  2-乙酰氨基-2-脱氧-D-吡喃半乳糖 、 乙酸酐 在 α-N-acetylgalactosaminidase from Aspergillus niger CCIM K2 、 吡啶 作用下， 反应 132.0h， 以0.4%的产率得到(2S,3R,4R,5R,6R)-3-acetamido-4-(((2S,3R,4R,5R,6R)-3-acetamido-4,5-diacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-6-(acetoxymethyl)tetrahydro-2H-pyran-2,5-diyl diacetate
  参考文献：
  名称：

  Condensation reactions catalyzed by α-N-acetylgalactosaminidase fromAspergillus nigeryielding α-N-acetylgalactosaminides

  摘要：

  Extracellular alpha-N-acetylgalactosaminidase from Aspergillus niger catalyzed glycosylation yielding a series of 2-acetamido-2-deoxy-alpha-D-galactobiosides using 2-acetamido-2-deoxy-D-galactopyranose as a glycosyl donor. The isomers alpha-D-GalpNAc-(1 -> 6)-D-GalpNAc, alpha-D-GalpNAc-(1 -> 3)-D-GalpNAc and alpha-D-GalpNAc-(1 -> 6)-D-GalfNAc were isolated and spectrally characterized. The purified enzyme was further used for the glycosylation of free amino acids (serine and threonine) and their N-(tert-butoxycarbonyl)-protected analogs to synthesize the Tn antigen (GalpNAc-alpha-O-Ser/Thr) and its N-(tert-butoxycarbonyl)-protected derivatives.

  DOI：

  10.3109/10242421003587227