O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-N-(tert-butoxycarbonyl)-L-serine | 167688-31-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-N-(tert-butoxycarbonyl)-L-serine
• CAS: 167688-31-5
• 化学式: C₁₆H₂₈N₂O₁₀
• 分子量: 408.406
• InChiKey: AWVSJDTTZYPZLC-ZVBWPKDRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.08
• 重原子数：
  28.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  183.88
• 氢给体数：
  6.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-N-(tert-butoxycarbonyl)-L-serine 以7.4%的产率得到O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-serine
  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
• 作为产物：
  描述：

  2-乙酰氨基-2-脱氧-D-吡喃半乳糖 、 BOC-L-丝氨酸 在 α-N-acetylgalactosaminidase from Aspergillus niger CCIM K2 作用下， 反应 240.0h， 生成 O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-N-(tert-butoxycarbonyl)-L-serine
  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