methyl 6-azido-6-deoxy-β-lactoside | 147664-44-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-azido-6-deoxy-β-lactoside
• CAS: 147664-44-6
• 化学式: C₁₃H₂₃N₃O₁₀
• 分子量: 381.34
• InChiKey: QEQQFFULKMKLKB-ABBMIVAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.43
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  207.06
• 氢给体数：
  6.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  methyl 6-azido-6-deoxy-β-lactoside 在 吡啶 、 硫化氢 、 三乙胺 作用下， 反应 5.0h， 生成 methyl-6-amino-6-deoxy-β-lactoside
  参考文献：
  名称：

  The Function of the 5-Hydroxymethyl Group of Lactose in Enzymatic Hydrolysis with beta-Galactosidase from E. coli.

  摘要：

  A series of 6-substituted methyl lactoside derivatives together with methyl allolactoside and (6S)-methyl [6-H-2]lactoside have been synthesized and characterized by NMR spectroscopy. All compounds were tested as substrates for the enzyme beta-galactosidase from E. coli using progress curve kinetic methology both in single-substrate and competition experiments. The results show that the hydrolysis of methyl lactoside to a large extent takes place through an intramolecular trans-glycosidation reaction via allolactoside. Furthermore, methyl 6-amino-6-deoxy-D-glucopyranoside proved to be an inhibitor for the enzymatic hydrolysis.

  DOI：

  10.3891/acta.chem.scand.46-1114
• 作为产物：
  描述：

  1',2',3',6',2,3,4,6-octa-O-acetyl-β-D-lactose 在 吡啶 、 甲醇 、 氢氧化钾 、 sodium azide 、 氢氟酸 、 水 、 sodium methylate 、 四氯化钛 、 silver carbonate 作用下， 以 乙醇 、 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.67h， 生成 methyl 6-azido-6-deoxy-β-lactoside
  参考文献：
  名称：

  The Function of the 5-Hydroxymethyl Group of Lactose in Enzymatic Hydrolysis with beta-Galactosidase from E. coli.

  摘要：

  A series of 6-substituted methyl lactoside derivatives together with methyl allolactoside and (6S)-methyl [6-H-2]lactoside have been synthesized and characterized by NMR spectroscopy. All compounds were tested as substrates for the enzyme beta-galactosidase from E. coli using progress curve kinetic methology both in single-substrate and competition experiments. The results show that the hydrolysis of methyl lactoside to a large extent takes place through an intramolecular trans-glycosidation reaction via allolactoside. Furthermore, methyl 6-amino-6-deoxy-D-glucopyranoside proved to be an inhibitor for the enzymatic hydrolysis.

  DOI：

  10.3891/acta.chem.scand.46-1114