1,2,3,6-tetra-O-acetyl-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-β-D-galactopyranosyl)-β-D-glucopyranose | 190973-75-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,2,3,6-tetra-O-acetyl-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-β-D-galactopyranosyl)-β-D-glucopyranose
• CAS: 190973-75-2
• 化学式: C₂₆H₃₅FO₁₇
• 分子量: 638.552
• InChiKey: OJMMGDOFJXMHEJ-BYYXLUDDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.42
• 重原子数：
  44.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  211.79
• 氢给体数：
  0.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  1,2,3,6-tetra-O-acetyl-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-β-D-galactopyranosyl)-β-D-glucopyranose 在 sodium methylate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以88%的产率得到4-O-(2-deoxy-2-fluoro-β-D-galactopyranosyl)-D-glucopyranose
  参考文献：
  名称：

  Design and Synthesis of 2‘-Deoxy-2‘-Fluorodisaccharides as Mechanism-Based Glycosidase Inhibitors That Exploit Aglycon Specificity

  摘要：

  Stable, aglycon-specific inactivators of glycosidases have considerable potential as fools in the study of mechanisms of oligosaccharide processing, and possibly as avenues toward new therapeutics. Glycosidases for which the rate-determining step with the natural substrate is the hydrolysis of the glycosyl-enzyme intermediate are shown to be inactivated by the 2'-deoxy-2'-fluoro derivative of this substrate. Thus Agrobacterium faecalis beta-glucosidase is inactivated by 2'-deoxy-2'-fluorocellobiose according to inactivation parameters of k(i) = 0.018 min(-1) and K-i = 20 mM. Inactivation is shown to occur via the accumulation of the same 2-deoxy-2-fluoroglycosyl-enzyme intermediate as that formed using activated 2-deoxy-2-fluoroglycosides by identification of the labeled peptide in proteolytic digests. Thus, interactions between the enzyme and the sugar aglycon provide sufficient transition state stabilization to allow formation and trapping of the glycosyl-enzyme. beta-Glucocerebrosidase, a beta-glucosidase specific for hydrolysis of glucocerebrosides, is not inactivated by 2'-deoxy-2'-fluorocellobiose, thereby demonstrating the aglycon specificity of this class of inactivator.

  DOI：

  10.1021/ja9627454
• 作为产物：
  描述：

  2,3-di-O-acetyl-1,6-anhydro-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-D-galactopyranosyl)-β-D-glucopyranose 在 氢溴酸 、 氢气 、 溶剂黄146 作用下， 以 乙酸酐 为溶剂， 反应 2.5h， 生成 1,2,3,6-tetra-O-acetyl-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-β-D-galactopyranosyl)-β-D-glucopyranose
  参考文献：
  名称：

  Design and Synthesis of 2‘-Deoxy-2‘-Fluorodisaccharides as Mechanism-Based Glycosidase Inhibitors That Exploit Aglycon Specificity

  摘要：

  Stable, aglycon-specific inactivators of glycosidases have considerable potential as fools in the study of mechanisms of oligosaccharide processing, and possibly as avenues toward new therapeutics. Glycosidases for which the rate-determining step with the natural substrate is the hydrolysis of the glycosyl-enzyme intermediate are shown to be inactivated by the 2'-deoxy-2'-fluoro derivative of this substrate. Thus Agrobacterium faecalis beta-glucosidase is inactivated by 2'-deoxy-2'-fluorocellobiose according to inactivation parameters of k(i) = 0.018 min(-1) and K-i = 20 mM. Inactivation is shown to occur via the accumulation of the same 2-deoxy-2-fluoroglycosyl-enzyme intermediate as that formed using activated 2-deoxy-2-fluoroglycosides by identification of the labeled peptide in proteolytic digests. Thus, interactions between the enzyme and the sugar aglycon provide sufficient transition state stabilization to allow formation and trapping of the glycosyl-enzyme. beta-Glucocerebrosidase, a beta-glucosidase specific for hydrolysis of glucocerebrosides, is not inactivated by 2'-deoxy-2'-fluorocellobiose, thereby demonstrating the aglycon specificity of this class of inactivator.

  DOI：

  10.1021/ja9627454