2,3-Dicyano-1-hydroxy-4-<4-(1-imidazoyl)butoxy>phenyl β-D-galactopyranoside 2',3',4',6'-tetra-O-acetate | 129786-44-3

• 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: 2,3-Dicyano-1-hydroxy-4-<4-(1-imidazoyl)butoxy>phenyl β-D-galactopyranoside 2',3',4',6'-tetra-O-acetate
• 英文别名: [(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[2,3-dicyano-4-(4-imidazol-1-ylbutoxy)phenoxy]oxan-2-yl]methyl acetate
• CAS: 129786-44-3
• 化学式: C₂₉H₃₂N₄O₁₁
• 分子量: 612.593
• InChiKey: MXTFZMJOWCECIA-JYJZCUDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.95
• 重原子数：
  44.0
• 可旋转键数：
  13.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  198.29
• 氢给体数：
  0.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  2,3-Dicyano-1-hydroxy-4-<4-(1-imidazoyl)butoxy>phenyl β-D-galactopyranoside 2',3',4',6'-tetra-O-acetate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以60%的产率得到2,3-Dicyano-1-hydroxy-4-<4-(1-imidazoyl)butoxy>phenyl β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis and characterization of a novel lysosomotropic enzyme substrate that fluoresces at intracellular pH

  摘要：

  Fluorogenic substrates that can be used to detect the activity of enzymes within intact cells are needed for biochemical investigations of human lysosomal storage disorders and identification of gene transfer recombinants. The first member of a new series of lysosomotropic fluorescent probes has been synthesized and characterized. This compound, O-[4-(1-imidazolyl)butyl]-2,3-dicyano-1,4-hydroquinonyl beta-D-galactopyranoside (Im-DCH-beta-Gal), and its aglycon, Im-DCH, contain an N-alkylimidazole as a lysosomotropic substituent. The concentration of such moderately basic amines within acidic cellular organelles should provide increased specificity toward lysosomal hydrolases. The physiochemical properties of Im-DCH, in particular the intensity of its fluorescence at acidic pH's, make its glycosides well suited for the measurement of enzymatic activity within intact cells.

  DOI：

  10.1021/jo00001a008
• 作为产物：
  描述：

  2,3-Dicyano-4-<4-(1-imidazoyl)butoxy>phenol tetrabutylammonium salt 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃糖溴化物 在 3 A molecular sieve 、 silver carbonate 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以53%的产率得到2,3-Dicyano-1-hydroxy-4-<4-(1-imidazoyl)butoxy>phenyl β-D-galactopyranoside 2',3',4',6'-tetra-O-acetate
  参考文献：
  名称：

  Synthesis and characterization of a novel lysosomotropic enzyme substrate that fluoresces at intracellular pH

  摘要：

  Fluorogenic substrates that can be used to detect the activity of enzymes within intact cells are needed for biochemical investigations of human lysosomal storage disorders and identification of gene transfer recombinants. The first member of a new series of lysosomotropic fluorescent probes has been synthesized and characterized. This compound, O-[4-(1-imidazolyl)butyl]-2,3-dicyano-1,4-hydroquinonyl beta-D-galactopyranoside (Im-DCH-beta-Gal), and its aglycon, Im-DCH, contain an N-alkylimidazole as a lysosomotropic substituent. The concentration of such moderately basic amines within acidic cellular organelles should provide increased specificity toward lysosomal hydrolases. The physiochemical properties of Im-DCH, in particular the intensity of its fluorescence at acidic pH's, make its glycosides well suited for the measurement of enzymatic activity within intact cells.

  DOI：

  10.1021/jo00001a008

文献信息

• MILLER, STEPHEN P. F.;FRENCH, STEPHANIE A.;KANESKI, CHRISTINE R., J. ORG. CHEM., 56,(1991) N, C. 30-34
  作者：MILLER, STEPHEN P. F.、FRENCH, STEPHANIE A.、KANESKI, CHRISTINE R.

  DOI：——

  日期：——