4-Deoxy-4-fluoro-α-D-galactopyranoside | 32934-09-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-Deoxy-4-fluoro-α-D-galactopyranoside
• 英文别名: 4-deoxy-4-fluorogalactopyranose；4-Deoxy-4-fluoro-I+/--D-galactopyranose；(2S,3R,4R,5R,6R)-5-fluoro-6-(hydroxymethyl)oxane-2,3,4-triol
• CAS: 32934-09-1
• 化学式: C₆H₁₁FO₅
• 分子量: 182.149
• InChiKey: FIHYONSINSKFAH-PHYPRBDBSA-N

物化性质

• 沸点：
  370.1±42.0 °C(Predicted)
• 密度：
  1.59±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  90.2
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  Methyl 4-deoxy-4-fluoro-6-O-trityl-α-D-galactopyranoside 在 Dowex 50W-X₈ (H(+)) 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 25.0h， 生成 4-Deoxy-4-fluoro-α-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of UDP-4-deoxy-4-fluoroglucose and UDP-4-deoxy-4-fluorogalactose and their Interactions with Enzymes of Nucleotide Sugar Metabolism

  摘要：

  Fluorinated carbohydrates can be used as probes of enzymatic active sites. We report the synthesis of 4-deoxy-4-fluoro-alpha-D-galactose-1-phosphate and the substrate analogues of UDP-galactose, UDP-4-deoxy-4-fluoro-alpha-D-galactose (UDP-FGal), and of UDP-glucose, UDP-4-deoxy-4-fluoro-alpha-D-glucose (UDP-FGlc), which may be useful in analyzing the binding properties of enzymes that utilize nucleotide sugars as substrates. As a first step in this study, we determine the kinetic and inhibition parameters for UDP-FGal and UDP-FGlc interacting with UDP-glucose dehydrogenase and UDP-galactose 4-epimerase. UDP-FGlc is a substrate for bovine liver UDP-glucose dehydrogenase: K-m = 30.2 +/- 4.5 mu M slightly higher than the value 9.6 +/- 0.7 mu M for UDP-glucose, and V-mUDP-FGlc = 046V (mUDP-Glc). UDP-FGal is not a substrate for UDP-glucose dehydrogenase but is a competitive inhibitor with respect to UDP-glucose (K-i = 19.9 +/- 6.6 mu M). These analogs also bind to UDP-galactose 4-epimerase from E. coli with dissociation constants K-d of 1.4 and 1.1 mM for UDP-FGlc and UDP-FGal, respectively.

  DOI：

  10.1021/jo00102a024