uridine-5'-diphospho-5-deoxy-D-galactofuranose | 1346254-09-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷酸
• 英文名称: uridine-5'-diphospho-5-deoxy-D-galactofuranose
• 英文别名: [(2R,3R,4R,5S)-3,4-dihydroxy-5-(2-hydroxyethyl)oxolan-2-yl] [[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] hydrogen phosphate
• CAS: 1346254-09-8
• 化学式: C₁₅H₂₄N₂O₁₆P₂
• 分子量: 550.307
• InChiKey: VYNFAFMUBLVLGA-RTXATJJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.2
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  271
• 氢给体数：
  8
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  尿苷(5')二氢二磷酰(1)-alpha-D-葡萄糖 、 [(2R,3R,4R,5S)-3,4-dihydroxy-5-(2-hydroxyethyl)oxolan-2-yl] dihydrogen phosphate 、 尿苷-5'-三磷酸 在 无机焦磷酸酶 、 UDP-glucose pyrophosphorylase 、 galactose-1-phosphate uridyltransferase 作用下， 以71%的产率得到uridine-5'-diphospho-5-deoxy-D-galactofuranose
  参考文献：
  名称：

  Synthetic UDP-Furanoses as Potent Inhibitors of Mycobacterial Galactan Biogenesis

  摘要：

  UDP-galactofuranose (UDP-Galf) is a substrate for two types of enzymes, UDP-galactopyranose mutase and galactofuranosyltransferases, which are present in many pathogenic organisms but absent from mammals. In particular, these enzymes are involved in the biosynthesis of cell wall galactan, a polymer essential for the survival of the causative agent of tuberculosis, Mycobacterium tuberculosis. We describe here the synthesis of derivatives of UDP-Galf modified at C-5 and C-6 using a chemoenzymatic route. In cell-free assays, these compounds prevented the formation of mycobacterial galactan, via the production of short "dead-end" intermediates resulting from their incorporation into the growing oligosaccharide chain. Modified UDP-furanoses thus constitute novel probes for the study of the two classes of enzymes involved in mycobacterial galactan assembly, and studies with these compounds may ultimately facilitate the future development of new therapeutic agents against tuberculosis.

  DOI：

  10.1016/j.chembiol.2010.10.014

文献信息

• 10.1016/s0076-6879(10)78019-8
  作者：Poulin, Myles B.、Lowary, Todd L.

  DOI：10.1016/s0076-6879(10)78019-8

  日期：——
• Synthetic UDP-Furanoses as Potent Inhibitors of Mycobacterial Galactan Biogenesis
  作者：Pauline Peltier、Martina Beláňová、Petronela Dianišková、Ruokun Zhou、Ruixiang Blake Zheng、Jean A. Pearcey、Maju Joe、Patrick J. Brennan、Caroline Nugier-Chauvin、Vincent Ferrières、Todd L. Lowary、Richard Daniellou、Katarína Mikušová

  DOI：10.1016/j.chembiol.2010.10.014

  日期：2010.12

  UDP-galactofuranose (UDP-Galf) is a substrate for two types of enzymes, UDP-galactopyranose mutase and galactofuranosyltransferases, which are present in many pathogenic organisms but absent from mammals. In particular, these enzymes are involved in the biosynthesis of cell wall galactan, a polymer essential for the survival of the causative agent of tuberculosis, Mycobacterium tuberculosis. We describe here the synthesis of derivatives of UDP-Galf modified at C-5 and C-6 using a chemoenzymatic route. In cell-free assays, these compounds prevented the formation of mycobacterial galactan, via the production of short "dead-end" intermediates resulting from their incorporation into the growing oligosaccharide chain. Modified UDP-furanoses thus constitute novel probes for the study of the two classes of enzymes involved in mycobacterial galactan assembly, and studies with these compounds may ultimately facilitate the future development of new therapeutic agents against tuberculosis.