uridine 5'-diphospho-α-D-fucofuranose | 1000874-38-3

• 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-α-D-fucofuranose
• 英文别名: uridine-5'-diphospho-6-deoxy-D-galactofuranose；UDP-α-D-Fucf；UDP-fucofuranose；[(2R,3R,4R,5S)-3,4-dihydroxy-5-[(1R)-1-hydroxyethyl]oxolan-2-yl] [[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] hydrogen phosphate
• CAS: 1000874-38-3
• 化学式: C₁₅H₂₄N₂O₁₆P₂
• 分子量: 550.307
• InChiKey: RYQDVONYCXFOMC-SIAUPFDVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.6
• 重原子数：
  35
• 可旋转键数：
  9
• 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：

  ammonium D-fucofuranosyl 1-phosphate 、 sodium,[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl [hydroxy-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphosphoryl] phosphate 在 无机焦磷酸酶 、 galactose-1-phosphate uridylyltransferase 、 UDP-glucose pyrophosphorylase 、 uridine 5'-triphosphate trisodium salt 作用下， 反应 24.0h， 以12%的产率得到uridine 5'-diphospho-α-D-fucofuranose
  参考文献：
  名称：

  从 α,β-呋喃糖基 1-磷酸酯立体选择性化学酶法合成 UDP-1,2-顺式呋喃糖

  摘要：

  含呋喃糖基的糖缀合物的生物合成描述甚少，主要是由于缺乏 UDP-呋喃糖。在这里，我们展示了我们在多酶系统的帮助下合成稀有核苷酸糖的努力，特别是包括 1-磷酸半乳糖尿苷转移酶。首先，STD-NMR 技术被用来探测这种特定酶的广泛底物特异性。然后用未保护的硫亚氨基供体进行所需的呋喃糖基 1-磷酸起始材料的化学合成。这导致了 UDP-β-L-阿拉伯呋喃糖、UDP-α-D-岩藻呋喃糖和 UDP-α-D-6F-呋喃半乳糖的首次立体选择性化学酶促合成。 （© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  DOI：

  10.1002/ejoc.200800742

文献信息

• 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.
• 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：——