uridine 5'-(2-deoxy-2-fluoro-α-D-galactopyranosyl diphosphate) | 118694-15-8

• 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'-(2-deoxy-2-fluoro-α-D-galactopyranosyl diphosphate)
• 英文别名: uridine-5'-diphosphate-2-deoxy-2-fluorogalactose；uridine 5'-diphospho-2-deoxy-2-fluoro-α-D-galactose；[[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3R,4S,5R,6R)-3-fluoro-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl] hydrogen phosphate
• CAS: 118694-15-8
• 化学式: C₁₅H₂₃FN₂O₁₆P₂
• 分子量: 568.297
• InChiKey: NGTCPFGWXMBZEP-KBQKSTHMSA-N

物化性质

• 密度：
  1.93±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -5.6
• 重原子数：
  36
• 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：
  17

反应信息

• 作为反应物：
  描述：

  uridine 5'-(2-deoxy-2-fluoro-α-D-galactopyranosyl diphosphate) 在 UDP-galactopyranose mutase 、 腺嘌呤黄素 、 1,4-二巯基-2,3-丁二醇 作用下， 生成
  参考文献：
  名称：

  Enzymatic synthesis of UDP-(3-deoxy-3-fluoro)-d-galactose and UDP-(2-deoxy-2-fluoro)-d-galactose and substrate activity with UDP-galactopyranose mutase

  摘要：

  The novel UDP-sugar uridine 5'-(3-deoxy-3-fluoro-D-galactopyranosyl diphosphate) (I) and UDP-(2-deoxy-2-fluoro)-D-galactose (2) have been prepared enzymatically and tested as substrate analogues for the enzyme UDP-galactopyranose mutase (UDP-Galp mutase EC 5.4.99.9). Turnover of both 1 and 2 by UDP-Galp mutase was observed by HPLC and F-19 NMR. The HPLC elution profile and F-19 chemical shift of the products are consistent with the formation of the predicted furanose forms of 1 and 2. The K-m values for compounds 1 and 2 were similar to those of the natural substrate UDP-Galp (0.26 mM for 1, 0.2 mM for 2, and 0.6 mM for UDP-Galp), but the values for k(cat) were substantially different (1.6/min for I, 0.02/min for 2, and 1364/min for UDP-Galp). A correlation was also observed between the equilibrium yield of product formed during turnover of UDP-sugar by UDP-Galp mutase (UDP-Galp, compound 1 or compound 2), and the amount of furanose present for the free sugar at thermal equilibrium in aqueous solution, using H-1 and F-19 NMR spectroscopy. The implications of these results to the mechanism of the unusual enzymatic reaction are discussed. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00135-x
• 作为产物：
  描述：

  2-deoxy-2-fluoro-D-galactose 在 氢氧化钾 、 2(1H)-喹啉酮,1-丙基- 、 pyruvate kinase 、 无机焦磷酸酶 、 DL-半胱氨酸 、 galactose-1-phosphate uridyl transferase 、 HEPES buffer 、 uridine-5'-diphosphoglucose pyrophosphorylase 、 potassium chloride 、 phosphoenolpyruvate trisodium salt 、 uridine 5'-triphosphate trisodium salt 、 adenosine 5'-triphosphate disodium salt 、 magnesium chloride 、 manganese(ll) chloride 、 1,4-二巯基-2,3-丁二醇 作用下， 反应 168.0h， 生成 uridine 5'-(2-deoxy-2-fluoro-α-D-galactopyranosyl diphosphate)
  参考文献：
  名称：

  UDP-（2-脱氧-2-氟）-半乳糖的化学酶法合成及其与半乳糖基转移酶的相互作用的评估。

  摘要：

  发现尿苷5'-二磷酸-（2-脱氧-2-氟）半乳糖（UDP-2FGal）首次通过化学酶法制备和鉴定，是竞争性的β-1,4-半乳糖基转移酶抑制剂，具有Ki值为149 microM。这项研究支持糖基转移酶反应机制通过在异头中心形成的具有sp2特征的糖苷裂解过渡态来进行。

  DOI：

  10.1016/s0968-0896(96)00263-5

文献信息

• A chemoenzymatic synthesis of UDP-(2-deoxy-2-fluoro)galactose and evaluation of its interaction with galactosyltransferase
  作者：Takashi Hayashi、Brion W Murray、Ruo Wang、Chi-Huey Wong

  DOI：10.1016/s0968-0896(96)00263-5

  日期：1997.3

  Uridine 5'-diphospho-(2-deoxy-2-fluoro)galactose (UDP-2FGal), prepared and characterized for the first time by a chemoenzymatic method, was found to be a competitive inhibitor of beta-1,4-galactosyltransferase with a Ki value of 149 microM. This study supports that the glycosyltransferase reaction mechanism proceeds through a glycosidic cleavage transition state with sp2 character developed at the

  发现尿苷5'-二磷酸-（2-脱氧-2-氟）半乳糖（UDP-2FGal）首次通过化学酶法制备和鉴定，是竞争性的β-1,4-半乳糖基转移酶抑制剂，具有Ki值为149 microM。这项研究支持糖基转移酶反应机制通过在异头中心形成的具有sp2特征的糖苷裂解过渡态来进行。
• Enzymatic synthesis of UDP-(3-deoxy-3-fluoro)-d-galactose and UDP-(2-deoxy-2-fluoro)-d-galactose and substrate activity with UDP-galactopyranose mutase
  作者：John N. Barlow、John S. Blanchard

  DOI：10.1016/s0008-6215(00)00135-x

  日期：2000.10

  The novel UDP-sugar uridine 5'-(3-deoxy-3-fluoro-D-galactopyranosyl diphosphate) (I) and UDP-(2-deoxy-2-fluoro)-D-galactose (2) have been prepared enzymatically and tested as substrate analogues for the enzyme UDP-galactopyranose mutase (UDP-Galp mutase EC 5.4.99.9). Turnover of both 1 and 2 by UDP-Galp mutase was observed by HPLC and F-19 NMR. The HPLC elution profile and F-19 chemical shift of the products are consistent with the formation of the predicted furanose forms of 1 and 2. The K-m values for compounds 1 and 2 were similar to those of the natural substrate UDP-Galp (0.26 mM for 1, 0.2 mM for 2, and 0.6 mM for UDP-Galp), but the values for k(cat) were substantially different (1.6/min for I, 0.02/min for 2, and 1364/min for UDP-Galp). A correlation was also observed between the equilibrium yield of product formed during turnover of UDP-sugar by UDP-Galp mutase (UDP-Galp, compound 1 or compound 2), and the amount of furanose present for the free sugar at thermal equilibrium in aqueous solution, using H-1 and F-19 NMR spectroscopy. The implications of these results to the mechanism of the unusual enzymatic reaction are discussed. (C) 2000 Elsevier Science Ltd. All rights reserved.