uridine-5'-(2-isobutyramido-2-deoxy-α-D-glucopyranosyl diphosphate)

• 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-isobutyramido-2-deoxy-α-D-glucopyranosyl diphosphate)
• 英文别名: UDP-N-isobutyrylglucosamine；[(2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-(2-methylpropanoylamino)oxan-2-yl] [[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] hydrogen phosphate
• 化学式: C₁₉H₃₁N₃O₁₇P₂
• 分子量: 635.413
• InChiKey: QWDYNIIQYFWDCJ-WFDMZIERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.6
• 重原子数：
  41
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  300
• 氢给体数：
  9
• 氢受体数：
  17

反应信息

• 作为产物：
  描述：

  D-氨基葡萄糖-1-磷酸 在 氢氧化钾 、 Dowex 50-X₈ triethylammonium form 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 120.0h， 生成 uridine-5'-(2-isobutyramido-2-deoxy-α-D-glucopyranosyl diphosphate)
  参考文献：
  名称：

  Artificial N-functionalized UDP-glucosamine analogues as modified substrates for N-acetylglucosaminyl transferases

  摘要：

  Analogues of UDP-GlcNAc modified at the 2-acetamido group of the GlcNAc moiety were prepared in order to study their role in the mechanism of N-acetylglucosaminyl transferase mediated glycosylation reactions. The structural analogues with N-formyl-, N-propionyl-, N-butyryl- and N-isobutyryl-groups were synthesized, utilizing the morpholidate coupling method starting from D-glucosaminyl-1-phosphate after selective N-acylation of its amino group with the appropriate N-acyloxysuccinimide esters as well as a chlorinated formylformiate. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.01.017

文献信息

• Artificial N-functionalized UDP-glucosamine analogues as modified substrates for N-acetylglucosaminyl transferases
  作者：Daniel Lazarević、Joachim Thiem

  DOI：10.1016/j.carres.2006.01.017

  日期：2006.4

  Analogues of UDP-GlcNAc modified at the 2-acetamido group of the GlcNAc moiety were prepared in order to study their role in the mechanism of N-acetylglucosaminyl transferase mediated glycosylation reactions. The structural analogues with N-formyl-, N-propionyl-, N-butyryl- and N-isobutyryl-groups were synthesized, utilizing the morpholidate coupling method starting from D-glucosaminyl-1-phosphate after selective N-acylation of its amino group with the appropriate N-acyloxysuccinimide esters as well as a chlorinated formylformiate. (c) 2006 Elsevier Ltd. All rights reserved.