2-deoxy-2-propionylamido-α-D-glucopyranosyl phosphate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-deoxy-2-propionylamido-α-D-glucopyranosyl phosphate
• 英文别名: [(2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-(propanoylamino)oxan-2-yl] dihydrogen phosphate
• 化学式: C₉H₁₈NO₉P
• 分子量: 315.217
• InChiKey: HZRNEYSDXGIQGY-GPMKSPRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  166
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-deoxy-2-propionylamido-α-D-glucopyranosyl phosphate 、 尿苷-5'-三磷酸 在 yeast inorganic pyrophosphatase 、 N-acetylglucosamine-1-phosphate pyrophosphorylase from C_. jejuni NCTC 11168 、 三羟甲基氨基甲烷盐酸盐 、 magnesium chloride 作用下， 反应 2.0h， 以79.9%的产率得到uridine-5'-(2-deoxy-2-propionylamido-α-D-glucopyranosyl diphosphate)
  参考文献：
  名称：

  A chemoenzymatic route to synthesize unnatural sugar nucleotides using a novel N-acetylglucosamine-1-phosphate pyrophosphorylase from Camphylobacter jejuni NCTC 11168

  摘要：

  A novel N-acetylglucosamine-1-phosphate pyrophosphorylase was identified from Campylobacter jejuni NCTC 11168. An unprecedented degree of substrate promiscuity has been revealed by systematic studies on its substrate specificities towards sugar-1-P and NTP. The yields of the synthetic reaction of seven kinds of sugar nucleotides catalyzed by the enzyme were up to 60%. In addition, the yields of the other nine were around 20%. With this enzyme, three novel sugar nucleotide analogs were synthesized on a preparative scale and well characterized. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.06.003
• 作为产物：
  描述：

  D-氨基葡萄糖-1-磷酸 、 1-(1-氧代丙氧基)-2,5-吡咯烷二酮 在 氢氧化钾 作用下， 以 四氢呋喃 、 水 为溶剂， 以79%的产率得到2-deoxy-2-propionylamido-α-D-glucopyranosyl phosphate
  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.
• A chemoenzymatic route to synthesize unnatural sugar nucleotides using a novel N-acetylglucosamine-1-phosphate pyrophosphorylase from Camphylobacter jejuni NCTC 11168
  作者：Junqiang Fang、Mengyang Xue、Guofeng Gu、Xian-wei Liu、Peng George Wang

  DOI：10.1016/j.bmcl.2013.06.003

  日期：2013.8

  A novel N-acetylglucosamine-1-phosphate pyrophosphorylase was identified from Campylobacter jejuni NCTC 11168. An unprecedented degree of substrate promiscuity has been revealed by systematic studies on its substrate specificities towards sugar-1-P and NTP. The yields of the synthetic reaction of seven kinds of sugar nucleotides catalyzed by the enzyme were up to 60%. In addition, the yields of the other nine were around 20%. With this enzyme, three novel sugar nucleotide analogs were synthesized on a preparative scale and well characterized. (C) 2013 Elsevier Ltd. All rights reserved.