5'-tryptophanamido-5'-deoxy-2',3'-O-isopropylideneuridine | 1269140-88-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5'-tryptophanamido-5'-deoxy-2',3'-O-isopropylideneuridine
• CAS: 1269140-88-6
• 化学式: C₂₃H₂₇N₅O₆
• 分子量: 469.497
• InChiKey: CWEIUSQHJUOEPA-HQUDQQMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.12
• 重原子数：
  34.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  153.46
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  5'-tryptophanamido-5'-deoxy-2',3'-O-isopropylideneuridine 、 (2,3,4,5,6-pentafluorophenyl) 2-[(2R,3S,4R,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]acetate 在 4-二甲氨基吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以78%的产率得到
  参考文献：
  名称：

  Synthesis of sugar–amino acid–nucleosides as potential glycosyltransferase inhibitors

  摘要：

  Sugar-amino acid-nucleosides (SAAN) were synthesized to mimic glycosyl nucleotide donors based on the hypothesis that a basic amino acid may interact with carboxylate groups of the enzyme in a manner similar to the diphosphate metal ion complex. C-Glycoside analogues of the D-galactopyranose or L-arabinofuranose ring systems, and four amino acids (lysine, glutamine, tryptophan, and histidine), were chosen for this study. The targets were synthesized and tested against GlfT2, a galactofuranosyltransferase essential for cell wall galactan biosynthesis in Mycobacterium tuberculosis. The inhibition assay showed that analogues containing histidine and tryptophan are moderate inhibitors of GlfT2. Crown Copyright (C) 2010 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.11.044
• 作为产物：
  描述：

  在 哌啶 作用下， 反应 0.17h， 生成 5'-tryptophanamido-5'-deoxy-2',3'-O-isopropylideneuridine
  参考文献：
  名称：

  Synthesis of sugar–amino acid–nucleosides as potential glycosyltransferase inhibitors

  摘要：

  Sugar-amino acid-nucleosides (SAAN) were synthesized to mimic glycosyl nucleotide donors based on the hypothesis that a basic amino acid may interact with carboxylate groups of the enzyme in a manner similar to the diphosphate metal ion complex. C-Glycoside analogues of the D-galactopyranose or L-arabinofuranose ring systems, and four amino acids (lysine, glutamine, tryptophan, and histidine), were chosen for this study. The targets were synthesized and tested against GlfT2, a galactofuranosyltransferase essential for cell wall galactan biosynthesis in Mycobacterium tuberculosis. The inhibition assay showed that analogues containing histidine and tryptophan are moderate inhibitors of GlfT2. Crown Copyright (C) 2010 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.11.044