2,3,5-tri-O-benzyl-L-arabinofuranosylacetic acid | 1269140-67-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,5-tri-O-benzyl-L-arabinofuranosylacetic acid
• CAS: 1269140-67-1
• 化学式: C₂₈H₃₀O₆
• 分子量: 462.543
• InChiKey: TWONDOXRGFPSAX-ILXHYJSTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.62
• 重原子数：
  34.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  74.22
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  五氟苯酚 、 2,3,5-tri-O-benzyl-L-arabinofuranosylacetic acid 在 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 生成 perfluorophenyl 2-((3S,4S,5S)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)acetate
  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：

  2-((3S,4S,5S)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)acetaldehyde 在 sodium perchlorate 、 双氧水 、 sodium phosphate 作用下， 以 水 、 乙腈 为溶剂， 以78%的产率得到2,3,5-tri-O-benzyl-L-arabinofuranosylacetic acid
  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