(2R,3S,4S,5S)-4-azido-2-[(2R,3S,4S,5S)-4-hydroxy-2-(hydroxymethyl)-5-octoxy-tetrahydrofuran-3-yl]oxy-5-(hydroxymethyl)tetrahydrofuran-3-ol | 848437-07-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2R,3S,4S,5S)-4-azido-2-[(2R,3S,4S,5S)-4-hydroxy-2-(hydroxymethyl)-5-octoxy-tetrahydrofuran-3-yl]oxy-5-(hydroxymethyl)tetrahydrofuran-3-ol
• 英文别名: (2R,3S,4S,5S)-4-azido-2-[(2R,3S,4S,5S)-4-hydroxy-2-(hydroxymethyl)-5-octoxyoxolan-3-yl]oxy-5-(hydroxymethyl)oxolan-3-ol
• CAS: 848437-07-0
• 化学式: C₁₈H₃₃N₃O₈
• 分子量: 419.475
• InChiKey: OBJMYGRBNWCMFH-FAZHARAESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  29
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  132
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S,5S)-4-azido-2-[(2R,3S,4S,5S)-4-hydroxy-2-(hydroxymethyl)-5-octoxy-tetrahydrofuran-3-yl]oxy-5-(hydroxymethyl)tetrahydrofuran-3-ol 在 水 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以73%的产率得到(2R,3S,4S,5S)-4-amino-2-[(2R,3S,4S,5S)-4-hydroxy-2-(hydroxymethyl)-5-octoxy-tetrahydrofuran-3-yl]oxy-5-(hydroxymethyl)tetrahydrofuran-3-ol
  参考文献：
  名称：

  Oligosaccharides as inhibitors of mycobacterial arabinosyltransferases. Di- and trisaccharides containing C-3 modified arabinofuranosyl residues

  摘要：

  The assembly of the arabinan portions of cell wall polysaccharicles in mycobacteria involves a family of arabinosyltransferases (AraT's) that promote the polymerization of decaprenolphosphoarabinose. Mycobacterial viability depends upon the ability of the organism to synthesize an intact arabinan and thus compounds that inhibit these AraT's are both useful biochemical tools as well as potential lead compounds for new anti-tuberculosis agents. We describe here the preparation of oligosaccharide fragments of mycobacterial arabinan that contain arabinofuranosyl residues modified at C-3 by the replacement of the hydroxyl group with an amino, azido or methoxy functionality. Subsequent testing of these oligosaccharides as inhibitors of mycobacterial AraT's revealed that all inhibited the enzymes, but to varying degrees. In further studies, each compound was shown to have only low activity as an inhibitor of mycobacterial growth. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.11.003
• 作为产物：
  描述：

  octyl 2,5-di-O-benzoyl-α-D-arabinofuranoside 在 N-碘代丁二酰亚胺 、 sodium methylate 、 silver trifluoromethanesulfonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.08h， 生成 (2R,3S,4S,5S)-4-azido-2-[(2R,3S,4S,5S)-4-hydroxy-2-(hydroxymethyl)-5-octoxy-tetrahydrofuran-3-yl]oxy-5-(hydroxymethyl)tetrahydrofuran-3-ol
  参考文献：
  名称：

  Oligosaccharides as inhibitors of mycobacterial arabinosyltransferases. Di- and trisaccharides containing C-3 modified arabinofuranosyl residues

  摘要：

  The assembly of the arabinan portions of cell wall polysaccharicles in mycobacteria involves a family of arabinosyltransferases (AraT's) that promote the polymerization of decaprenolphosphoarabinose. Mycobacterial viability depends upon the ability of the organism to synthesize an intact arabinan and thus compounds that inhibit these AraT's are both useful biochemical tools as well as potential lead compounds for new anti-tuberculosis agents. We describe here the preparation of oligosaccharide fragments of mycobacterial arabinan that contain arabinofuranosyl residues modified at C-3 by the replacement of the hydroxyl group with an amino, azido or methoxy functionality. Subsequent testing of these oligosaccharides as inhibitors of mycobacterial AraT's revealed that all inhibited the enzymes, but to varying degrees. In further studies, each compound was shown to have only low activity as an inhibitor of mycobacterial growth. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.11.003