1,2-O-isopropylidene-3-O-methyl-5-O-(p-toluenesulfonyl)-α-D-ribofuranose | 35506-62-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,2-O-isopropylidene-3-O-methyl-5-O-(p-toluenesulfonyl)-α-D-ribofuranose
• CAS: 35506-62-8
• 化学式: C₁₆H₂₂O₇S
• 分子量: 358.412
• InChiKey: LLDNGDWGHIJMCN-KBUPBQIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.59
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  80.29
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  DL-高半胱氨酸 、 1,2-O-isopropylidene-3-O-methyl-5-O-(p-toluenesulfonyl)-α-D-ribofuranose 在 sodium hydroxide 、 盐酸 作用下， 以 水 为溶剂， 反应 12.0h， 以30%的产率得到S-(5-deoxy-1,2-O-isopropylidene-3-O-methyl-α-D-ribofuranos-5-yl)homocysteine
  参考文献：
  名称：

  Inhibition of S-ribosylhomocysteinase (LuxS) by substrate analogues modified at the ribosyl C-3 position

  摘要：

  S-Ribosylhomocysteinase (LuxS) catalyzes the cleavage of the thioether bond of S-ribosylhomocysteine (SRH) to produce homocysteine and 4,5-dihydroxy-2,3-pentanedione (DPD), which is the precursor of type 2 autoinducer for bacterial cell-cell communication. In this work, we have synthesized several SRH analogues modi. ed at the ribose C3 position as potential inhibitors of LuxS. While removal or methylation of the C3-OH resulted in simple competitive inhibitors of moderate potency, inversion of the C3 stereochemistry or substitution of. uorine for C3-OH resulted in slow-binding inhibitors of improved potency. The most potent inhibitor showed a K*(I) value of 0.43 mu M. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.07.057
• 作为产物：
  描述：

  对甲苯磺酰氯 、 ((3aR,5R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[2,3-d] [1,3]dioxol-5-yl)methanol 在 吡啶 作用下， 反应 20.0h， 以72%的产率得到1,2-O-isopropylidene-3-O-methyl-5-O-(p-toluenesulfonyl)-α-D-ribofuranose
  参考文献：
  名称：

  Inhibition of S-ribosylhomocysteinase (LuxS) by substrate analogues modified at the ribosyl C-3 position

  摘要：

  S-Ribosylhomocysteinase (LuxS) catalyzes the cleavage of the thioether bond of S-ribosylhomocysteine (SRH) to produce homocysteine and 4,5-dihydroxy-2,3-pentanedione (DPD), which is the precursor of type 2 autoinducer for bacterial cell-cell communication. In this work, we have synthesized several SRH analogues modi. ed at the ribose C3 position as potential inhibitors of LuxS. While removal or methylation of the C3-OH resulted in simple competitive inhibitors of moderate potency, inversion of the C3 stereochemistry or substitution of. uorine for C3-OH resulted in slow-binding inhibitors of improved potency. The most potent inhibitor showed a K*(I) value of 0.43 mu M. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.07.057