N-(tert-butoxycarbonyl)-S-(3,5-dideoxy-3-fluoro-1,2-O-isopropylidene-α-D-xylofuranos-5-yl)-L-homocysteine tert-butyl ester | 1193310-28-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(tert-butoxycarbonyl)-S-(3,5-dideoxy-3-fluoro-1,2-O-isopropylidene-α-D-xylofuranos-5-yl)-L-homocysteine tert-butyl ester
• CAS: 1193310-28-9
• 化学式: C₂₁H₃₆FNO₇S
• 分子量: 465.584
• InChiKey: QKBVBQTZORGKAJ-LVNYTYFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.56
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  92.32
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  N-(tert-butoxycarbonyl)-S-(3,5-dideoxy-3-fluoro-1,2-O-isopropylidene-α-D-xylofuranos-5-yl)-L-homocysteine tert-butyl ester 在 三氟乙酸 、 水 作用下， 反应 6.0h， 生成 S-(3,5-dideoxy-3-fluoro-α-D-xylofuranos-5-yl)-L-homocysteine 、 S-(3-deoxy-3-fluoro-β-D-xylosyl)-L-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：

  3-deoxy-3-fluoro-1,2-O-isopropylidene-5-O-methanesulfonyl-α-D-xylofuranose 、 (S)-叔丁基 2-(叔丁氧基羰基氨基)-4-疏基丁酸酯 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正庚烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.25h， 以92%的产率得到N-(tert-butoxycarbonyl)-S-(3,5-dideoxy-3-fluoro-1,2-O-isopropylidene-α-D-xylofuranos-5-yl)-L-homocysteine tert-butyl ester
  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