1-amino-1,4-anhydro-1,N-didehydro-2,3-O-isopropylidene-5-O-methanesulfonyl-1-methyl-D-ribitol | 1338787-41-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-amino-1,4-anhydro-1,N-didehydro-2,3-O-isopropylidene-5-O-methanesulfonyl-1-methyl-D-ribitol
• CAS: 1338787-41-9
• 化学式: C₁₀H₁₇NO₅S
• 分子量: 263.315
• InChiKey: ZIZVDMDELKXJEA-HRDYMLBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.33
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  74.19
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-amino-1,4-anhydro-1,N-didehydro-2,3-O-isopropylidene-5-O-methanesulfonyl-1-methyl-D-ribitol 在 水 、 三氟乙酸 、 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 39.25h， 生成 S-(1-amino-1,4-anhydro-5-deoxy-1,N-didehydro-1-methyl-D-ribitol-5-yl)-L-homocysteine
  参考文献：
  名称：

  Inhibition of LuxS by S-ribosylhomocysteine analogues containing a [4-aza]ribose ring

  摘要：

  LuxS (S-ribosylhomocysteinase) catalyzes the cleavage of the thioether linkage of S-ribosylhomocysteine (SRH) to produce homocysteine and 4,5-dihydroxy-2,3-pentanedione (DPD), the precursor to a small signaling molecule that mediates interspecies bacterial communication called autoinducer 2 (AI-2). Inhibitors of LuxS should interfere with bacterial interspecies communication and potentially provide a novel class of antibacterial agents. In this work, SRH analogues containing substitution of a nitrogen atom for the endocyclic oxygen as well as various deoxyriboses were synthesized and evaluated for LuxS inhibition. Two of the [4-aza] SRH analogues showed modest competitive inhibition (K-I similar to 40 mu M), while most of the others were inactive. One compound that contains a hemiaminal moiety exhibited time-dependent inhibition, consistent with enzyme-catalyzed ring opening and conversion into a more potent species (K-I* = 3.5 mu M). The structure-activity relationship of the designed inhibitors highlights the importance of both the homocysteine and ribose moieties for high-affinity binding to LuxS active site. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.07.043
• 作为产物：
  描述：

  (2S,3R,4R)-1-methyl-2,3-isopropylidenedioxy-4-hydroxymethyl-1-pyrroline 、 甲基磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以85%的产率得到1-amino-1,4-anhydro-1,N-didehydro-2,3-O-isopropylidene-5-O-methanesulfonyl-1-methyl-D-ribitol
  参考文献：
  名称：

  Inhibition of LuxS by S-ribosylhomocysteine analogues containing a [4-aza]ribose ring

  摘要：

  LuxS (S-ribosylhomocysteinase) catalyzes the cleavage of the thioether linkage of S-ribosylhomocysteine (SRH) to produce homocysteine and 4,5-dihydroxy-2,3-pentanedione (DPD), the precursor to a small signaling molecule that mediates interspecies bacterial communication called autoinducer 2 (AI-2). Inhibitors of LuxS should interfere with bacterial interspecies communication and potentially provide a novel class of antibacterial agents. In this work, SRH analogues containing substitution of a nitrogen atom for the endocyclic oxygen as well as various deoxyriboses were synthesized and evaluated for LuxS inhibition. Two of the [4-aza] SRH analogues showed modest competitive inhibition (K-I similar to 40 mu M), while most of the others were inactive. One compound that contains a hemiaminal moiety exhibited time-dependent inhibition, consistent with enzyme-catalyzed ring opening and conversion into a more potent species (K-I* = 3.5 mu M). The structure-activity relationship of the designed inhibitors highlights the importance of both the homocysteine and ribose moieties for high-affinity binding to LuxS active site. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.07.043