(2R,3S)-hex-4-yne-2,3-diol | 1356477-69-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S)-hex-4-yne-2,3-diol
• CAS: 1356477-69-4
• 化学式: C₆H₁₀O₂
• 分子量: 114.144
• InChiKey: ZIWDSGVMDWLWET-RITPCOANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  环己酮二甲缩酮 、 (2R,3S)-hex-4-yne-2,3-diol 在 硫酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 (2R,3S)-2,3-(cyclohexylidenedioxy)-hex-4-yne
  参考文献：
  名称：

  Stereochemical diversity of AI-2 analogs modulates quorum sensing in Vibrio harveyi and Escherichia coli

  摘要：

  Bacteria coordinate population-dependent behaviors such as virulence by intra-and inter-species communication (quorum sensing). Autoinducer-2 (AI-2) regulates inter-species quorum sensing. AI-2 derives from the spontaneous cyclisation of linear (S)-4,5-dihydroxypentanedione (DPD) into two isomeric forms in dynamic equilibrium. Different species of bacteria have different classes of AI-2 receptors (LsrB and LuxP) which bind to different cyclic forms. In the present work, DPD analogs with a new stereocenter at C-5 (4,5-dihydroxyhexanediones (DHDs)) have been synthesized and their biological activity tested in two bacteria. (4S, 5R)-DHD is a synergistic agonist in Escherichia coli (which contains the LsrB receptor), while it is an agonist in Vibrio harveyi (LuxP), displaying the strongest agonistic activity reported so far (EC50 = 0.65 mu M) in this organism. Thus, modification at C-5 opens the way to novel methods to manipulate quorum sensing as a method for controlling bacteria. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.11.007
• 作为产物：
  描述：

  (2R)-2-t-butyldiphenylsilyloxyhex-4-yn-3-one 在 B-isopinocampheyl-9-borabicyclo[3.3.1]nonane 、 水 、 氯化铵 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 (2R,3S)-hex-4-yne-2,3-diol
  参考文献：
  名称：

  Stereochemical diversity of AI-2 analogs modulates quorum sensing in Vibrio harveyi and Escherichia coli

  摘要：

  Bacteria coordinate population-dependent behaviors such as virulence by intra-and inter-species communication (quorum sensing). Autoinducer-2 (AI-2) regulates inter-species quorum sensing. AI-2 derives from the spontaneous cyclisation of linear (S)-4,5-dihydroxypentanedione (DPD) into two isomeric forms in dynamic equilibrium. Different species of bacteria have different classes of AI-2 receptors (LsrB and LuxP) which bind to different cyclic forms. In the present work, DPD analogs with a new stereocenter at C-5 (4,5-dihydroxyhexanediones (DHDs)) have been synthesized and their biological activity tested in two bacteria. (4S, 5R)-DHD is a synergistic agonist in Escherichia coli (which contains the LsrB receptor), while it is an agonist in Vibrio harveyi (LuxP), displaying the strongest agonistic activity reported so far (EC50 = 0.65 mu M) in this organism. Thus, modification at C-5 opens the way to novel methods to manipulate quorum sensing as a method for controlling bacteria. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.11.007