2-azi-2-deoxy-D-arabino-hexitol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-azi-2-deoxy-D-arabino-hexitol
• 英文别名: (1R,2S,3R)-1-[3-(hydroxymethyl)diazirin-3-yl]butane-1,2,3,4-tetrol
• 化学式: C₆H₁₂N₂O₅
• 分子量: 192.172
• InChiKey: BLEAPPKMLFNUNV-WDCZJNDASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.1
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  126
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-azi-2-deoxy-D-arabino-hexitol 在 水 作用下， 反应 1.0h， 以77%的产率得到2-Deoxy-D-glucose
  参考文献：
  名称：

  Photolysis of 2-azi-2-deoxy-d-arabino-hexitol and analogous hexitols; the ineffectiveness of certain carbohydrate diazirines as photoaffinity labels

  摘要：

  Three diazirines 2-azi-2-deoxy-D-arabino-hexitol (4), its 1-deoxy analogue (5), and 3-azi-3,6-dideoxy-L-xylo-hexitol (9) were synthesised and their products of photolysis analysed by TLC. Diazirine 4 gave exclusively 2-deoxy-D-arabino-hexose (12), 5 gave predominantly 1,2-dideoxy-D-erythro-3-hexulose (10) and 1-deoxy-D-glucitol (11), and 9 did not yield any main product. Carrying out the irradiation of 4 in D2O gave selectively (2S)-2-deoxy-D-arabino-(2-H-2)hexose (12a). The results indicate that photolysis of a diazirine flanked by a hydroxymethyl group, as in compound 4, leads to a rapid and stereoselective intramolecular reaction of the intermediate. This may be an explanation of why compound 4 is ineffective as a photoaffinity reagent for mannitol permease (D-mannitol-specific enzyme II) of the E. coli phosphotransferase system for which it is a substrate. A secondary hydroxymethylene group has a less pronounced effect and still allows some reaction with the medium.

  DOI：

  10.1016/0008-6215(93)84209-o
• 作为产物：
  描述：

  D-fructose diethyl dithioacetal 在 氨 、 碘 、 对甲苯磺酸 、 溶剂黄146 、 三乙胺 、 mercury dichloride 、 mercury(II) oxide 、 hydroxylamine-O-sulfonic acid 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 16.5h， 生成 2-azi-2-deoxy-D-arabino-hexitol
  参考文献：
  名称：

  Photolysis of 2-azi-2-deoxy-d-arabino-hexitol and analogous hexitols; the ineffectiveness of certain carbohydrate diazirines as photoaffinity labels

  摘要：

  Three diazirines 2-azi-2-deoxy-D-arabino-hexitol (4), its 1-deoxy analogue (5), and 3-azi-3,6-dideoxy-L-xylo-hexitol (9) were synthesised and their products of photolysis analysed by TLC. Diazirine 4 gave exclusively 2-deoxy-D-arabino-hexose (12), 5 gave predominantly 1,2-dideoxy-D-erythro-3-hexulose (10) and 1-deoxy-D-glucitol (11), and 9 did not yield any main product. Carrying out the irradiation of 4 in D2O gave selectively (2S)-2-deoxy-D-arabino-(2-H-2)hexose (12a). The results indicate that photolysis of a diazirine flanked by a hydroxymethyl group, as in compound 4, leads to a rapid and stereoselective intramolecular reaction of the intermediate. This may be an explanation of why compound 4 is ineffective as a photoaffinity reagent for mannitol permease (D-mannitol-specific enzyme II) of the E. coli phosphotransferase system for which it is a substrate. A secondary hydroxymethylene group has a less pronounced effect and still allows some reaction with the medium.

  DOI：

  10.1016/0008-6215(93)84209-o

文献信息

• Photolysis of 2-azi-2-deoxy-d-arabino-hexitol and analogous hexitols; the ineffectiveness of certain carbohydrate diazirines as photoaffinity labels
  作者：Jochen Lehmann、Stefan Petry

  DOI：10.1016/0008-6215(93)84209-o

  日期：1993.2

  Three diazirines 2-azi-2-deoxy-D-arabino-hexitol (4), its 1-deoxy analogue (5), and 3-azi-3,6-dideoxy-L-xylo-hexitol (9) were synthesised and their products of photolysis analysed by TLC. Diazirine 4 gave exclusively 2-deoxy-D-arabino-hexose (12), 5 gave predominantly 1,2-dideoxy-D-erythro-3-hexulose (10) and 1-deoxy-D-glucitol (11), and 9 did not yield any main product. Carrying out the irradiation of 4 in D2O gave selectively (2S)-2-deoxy-D-arabino-(2-H-2)hexose (12a). The results indicate that photolysis of a diazirine flanked by a hydroxymethyl group, as in compound 4, leads to a rapid and stereoselective intramolecular reaction of the intermediate. This may be an explanation of why compound 4 is ineffective as a photoaffinity reagent for mannitol permease (D-mannitol-specific enzyme II) of the E. coli phosphotransferase system for which it is a substrate. A secondary hydroxymethylene group has a less pronounced effect and still allows some reaction with the medium.