L-rhamnulose 1-phosphate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: L-rhamnulose 1-phosphate
• 英文别名: [(3R,4R,5S)-2,3,4-trihydroxy-5-methyloxolan-2-yl]methyl dihydrogen phosphate
• 化学式: C₆H₁₃O₈P
• 分子量: 244.138
• InChiKey: JSTHOQJVFMNMOW-NSHGFSBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  137
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  L-rhamnulose 1-phosphate 在 水 作用下， 反应 15.0h， 以96%的产率得到L-rhamnulose
  参考文献：
  名称：

  6-deoxy-L-lyxo- and 6-deoxy-L-arabino-hexulose 1-phosphates. Enzymatic syntheses by antagonistic metabolic pathways

  摘要：

  Efficient large-scale syntheses of the title compounds (up to 0. 1 mole) from readily available precursors have been accomplished along destructive as well as constructive biosynthetic routes by employing overexpressed enzymes from E. coli. The first route, which consists of an aldose isomerization-ketose phosphorylation sequence, utilizes natural L-fucose and L-rhamnose as the respective sources of chirality. The key reaction of the second route, which starts from racemic 2-hydroxypropanal and achiral dihydroxyacetone phosphate, is a diastereospecific aldol addition with complete kinetic resolution.

  DOI：

  10.1016/s0957-4166(00)80227-x
• 作为产物：
  描述：

  L-rhamnopyranose 在 氢氧化钾 、 phosphoenolpyruvic acid monopotassium salt 、 5’-三磷酸腺苷 作用下， 反应 8.0h， 生成 L-rhamnulose 1-phosphate
  参考文献：
  名称：

  6-deoxy-L-lyxo- and 6-deoxy-L-arabino-hexulose 1-phosphates. Enzymatic syntheses by antagonistic metabolic pathways

  摘要：

  Efficient large-scale syntheses of the title compounds (up to 0. 1 mole) from readily available precursors have been accomplished along destructive as well as constructive biosynthetic routes by employing overexpressed enzymes from E. coli. The first route, which consists of an aldose isomerization-ketose phosphorylation sequence, utilizes natural L-fucose and L-rhamnose as the respective sources of chirality. The key reaction of the second route, which starts from racemic 2-hydroxypropanal and achiral dihydroxyacetone phosphate, is a diastereospecific aldol addition with complete kinetic resolution.

  DOI：

  10.1016/s0957-4166(00)80227-x

文献信息

• Enzymatic syntheses of rare ketose 1-phosphates
  作者：Wolf-Dieter Fessner、Josefa Badía、Oliver Eyrisch、Achim Schneider、Gudrun Sinerius

  DOI：10.1016/s0040-4039(00)79140-4

  日期：1992.9

  Ketose 1-phosphates are obtained from aldehydes and dihydroxyacetone phosphate by enzymatic aldol addition, and from aldoses (or ketoses) by isomerization/phosphorylation. The microbial enzymes employed are readily available by overexpression.
• Facile synthesis of 6-deoxy-l-arabino-hexulose (l-rhamnulose) 1-phosphate via regioselective phosphorylation of the unprotected sugar
  作者：P. Zhou、G. Lajoie、J.F. Honek、P.T.C. Nambiar、O.P. Ward

  DOI：10.1016/s0008-6215(00)91005-x

  日期：1992.7
• 6-deoxy-L-lyxo- and 6-deoxy-L-arabino-hexulose 1-phosphates. Enzymatic syntheses by antagonistic metabolic pathways
  作者：Wolf-Dieter Fessner、Achim Schneider、Oliver Eyrisch、Gudrun Sinerius、Josefa Badía

  DOI：10.1016/s0957-4166(00)80227-x

  日期：1993.6

  Efficient large-scale syntheses of the title compounds (up to 0. 1 mole) from readily available precursors have been accomplished along destructive as well as constructive biosynthetic routes by employing overexpressed enzymes from E. coli. The first route, which consists of an aldose isomerization-ketose phosphorylation sequence, utilizes natural L-fucose and L-rhamnose as the respective sources of chirality. The key reaction of the second route, which starts from racemic 2-hydroxypropanal and achiral dihydroxyacetone phosphate, is a diastereospecific aldol addition with complete kinetic resolution.