5-C-methyl-L-psicose | 1072905-78-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-C-methyl-L-psicose
• 英文别名: (3S,4R,5S)-1,3,4,5,6-pentahydroxy-5-methylhexan-2-one
• CAS: 1072905-78-2
• 化学式: C₇H₁₄O₆
• 分子量: 194.185
• InChiKey: NCLYFSQEBHTEAF-QYNIQEEDSA-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：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  118
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-C-methyl-L-psicose 在 Tris-HCl buffer 、 manganese(ll) chloride 作用下， 以 水 为溶剂， 反应 7.0h， 以20%的产率得到5-C-methyl-L-fructose
  参考文献：
  名称：

  Green syntheses of new 2-C-methyl aldohexoses and 5-C-methyl ketohexoses: d-tagatose-3-epimerase (DTE)—a promiscuous enzyme

  摘要：

  The Kiliani synthesis oil the 4 readily accessible ketohexoses (D-fructose, D-tagatose, L-sorbose, D-psicose) allows access to 4 diastereomeric 2-C-methyl-aldohexoses (2-C-methyl-D-mannose, 2-C-methyl-D-talose, 2-C-methyl-L-gulose, 2-C-methyl-D-allose) and 4 diastereomeric 2-C-methyl-alditols (2-C-methyl-mannitol, 2-C-methyl-D-talitol, 2-C-methyl-L-gulitol, 2-C-methyl-D-allitol). Microbial oxidation of 2-C-methyl-D-mannitol and 2-C-metllyl-L-gulitol gave 5-C-methyl-D-fructose; Microbial oxidation of 2-C-methyl-D-talitol afforded 5-C-methyl-D-psicose, whereas 2-C-methyl-D-allitol formed 5-C-methyl-Lpsicose. Both enantiomers of 5-C-methyl-fructose were equilibrated by D-tagatose-3-epimerase (DTE) with both enantiomers of 5-C-methyl-psicose. These transformations demonstrate that polyol dehydrogenases and DTE act on branched synthetic sugars. Full NMR analyses show that 5-C-methyl-D-fructose is present as the P-pyranose and P-furanose forms in a ratio of 90:10; all pyranose and furanose forms of 5-C-methyl-D-psicose are present in solution. The combination of chemical and biological procedures allows the environmentally friendly generation of a new family of branched monosaccharides. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.07.034
• 作为产物：
  描述：

  2-C-methyl-D-allitol 在 Gluconobacter thailandicus NBRC 3254 cells 、 Tri-HCl buffer 作用下， 以 水 为溶剂， 反应 10.0h， 以70%的产率得到5-C-methyl-L-psicose
  参考文献：
  名称：

  Green syntheses of new 2-C-methyl aldohexoses and 5-C-methyl ketohexoses: d-tagatose-3-epimerase (DTE)—a promiscuous enzyme

  摘要：

  The Kiliani synthesis oil the 4 readily accessible ketohexoses (D-fructose, D-tagatose, L-sorbose, D-psicose) allows access to 4 diastereomeric 2-C-methyl-aldohexoses (2-C-methyl-D-mannose, 2-C-methyl-D-talose, 2-C-methyl-L-gulose, 2-C-methyl-D-allose) and 4 diastereomeric 2-C-methyl-alditols (2-C-methyl-mannitol, 2-C-methyl-D-talitol, 2-C-methyl-L-gulitol, 2-C-methyl-D-allitol). Microbial oxidation of 2-C-methyl-D-mannitol and 2-C-metllyl-L-gulitol gave 5-C-methyl-D-fructose; Microbial oxidation of 2-C-methyl-D-talitol afforded 5-C-methyl-D-psicose, whereas 2-C-methyl-D-allitol formed 5-C-methyl-Lpsicose. Both enantiomers of 5-C-methyl-fructose were equilibrated by D-tagatose-3-epimerase (DTE) with both enantiomers of 5-C-methyl-psicose. These transformations demonstrate that polyol dehydrogenases and DTE act on branched synthetic sugars. Full NMR analyses show that 5-C-methyl-D-fructose is present as the P-pyranose and P-furanose forms in a ratio of 90:10; all pyranose and furanose forms of 5-C-methyl-D-psicose are present in solution. The combination of chemical and biological procedures allows the environmentally friendly generation of a new family of branched monosaccharides. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.07.034