galactose-α-1-phosphate barium salt | 103213-39-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: galactose-α-1-phosphate barium salt
• 英文别名: barium α-D-galactopyranosyl-1-phosphate；O¹-Phosphono-α-D-galactopyranose; Barium；Alpha-D-galactose-1-phosphate barium salt；barium(2+);[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate
• CAS: 103213-39-4
• 化学式: Ba*C₆H₁₁O₉P
• 分子量: 395.452
• InChiKey: FUUVVUUKTPWLJE-ZFWXJGAOSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  -4.75
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  162.57
• 氢给体数：
  4.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  uridine 5'-triphosphate trisodium salt 、 galactose-α-1-phosphate barium salt 在 sodium,[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl [hydroxy-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphosphoryl] phosphate 作用下， 以43%的产率得到UDP-Gal
  参考文献：
  名称：

  Practical enzyme-based syntheses of uridine 5'-diphosphogalactose and uridine 5'-diphospho-N-acetylgalactosamine on a gram scale

  摘要：

  Practical enzyme-based routes for the syntheses of uridine 5'-diphosphogalactose (UDP-Gal) and uridine 5'-diphospho-N-acetylgalactosamine (UDP-GalNAc) on millimole scales have been developed. The activity of galactokinase (EC 2.7.1.6) in crude enzyme extracts from galactose-adapted yeast, coupled to a regenerating system for ATP, provides convenient and economical access to galactose-alpha-1-phosphate (Gal-1-P) and galactosamine-alpha-1-phosphate (GalN-1-P). The transfer of UMP to the sugar-1-phosphates was also accomplished enzymatically by Gal-1-P uridyltransferase (EC 2.7.7.12) using uridine 5'-diphosphoglucose (UDP-Glc) as the UMP donor. UDP-Glc was in turn regenerated in situ from glucose-1-phosphate and UTP using UDP-Glc pyrophosphorylase (EC 2.7.7.9). The only chemical step in the sequence was the acetylation of UDP-GalN to afford UDP-GalNAc using N-acetoxysuccinimide. The moderate overall yields (43% and 34% for UDP-Gal and UDP-GalNAc from Gal-1-P and GalN-1-P, respectively) were compensated by the straightforward preparation of the starting materials, UTP and the corresponding sugar-1-P.

  DOI：

  10.1021/jo00027a029
• 作为产物：
  描述：

  D-吡喃葡萄糖 在 disodium acetyl phosphate 、 adenosine 5'-triphosphate disodium salt 、 barium(II) chloride 作用下， 以74%的产率得到galactose-α-1-phosphate barium salt
  参考文献：
  名称：

  Practical enzyme-based syntheses of uridine 5'-diphosphogalactose and uridine 5'-diphospho-N-acetylgalactosamine on a gram scale

  摘要：

  Practical enzyme-based routes for the syntheses of uridine 5'-diphosphogalactose (UDP-Gal) and uridine 5'-diphospho-N-acetylgalactosamine (UDP-GalNAc) on millimole scales have been developed. The activity of galactokinase (EC 2.7.1.6) in crude enzyme extracts from galactose-adapted yeast, coupled to a regenerating system for ATP, provides convenient and economical access to galactose-alpha-1-phosphate (Gal-1-P) and galactosamine-alpha-1-phosphate (GalN-1-P). The transfer of UMP to the sugar-1-phosphates was also accomplished enzymatically by Gal-1-P uridyltransferase (EC 2.7.7.12) using uridine 5'-diphosphoglucose (UDP-Glc) as the UMP donor. UDP-Glc was in turn regenerated in situ from glucose-1-phosphate and UTP using UDP-Glc pyrophosphorylase (EC 2.7.7.9). The only chemical step in the sequence was the acetylation of UDP-GalN to afford UDP-GalNAc using N-acetoxysuccinimide. The moderate overall yields (43% and 34% for UDP-Gal and UDP-GalNAc from Gal-1-P and GalN-1-P, respectively) were compensated by the straightforward preparation of the starting materials, UTP and the corresponding sugar-1-P.

  DOI：

  10.1021/jo00027a029

文献信息

• Protecting-Group-Free Synthesis of Glycosyl 1–Phosphates
  作者：Landon John G. Edgar、Somnath Dasgupta、Mark Nitz

  DOI：10.1021/ol3019083

  日期：2012.8.17

  Glycosyl 1-phosphates enriched in the alpha-anomer are obtained without the use of protecting groups in two steps starting from the free hemiacetal. Condensation of free hemiacetals with toluenesulfonylhydrazide yields a range of glycosylsulfonohydrazide donors which can be oxidized using cupric chloride in the presence of phosphoric acid and the coordinating additive 2-methyl-2-oxazoline to give useful yields of the fully deprotected glycosyl 1-phosphates.