dibenzyl 3,4,6-tri-O-acetyl-2-deoxy-2-formamido-α-D-glucopyranose 1-phosphate | 1228149-33-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dibenzyl 3,4,6-tri-O-acetyl-2-deoxy-2-formamido-α-D-glucopyranose 1-phosphate
• CAS: 1228149-33-4
• 化学式: C₂₇H₃₂NO₁₂P
• 分子量: 593.524
• InChiKey: JBQVAUNJLYQVMU-RFNQJFSXSA-N

反应信息

• 作为反应物：
  描述：

  dibenzyl 3,4,6-tri-O-acetyl-2-deoxy-2-formamido-α-D-glucopyranose 1-phosphate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Phosphorylase-catalyzed N-formyl-α-glucosaminylation of maltooligosaccharides

  摘要：

  This paper describes the phosphorylase-catalyzed enzymatic N-formyl-alpha-glucosaminylation of maltooligosaccharides for direct incorporation of 2-deoxy-2-formamido-alpha-D-glucopyranose units into maltooligosaccharides. When the reaction of 2-deoxy-2-formamido-alpha-D-glucopyranose-1-phosphate (GlcNF-1-P) as the glycosyl donor and maltotetraose as a glycosyl acceptor was performed in the presence of phosphorylase, the N-formyl-alpha-D-glucosaminylated pentasaccharide was produced, as confirmed by MALDI-TOF MS. Furthermore, the glucoamylase-catalyzed reaction of the crude products supported that the 2-deoxy-2-formamido-alpha-D-glucopyranoside unit was positioned at the non-reducing end of the pentasaccharide. The pentasaccharide was isolated from the crude products and its structure was further determined by the (1)H NMR analysis. On the other hand, when the phosphorylase-catalyzed reactions of maltotriose and maltopentaose using GlcNF-1-P were conducted, no N-formyl-alpha-glucosaminylation took place in the former system, whereas the latter system gave N-formyl-alpha-D-glucosaminylated oligosaccharides with various degrees of polymerization. These results could be explained by the recognition behavior of phosphorylase toward maltooligosaccharides. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.01.001
• 作为产物：
  描述：

  在 双氧水 作用下， 以 二氯甲烷 、 水 为溶剂， 以0.14 g的产率得到dibenzyl 3,4,6-tri-O-acetyl-2-deoxy-2-formamido-α-D-glucopyranose 1-phosphate
  参考文献：
  名称：

  Phosphorylase-catalyzed N-formyl-α-glucosaminylation of maltooligosaccharides

  摘要：

  This paper describes the phosphorylase-catalyzed enzymatic N-formyl-alpha-glucosaminylation of maltooligosaccharides for direct incorporation of 2-deoxy-2-formamido-alpha-D-glucopyranose units into maltooligosaccharides. When the reaction of 2-deoxy-2-formamido-alpha-D-glucopyranose-1-phosphate (GlcNF-1-P) as the glycosyl donor and maltotetraose as a glycosyl acceptor was performed in the presence of phosphorylase, the N-formyl-alpha-D-glucosaminylated pentasaccharide was produced, as confirmed by MALDI-TOF MS. Furthermore, the glucoamylase-catalyzed reaction of the crude products supported that the 2-deoxy-2-formamido-alpha-D-glucopyranoside unit was positioned at the non-reducing end of the pentasaccharide. The pentasaccharide was isolated from the crude products and its structure was further determined by the (1)H NMR analysis. On the other hand, when the phosphorylase-catalyzed reactions of maltotriose and maltopentaose using GlcNF-1-P were conducted, no N-formyl-alpha-glucosaminylation took place in the former system, whereas the latter system gave N-formyl-alpha-D-glucosaminylated oligosaccharides with various degrees of polymerization. These results could be explained by the recognition behavior of phosphorylase toward maltooligosaccharides. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.01.001