GalN-HCl-β-DMT | 1415305-18-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: GalN-HCl-β-DMT
• 英文别名: 4,6-dimethoxy-1,3,5-triazin-2-yl β-D-galactosamine hydrochloride；GalN-β-DMT
• CAS: 1415305-18-8
• 化学式: C₁₁H₁₈N₄O₇*ClH
• 分子量: 354.747
• InChiKey: PGBUESZWQUCCDM-BCSHSFFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.54
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  162.3
• 氢给体数：
  4.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  GalN-HCl-β-DMT 在 exo-β-D-glucosaminidase from Amycolatopsis orientalis 作用下， 以 aq. acetate buffer 为溶剂， 反应 3.5h， 生成 Galactosamine 、 4,6-二甲氧基-1,3,5-三嗪-2(1H)-酮
  参考文献：
  名称：

  4,6-Dimethoxy-1,3,5-triazin-2-yl β-d-glycosaminides: Novel Substrates for Transglycosylation Reaction Catalyzed by Exo-β-d-glucosaminidase fromAmycolatopsis orientalis

  摘要：

  A novel sugar adduct, 4,6-dimethoxy-1,3,5-triazin-2-yl beta-D-glucosaminide (GlcN-beta-DMT), has been prepared by the reaction of D-glucosamine (GlcN) and 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-morpholinium chloride (DMT-MM). The adduct was recognized by exo-beta-D-glucosaminidase (GlcNase) from Amycolatopsis orientalis and transferred the GlcN moiety, giving rise to the corresponding glucosaminides. This chemo-enzymatic process was successfully applied to D-galactosamine (GalN). GalN-beta-DMT prepared directly from GalN and DMT-MM behaved as an efficient glycosyl donor for transfer of the GalN moiety catalyzed by the same enzyme. The introduction of the 4,6-dimethoxy-1,3,5-triazin-2-yl leaving group to the anomeric center significantly enhanced transglycosylating ability, resulting in the efficient glycosidase-catalyzed synthesis of glycosaminides.

  DOI：

  10.1080/07328303.2012.698437
• 作为产物：
  描述：

  D-(+)-galactosamine hydrochloride 、 4-(4,6-二甲氧基三嗪-2-基)-4-甲基吗啉盐酸盐 在 ammonium hydroxide 作用下， 以 水 为溶剂， 反应 6.0h， 以45%的产率得到GalN-HCl-β-DMT
  参考文献：
  名称：

  4,6-Dimethoxy-1,3,5-triazin-2-yl β-d-glycosaminides: Novel Substrates for Transglycosylation Reaction Catalyzed by Exo-β-d-glucosaminidase fromAmycolatopsis orientalis

  摘要：

  A novel sugar adduct, 4,6-dimethoxy-1,3,5-triazin-2-yl beta-D-glucosaminide (GlcN-beta-DMT), has been prepared by the reaction of D-glucosamine (GlcN) and 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-morpholinium chloride (DMT-MM). The adduct was recognized by exo-beta-D-glucosaminidase (GlcNase) from Amycolatopsis orientalis and transferred the GlcN moiety, giving rise to the corresponding glucosaminides. This chemo-enzymatic process was successfully applied to D-galactosamine (GalN). GalN-beta-DMT prepared directly from GalN and DMT-MM behaved as an efficient glycosyl donor for transfer of the GalN moiety catalyzed by the same enzyme. The introduction of the 4,6-dimethoxy-1,3,5-triazin-2-yl leaving group to the anomeric center significantly enhanced transglycosylating ability, resulting in the efficient glycosidase-catalyzed synthesis of glycosaminides.

  DOI：

  10.1080/07328303.2012.698437