GlcA(a1-4)Glc(a1-4)Glc(a1-4)Glc

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: GlcA(a1-4)Glc(a1-4)Glc(a1-4)Glc
• 英文别名: (2S,3S,4S,5R,6S)-6-[(2R,3S,4R,5R,6R)-6-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
• 化学式: C₂₄H₄₀O₂₂
• 分子量: 680.568
• InChiKey: MTRXWFBXGBSGQU-CAZQFPEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -8.8
• 重原子数：
  46
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  365
• 氢给体数：
  14
• 氢受体数：
  22

反应信息

• 作为产物：
  描述：

  maltotriose 、 Alpha-D-葡糖醛酸-1-磷酸 在 Aquifex aeolicus VF₅ 作用下， 反应 48.0h， 生成 GlcA(a1-4)Glc(a1-4)Glc(a1-4)Glc
  参考文献：
  名称：

  Enzymatic α-glucuronylation of maltooligosaccharides using α-glucuronic acid 1-phosphate as glycosyl donor catalyzed by a thermostable phosphorylase from Aquifex aeolicus VF5

  摘要：

  This paper describes thermostable phosphorylase-catalyzed alpha-glucuronylation of maltooligosaccharides for the direct synthesis of anionic oligosaccharides having a glucuronic acid residue at the non-reducing end. When the reaction of a-glucuronic acid 1-phosphate (GlcA-1-P) as a glycosyl donor and maltotriose as a glycosyl acceptor was performed in the presence of thermostable phosphorylase from Aquifex aeolicus VF5, high performance anion exchange chromatography analysis of the reaction mixture suggested the production of a glucuronylated tetrasaccharide, whose structure was also confirmed by the MALDI-TOF MS measurement of the crude products. Furthermore, treatment of the crude products with glucoamylase supported that the alpha-glucuronic acid unit was positioned at the non-reducing end of the tetrasaccharide and H-1 NMR analysis suggested that it was bound in an alpha-(1 -> 4)-linkage. When the alpha-glucuronylation of maltotetraose using GlcA-1-P was conducted, alpha-glucuronylated oligosaccharides with various degrees of polymerization were produced. On the other hand, the alpha-glucuronylation of maltotetraose using GlcA-1-P in the presence of potato phosphorylase did not occur at all, indicating no recognition of GlcA-1-P by potato phosphorylase. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.12.022

文献信息

• Enzymatic α-glucuronylation of maltooligosaccharides using α-glucuronic acid 1-phosphate as glycosyl donor catalyzed by a thermostable phosphorylase from Aquifex aeolicus VF5
  作者：Yuta Umegatani、Hironori Izawa、Mutsuki Nawaji、Kazuya Yamamoto、Akiko Kubo、Michiyo Yanase、Takeshi Takaha、Jun-ichi Kadokawa

  DOI：10.1016/j.carres.2011.12.022

  日期：2012.3

  This paper describes thermostable phosphorylase-catalyzed alpha-glucuronylation of maltooligosaccharides for the direct synthesis of anionic oligosaccharides having a glucuronic acid residue at the non-reducing end. When the reaction of a-glucuronic acid 1-phosphate (GlcA-1-P) as a glycosyl donor and maltotriose as a glycosyl acceptor was performed in the presence of thermostable phosphorylase from Aquifex aeolicus VF5, high performance anion exchange chromatography analysis of the reaction mixture suggested the production of a glucuronylated tetrasaccharide, whose structure was also confirmed by the MALDI-TOF MS measurement of the crude products. Furthermore, treatment of the crude products with glucoamylase supported that the alpha-glucuronic acid unit was positioned at the non-reducing end of the tetrasaccharide and H-1 NMR analysis suggested that it was bound in an alpha-(1 -> 4)-linkage. When the alpha-glucuronylation of maltotetraose using GlcA-1-P was conducted, alpha-glucuronylated oligosaccharides with various degrees of polymerization were produced. On the other hand, the alpha-glucuronylation of maltotetraose using GlcA-1-P in the presence of potato phosphorylase did not occur at all, indicating no recognition of GlcA-1-P by potato phosphorylase. (C) 2011 Elsevier Ltd. All rights reserved.