2-O-β-D-glucopyranosyl-D-xylose | 91463-79-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-O-β-D-glucopyranosyl-D-xylose
• 英文别名: 2-O-β-D-Glucopyranosyl-D-xylose；Glc(b1-2)aldehydo-Xyl；(2R,3S,4R)-3,4,5-trihydroxy-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypentanal
• CAS: 91463-79-5
• 化学式: C₁₁H₂₀O₁₀
• 分子量: 312.274
• InChiKey: AXHPKHDTOXXPGU-NPQLUEORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.4
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  177
• 氢给体数：
  7
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  laminaribiose 在 2-吗啉乙磺酸 、 ACL₀₇₂₉ 、 hydrogenphosphate 、 sodium hydroxide 、 4-羟乙基哌嗪乙磺酸 作用下， 以 水 为溶剂， 反应 70.0h， 生成 2-O-β-D-glucopyranosyl-D-xylose 、 3-O-β-D-glucopyranosyl-D-xylose
  参考文献：
  名称：

  Characterization of a laminaribiose phosphorylase from Acholeplasma laidlawii PG-8A and production of 1,3-β-d-glucosyl disaccharides

  摘要：

  We identified a glycoside hydrolase family 94 homolog (ACL0729) from Acholeplasma laidlawii PG-8A as a laminaribiose (1,3-beta-D-glucobiose) phosphorylase (EC 2.4.1.31). The recombinant ACL0729 produced in Escherichia coli catalyzed phosphorolysis of laminaribiose with inversion of the anomeric configuration in a typical sequential bi bi mechanism releasing alpha-D-glucose 1-phosphate and D-glucose. Laminaritriose (1,3-beta-D-glucotriose) was not an efficient substrate for ACL0729. The phosphorolysis is reversible, enabling synthesis of 1,3-beta-D-glucosyl disaccharides by reverse phosphorolysis with strict regioselectivity from alpha-D-glucose 1-phosphate as the donor and suitable monosaccharide acceptors (D-glucose, 2-deoxy-D-arabino-hexopyranose, D-xylose, D-glucuronic acid, 1,5-anhydro-D-glucitol, and D-mannose) with C-3 and C-4 equatorial hydroxyl groups. The D-glucose and 2-deoxy-D-arabino-hexopyranose caused significantly strong competitive substrate inhibition compared with other glucobiose phosphorylases reported, in which the acceptor competitively inhibited the binding of the donor substrate. By contrast, none of the examined disaccharides served as acceptor in the synthetic reaction. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.08.006

文献信息

• Characterization of a laminaribiose phosphorylase from Acholeplasma laidlawii PG-8A and production of 1,3-β-d-glucosyl disaccharides
  作者：Takanori Nihira、Yuka Saito、Motomitsu Kitaoka、Mamoru Nishimoto、Ken’ichi Otsubo、Hiroyuki Nakai

  DOI：10.1016/j.carres.2012.08.006

  日期：2012.11

  We identified a glycoside hydrolase family 94 homolog (ACL0729) from Acholeplasma laidlawii PG-8A as a laminaribiose (1,3-beta-D-glucobiose) phosphorylase (EC 2.4.1.31). The recombinant ACL0729 produced in Escherichia coli catalyzed phosphorolysis of laminaribiose with inversion of the anomeric configuration in a typical sequential bi bi mechanism releasing alpha-D-glucose 1-phosphate and D-glucose. Laminaritriose (1,3-beta-D-glucotriose) was not an efficient substrate for ACL0729. The phosphorolysis is reversible, enabling synthesis of 1,3-beta-D-glucosyl disaccharides by reverse phosphorolysis with strict regioselectivity from alpha-D-glucose 1-phosphate as the donor and suitable monosaccharide acceptors (D-glucose, 2-deoxy-D-arabino-hexopyranose, D-xylose, D-glucuronic acid, 1,5-anhydro-D-glucitol, and D-mannose) with C-3 and C-4 equatorial hydroxyl groups. The D-glucose and 2-deoxy-D-arabino-hexopyranose caused significantly strong competitive substrate inhibition compared with other glucobiose phosphorylases reported, in which the acceptor competitively inhibited the binding of the donor substrate. By contrast, none of the examined disaccharides served as acceptor in the synthetic reaction. (C) 2012 Elsevier Ltd. All rights reserved.