1,4-α-D-glucopyranosyl-[1,2-β-D-glucopyranosyl]-D-glucose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,4-α-D-glucopyranosyl-[1,2-β-D-glucopyranosyl]-D-glucose
• 英文别名: Glc(b1-2)[Glc(a1-4)]b-Glc；(2R,3R,4S,5S,6R)-2-[(2R,3S,4S,5R,6R)-4,6-dihydroxy-2-(hydroxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• 化学式: C₁₈H₃₂O₁₆
• 分子量: 504.442
• InChiKey: GRDHQWBQPQWUOG-BIWBGZITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.3
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  269
• 氢给体数：
  11
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  α-槐糖 单水合物 、 β-D-glucose 1-phosphate 在 recombinant maltose phosphorylase Bsel₂₀₅₆ from Bacillus selenitireducens MLS₁₀ 作用下， 以 aq. buffer 为溶剂， 以40%的产率得到
  参考文献：
  名称：

  Identification of Bacillus selenitireducens MLS10 maltose phosphorylase possessing synthetic ability for branched α-d-glucosyl trisaccharides

  摘要：

  We discovered an inverting maltose phosphorylase (Bsel2056) belonging to glycoside hydrolase family 65 from Bacillus selenitireducens MLS10, which possesses synthetic ability for alpha-D-glucosyl disaccharides and trisaccharides through the reverse phosphorolysis with beta-D-glucose 1-phosphate as the donor. Bsel2056 showed the flexibility for monosaccharide acceptors with alternative C2 substituent (2-amino-2-deoxy-D-glucose, 2-deoxy-D-arabino-hexose, 2-acetamido-2-deoxy-D-glucose, D-mannose), resulting in production of 1,4-alpha-D-glucosyl disaccharides with strict regioselectivity. In addition, Bsel2056 synthesized two maltose derivatives possessing additional D-glucosyl residue bound to C2 position of the D-glucose residue at the reducing end, 1,4-alpha-D-glucopyranosyl-[1,2-alpha-D-glucopyranosyl]-D-glucose and 1,4-alpha-D-glucopyranosyl-[1,2-beta-D-glucopyranosyl]-D-glucose, from 1,2-alpha-D-glucopyranosyl-D-glucose (kojibiose) and 1,2-beta-D-glucopyranosyl-D-glucose (sophorose), respectively, as the acceptors. These results suggested that Bsel2056 possessed a binding space to accommodate the bulky C2 substituent of D-glucose. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.07.014

文献信息

• Identification of Bacillus selenitireducens MLS10 maltose phosphorylase possessing synthetic ability for branched α-d-glucosyl trisaccharides
  作者：Takanori Nihira、Yuka Saito、Motomitsu Kitaoka、Ken’ichi Otsubo、Hiroyuki Nakai

  DOI：10.1016/j.carres.2012.07.014

  日期：2012.10

  We discovered an inverting maltose phosphorylase (Bsel2056) belonging to glycoside hydrolase family 65 from Bacillus selenitireducens MLS10, which possesses synthetic ability for alpha-D-glucosyl disaccharides and trisaccharides through the reverse phosphorolysis with beta-D-glucose 1-phosphate as the donor. Bsel2056 showed the flexibility for monosaccharide acceptors with alternative C2 substituent (2-amino-2-deoxy-D-glucose, 2-deoxy-D-arabino-hexose, 2-acetamido-2-deoxy-D-glucose, D-mannose), resulting in production of 1,4-alpha-D-glucosyl disaccharides with strict regioselectivity. In addition, Bsel2056 synthesized two maltose derivatives possessing additional D-glucosyl residue bound to C2 position of the D-glucose residue at the reducing end, 1,4-alpha-D-glucopyranosyl-[1,2-alpha-D-glucopyranosyl]-D-glucose and 1,4-alpha-D-glucopyranosyl-[1,2-beta-D-glucopyranosyl]-D-glucose, from 1,2-alpha-D-glucopyranosyl-D-glucose (kojibiose) and 1,2-beta-D-glucopyranosyl-D-glucose (sophorose), respectively, as the acceptors. These results suggested that Bsel2056 possessed a binding space to accommodate the bulky C2 substituent of D-glucose. (C) 2012 Elsevier Ltd. All rights reserved.