β-D-glucopyranosyl-(1->4)-β-D-xylopyranosyl-(1->4)-β-D-glucopyranosyl-(1->4)-D-xylopyranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-D-glucopyranosyl-(1->4)-β-D-xylopyranosyl-(1->4)-β-D-glucopyranosyl-(1->4)-D-xylopyranose
• 英文别名: Glc(b1-4)Xyl(b1-4)Glc(b1-4)Xyl；(2S,3R,4S,5S,6R)-2-[(3R,4R,5R,6S)-6-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(3R,4R,5R)-4,5,6-trihydroxyoxan-3-yl]oxyoxan-3-yl]oxy-4,5-dihydroxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• 化学式: C₂₂H₃₈O₁₉
• 分子量: 606.532
• InChiKey: JBLHEFOHLPBELM-AZVRYTAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -7.8
• 重原子数：
  41
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  307
• 氢给体数：
  12
• 氢受体数：
  19

反应信息

• 作为产物：
  描述：

  4-O-β-D-glucosyl-D-xylose 在 cyclodextrin phosphorylase (EC 2.4.1.49) 、 MOPS buffer 作用下， 反应 144.0h， 生成 β-D-glucopyranosyl-(1->4)-β-D-xylopyranosyl-(1->4)-β-D-glucopyranosyl-(1->4)-D-xylopyranose
  参考文献：
  名称：

  Enzymatic synthesis of a library of β-(1→4) hetero- d-glucose and d-xylose-based oligosaccharides employing cellodextrin phosphorylase

  摘要：

  Enzymatic synthesis was attempted of six trisaccharides and 14 tetrasaccharides comprising beta-(1-->4)-linked D-glucose and D-xylose residues, using cellodextrin phosphorylase (CDP, EC 2.4.1.49) as the enzyme catalyst, with alpha-D-glucose 1-phosphate (1) alpha-D-xylose 1-phosphate (2) as the donor substrates, and cellobiose (3), xylobiose (4), betaGlc-(l-->4)-Xyl (5), or betaXyl-(1-->4)-Glc (6) as the acceptor substrates. All enzymatic reactions were performed at pH 7.0 and the products purified by gel-filtration chromatography. We successfully synthesized all six hetero-trisaccharides and 10 of the 14 possible hetero-tetrasaccharides. It was not found possible to synthesize the four tetrasaccharides with a Xyl-->Glc sequence at their non-reducing ends employing this method. The stereochemistries of the isolated products were assessed by analysis of their 2D NMR spectra (DQF-COSY, TOCSY, HSQC, HMBC). confirming that all of the glycosidic bonds in the products were beta-(1-->4) linkages. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00314-8

文献信息

• Enzymatic synthesis of a library of β-(1→4) hetero- d-glucose and d-xylose-based oligosaccharides employing cellodextrin phosphorylase
  作者：Keiko Shintate、Motomitsu Kitaoka、Yeon-Kye Kim、Kiyoshi Hayashi

  DOI：10.1016/s0008-6215(03)00314-8

  日期：2003.9

  Enzymatic synthesis was attempted of six trisaccharides and 14 tetrasaccharides comprising beta-(1-->4)-linked D-glucose and D-xylose residues, using cellodextrin phosphorylase (CDP, EC 2.4.1.49) as the enzyme catalyst, with alpha-D-glucose 1-phosphate (1) alpha-D-xylose 1-phosphate (2) as the donor substrates, and cellobiose (3), xylobiose (4), betaGlc-(l-->4)-Xyl (5), or betaXyl-(1-->4)-Glc (6) as the acceptor substrates. All enzymatic reactions were performed at pH 7.0 and the products purified by gel-filtration chromatography. We successfully synthesized all six hetero-trisaccharides and 10 of the 14 possible hetero-tetrasaccharides. It was not found possible to synthesize the four tetrasaccharides with a Xyl-->Glc sequence at their non-reducing ends employing this method. The stereochemistries of the isolated products were assessed by analysis of their 2D NMR spectra (DQF-COSY, TOCSY, HSQC, HMBC). confirming that all of the glycosidic bonds in the products were beta-(1-->4) linkages. (C) 2003 Elsevier Ltd. All rights reserved.