xylopyranosyl β-(1,4)-glucopyranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: xylopyranosyl β-(1,4)-glucopyranose
• 英文别名: βGlc-(1->4)-Xyl；4-O-beta-D-xylopyranosyl-D-glucopyranose；(3R,4R,5S,6R)-6-(hydroxymethyl)-5-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxane-2,3,4-triol
• 化学式: C₁₁H₂₀O₁₀
• 分子量: 312.274
• InChiKey: GMIAWATVTRICKZ-IVBFVFLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  169
• 氢给体数：
  7
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  xylopyranosyl β-(1,4)-glucopyranose 在 cyclodextrin phosphorylase (EC 2.4.1.49) 、 MOPS buffer 作用下， 反应 264.0h， 生成 β-D-glucopyranosyl-(1->4)-β-D-xylopyranosyl-(1->4)-β-D-xylopyranosyl-(1->4)-D-glucopyranose
  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
• 作为产物：
  描述：

  (2S,3R,4S,5R)-2-((2R,3R,4S,5R,6R)-4,5,6-Tris-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3,4,5-triol 以89%的产率得到
  参考文献：
  名称：

  SEN, ASISH K.;BANERJI, NILIMA, INDIAN J. CHEM. B , 28,(1989) N0, C. 818-823

  摘要：

  DOI：

文献信息

• Carbohydrate esterases of family 2 are 6-<i>O</i>-deacetylases
  作者：Evangelos Topakas、Sarantos Kyriakopoulos、Peter Biely、Ján Hirsch、Christina Vafiadi、Paul Christakopoulos

  DOI：10.1016/j.febslet.2009.11.095

  日期：2010.2.5

  regioselectivity is different from that of typical acetylxylan esterases (AcXEs). In aqueous medium saturated with vinyl acetate, the CE‐2 enzymes catalyzed transacetylation to the same position, i.e., to the primary hydroxyl group of mono‐ and disaccharides. Xylose and xylooligosaccharides did not serve as acetyl group acceptors, therefore the CE‐2 enzymes appear to be 6‐O‐deacetylases.

  测试了来自腐生细菌 Cellvibrio japonicus 和热纤梭菌（碳水化合物酯酶 (CE) 家族 2 的成员）的三种乙酰酯酶 (AcE) 对一系列模型底物的活性，包括部分乙酰化的葡萄糖苷、甘露糖苷和吡喃木糖苷。所有三种酶都表现出对己醛糖 6 位脱乙酰化的强烈偏好。这种区域选择性不同于典型的乙酰木聚糖酯酶 (AcXE)。在醋酸乙烯饱和的水性介质中，CE-2 酶催化乙酰基转移到相同的位置，即到单糖和二糖的伯羟基。木糖和低聚木糖不作为乙酰基受体，因此 CE-2 酶似乎是 6-O-脱乙酰酶。
• SEN, ASISH K.;BANERJI, NILIMA, INDIAN J. CHEM. B , 28,(1989) N0, C. 818-823
  作者：SEN, ASISH K.、BANERJI, NILIMA

  DOI：——

  日期：——
• 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.