4-O-β-D-glucosyl-D-xylose | 18354-18-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-O-β-D-glucosyl-D-xylose
• 英文别名: βXyl-(1->4)-Glc；β-D-GlcAp-(1->4)-Xyl；glucopyranosyl β-(1,4)-xylopyranose；β-Glcp-(1->4)-Xylp；4-O-beta-D-Glucopyranosyl-D-xylopyranose；(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[(3R,4R,5R)-4,5,6-trihydroxyoxan-3-yl]oxyoxane-3,4,5-triol
• CAS: 18354-18-2
• 化学式: C₁₁H₂₀O₁₀
• 分子量: 312.274
• InChiKey: VCTBNHVCBSUQPG-OOADKWOMSA-N

物化性质

• 沸点：
  613.7±55.0 °C(Predicted)
• 密度：
  1.74±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.1
• 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：

  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
• 作为产物：
  描述：

  D-木糖 、 对氟苯甲醇 在 recombinant cellobiose phosphorylase from Clostridium thermocellum ATCC₂₇₄₀₅ of glycoside hydrolase family 94 作用下， 反应 3.0h， 以30%的产率得到4-O-β-D-glucosyl-D-xylose
  参考文献：
  名称：

  通过使用热纤维梭菌中的纤维二糖磷酸化酶和纤维糊精磷酸化酶进行反向磷酸分解，有效合成化学酶寡糖。

  摘要：

  糖苷水解酶家族94的热纤梭菌ATCC27405转化纤维二糖磷酸化酶（CtCBP）和纤维糊精磷酸化酶（CtCDP）催化逆向磷酸分解，以57％和48％的α-d-葡萄糖1-磷酸葡萄糖作为供体与葡萄糖和纤维素生成糊精。纤维二糖分别作为受体。使用α-d-葡萄糖基1-氟化物作为供体可将CtCBP的产品收率提高到98％，将CtCDP的收率提高到68％。CtCBP显示出广泛的受体特异性，可从五个单糖形成具有β-（1→4）-区域选择性的β-葡萄糖基二糖，以及从三个（1→6）连接的具有β-（1→4）-区域选择性的支链β-葡萄糖基三糖二糖。CtCDP表现出严格的β-（1→4）-区域选择性和催化的三个β-连接的葡糖基二糖，纤维二糖，槐糖和拉米纳糖的线性扩链，而12个测试的单糖不是受体。通过NMR和ESI-MS的结构分析证实了两个β-葡萄糖基寡糖产物系列代表了新化合物，即β-D-吡喃葡萄糖基-[（1→4）-β-D-吡喃葡萄糖基]（n）-（1→2）

  DOI：

  10.1016/j.biochi.2010.07.013

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。
• Efficient chemoenzymatic oligosaccharide synthesis by reverse phosphorolysis using cellobiose phosphorylase and cellodextrin phosphorylase from Clostridium thermocellum
  作者：Hiroyuki Nakai、Maher Abou Hachem、Bent O. Petersen、Yvonne Westphal、Karin Mannerstedt、Martin J. Baumann、Adiphol Dilokpimol、Henk A. Schols、Jens Ø. Duus、Birte Svensson

  DOI：10.1016/j.biochi.2010.07.013

  日期：2010.12

  Inverting cellobiose phosphorylase (CtCBP) and cellodextrin phosphorylase (CtCDP) from Clostridium thermocellum ATCC27405 of glycoside hydrolase family 94 catalysed reverse phosphorolysis to produce cellobiose and cellodextrins in 57% and 48% yield from α-d-glucose 1-phosphate as donor with glucose and cellobiose as acceptor, respectively. Use of α-d-glucosyl 1-fluoride as donor increased product yields

  糖苷水解酶家族94的热纤梭菌ATCC27405转化纤维二糖磷酸化酶（CtCBP）和纤维糊精磷酸化酶（CtCDP）催化逆向磷酸分解，以57％和48％的α-d-葡萄糖1-磷酸葡萄糖作为供体与葡萄糖和纤维素生成糊精。纤维二糖分别作为受体。使用α-d-葡萄糖基1-氟化物作为供体可将CtCBP的产品收率提高到98％，将CtCDP的收率提高到68％。CtCBP显示出广泛的受体特异性，可从五个单糖形成具有β-（1→4）-区域选择性的β-葡萄糖基二糖，以及从三个（1→6）连接的具有β-（1→4）-区域选择性的支链β-葡萄糖基三糖二糖。CtCDP表现出严格的β-（1→4）-区域选择性和催化的三个β-连接的葡糖基二糖，纤维二糖，槐糖和拉米纳糖的线性扩链，而12个测试的单糖不是受体。通过NMR和ESI-MS的结构分析证实了两个β-葡萄糖基寡糖产物系列代表了新化合物，即β-D-吡喃葡萄糖基-[（1→4）-β-D-吡喃葡萄糖基]（n）-（1→2）
• 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.