木四糖 | 22416-58-6

• 物质功能分类: 分析化学 - 标准品
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 木四糖
• 英文名称: β-D-Xylp-(1-4)-β-D-Xylp-(1-4)-β-D-Xylp-(1-4)-β-D-Xyl
• 英文别名: xylotetraose；xylotetrose；Xylotetraose；Xylotetrose；(2R,3R,4R)-4-[(2S,3R,4R,5R)-5-[(2S,3R,4R,5R)-3,4-dihydroxy-5-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxyoxan-2-yl]oxy-2,3,5-trihydroxypentanal
• CAS: 22416-58-6
• 化学式: C₂₀H₃₄O₁₇
• 分子量: 546.48
• InChiKey: JVZHSOSUTPAVII-MESLASACSA-N

物化性质

• 熔点：
  219-220°C
• 比旋光度：
  -57.8 º (c=1% in H2O)
• 沸点：
  907.1±65.0 °C(Predicted)
• 密度：
  1.72±0.1 g/cm3(Predicted)
• 溶解度：
  DMSO（少许）、水（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  -7.4
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  275
• 氢给体数：
  10
• 氢受体数：
  17

制备方法与用途

生物活性方面，xylotetraose 是木聚糖（xylan）水解的产物。木聚糖是一种多糖，主要由纤维素连接的β-D-木糖单元组成。Xylotetraose 可用于酶生化分析。

反应信息

• 作为反应物：
  描述：

  木四糖 在 polyethylenimine-coated Selenomonas ruminantium β-xylosidase immobilized on glyoxyl agarose 、 水 作用下， 以 aq. acetate buffer 为溶剂， 反应 2.08h， 生成 木二糖
  参考文献：
  名称：

  β-xylosidase from Selenomonas ruminantium: Immobilization, stabilization, and application for xylooligosaccharide hydrolysis

  摘要：

  The tetrameric -xylosidase from Selenomonas ruminantium is very stable in alkaline pH allowing it to easily immobilize by multipoint covalent attachments on highly activated glyoxyl agarose gels. Initial immobilization resulted only in slight stabilization in relation to the free enzyme, since involvement of all subunits was not achieved. Coating the catalyst with aldehyde-dextran or polyethylenimine, fully stabilized the quaternary structure of the enzyme rendering much more stabilization to the biocatalyst. The catalyst coated with polyethylenimine of molecular weight 1300 is the most stable one exhibiting an interesting half-life of more than 10 days at pH 5.0 and 50 degrees C, being, therefore, 240-fold more stable than free enzyme. Optimum activity was observed in the pH range 4.0-6.0 and at 55 degrees C. The catalyst retained its side activity against p-nitrophenyl -l-arabinofuranoside and it was inhibited by xylose and glucose. Kinetic parameters with p-nitrophenyl -d-xylopyranoside as substrate were V-max 0.20mol.min(-1)mgprot.(-1), K-m 0.45mM, K-cat 0.82s(-1), and K-cat/K-m 1.82s(-1)mM(-1). Xylose release was observed from the hydrolysis of xylooligosaccharides with a decrease in the rate of xylose release by increasing substrate chain-length. Due to the high thermostability and the complete stability after five reuse cycles, the applicability of this biocatalyst in biotechnological processes, such as for the degradation of lignocellulosic biomass, is highly increased.

  DOI：

  10.1080/10242422.2016.1247817
• 作为产物：
  描述：

  xylohexaose 在 polyethylenimine-coated Selenomonas ruminantium β-xylosidase immobilized on glyoxyl agarose 、 水 作用下， 以 aq. acetate buffer 为溶剂， 反应 2.08h， 生成 木四糖
  参考文献：
  名称：

  β-xylosidase from Selenomonas ruminantium: Immobilization, stabilization, and application for xylooligosaccharide hydrolysis

  摘要：

  The tetrameric -xylosidase from Selenomonas ruminantium is very stable in alkaline pH allowing it to easily immobilize by multipoint covalent attachments on highly activated glyoxyl agarose gels. Initial immobilization resulted only in slight stabilization in relation to the free enzyme, since involvement of all subunits was not achieved. Coating the catalyst with aldehyde-dextran or polyethylenimine, fully stabilized the quaternary structure of the enzyme rendering much more stabilization to the biocatalyst. The catalyst coated with polyethylenimine of molecular weight 1300 is the most stable one exhibiting an interesting half-life of more than 10 days at pH 5.0 and 50 degrees C, being, therefore, 240-fold more stable than free enzyme. Optimum activity was observed in the pH range 4.0-6.0 and at 55 degrees C. The catalyst retained its side activity against p-nitrophenyl -l-arabinofuranoside and it was inhibited by xylose and glucose. Kinetic parameters with p-nitrophenyl -d-xylopyranoside as substrate were V-max 0.20mol.min(-1)mgprot.(-1), K-m 0.45mM, K-cat 0.82s(-1), and K-cat/K-m 1.82s(-1)mM(-1). Xylose release was observed from the hydrolysis of xylooligosaccharides with a decrease in the rate of xylose release by increasing substrate chain-length. Due to the high thermostability and the complete stability after five reuse cycles, the applicability of this biocatalyst in biotechnological processes, such as for the degradation of lignocellulosic biomass, is highly increased.

  DOI：

  10.1080/10242422.2016.1247817

文献信息

• Structure of an l-arabino-d-xylan from the bark of Cinnamomum zeylanicum
  作者：D. Channe Gowda、Chitra Sarathy

  DOI：10.1016/0008-6215(87)80062-9

  日期：1987.9

  d -xylose in the molar ratio 1.6:1.0. Partial hydrolysis furnished oligosaccharides which were characterised as α- d -Xyl p -(1→3)- d -Ara, β- d Xyl p -(1→4)- d -Xyl, β- d -Xyl p -(1→4)-β- d -Xyl p -(1→4)- d -Xyl, β- d -Xyl p -(1→4)-β- d -Xyl p -(1→4)-β- d -Xyl p -Xyl p -(1→4)- d -Xyl, xylopentaose, and xylohexaose. Mild acid hydrolysis of the arabinoxylan gave a degraded polysaccharide consisting of

  摘要从桂皮中提取的阿拉伯木聚糖由1-阿拉伯糖和d-木糖组成，摩尔比为1.6：1.0。部分水解得到的寡糖的特征是α-d -Xyl p-（1→3）-d -Ara，β-d Xyl p-（1→4）-d -Xyl，β-d -Xyl p-（1 →4）-β-d -Xyl p-（1→4）-d -Xyl，β-d -Xyl p-（1→4）-β-d -Xyl p-（1→4）-β-d -Xyl p -Xyl p-（1→4）-d -Xyl，木基戊糖和木六糖。阿拉伯糖基木聚糖的轻度酸水解产生了由1-阿拉伯糖（8％）和d-木糖酶（92％）组成的降解的多糖。甲基化分析表明降解的多糖为线性（1→4）连接的d -xlan，其中一些吡喃吡喃糖基残基在O-2或O-3处被1-阿拉伯呋喃糖基取代。
• A surface-based mass spectrometry method for screening glycosidase specificity in environmental samples
  作者：Ana Beloqui、Antonio Sanchez-Ruiz、Manuel Martin-Lomas、Niels-Christian Reichardt

  DOI：10.1039/c2cc16537f

  日期：——

  A new surface-based MALDI-Tof-MS glycosyl hydrolase assay has been developed in which lipid-tagged oligosaccharides, representing defined fragments of major plant cell wall polysaccharides, are immobilized via hydrophobic interactions on an alkylthiol functionalised gold sample plate and employed in the functional screening of several purified enzymes, environmental samples and saliva.

  一种基于表面的新型MALDI-Tof-MS糖苷酶测定法已经开发出来，其中脂标记寡糖（代表主要植物细胞壁多糖的特定片段）通过疏水相互作用固定在烷基硫醇官能化的金样品板上，用于几种纯化酶、环境样品和唾液的功能筛选。
• OLIGOSACCHARIDES OF XYLOSE FROM WHEAT STRAW HEMICELLULOSE
  作者：C. T. Bishop

  DOI：10.1139/v55-124

  日期：1955.6.1

  A series of oligosaccharides were prepared by autoclaving wheat straw hemicellulose at 120 °C. in distilled water. The di- to the hepta-saccharide inclusive were shown to be members of the (1 → 4)-β-D-xylopyranose series. The octasaccharide was shown to be doubly branched. Certain aspects of the structure of wheat straw hemicellulose are discussed on the basis of these results.

  一系列寡糖在120℃的蒸汽压力锅中，使用蒸馏水从小麦秸秆半纤维素中制备而成。其中二糖到七糖都属于(1→4)-β-D-木聚糖系列。八糖则被证明是双分支的。基于这些结果，讨论了小麦秸秆半纤维素的某些结构方面。
• A β-xylosidase from cell wall of maize: Purification, properties and its use in hydrolysis of plant cell wall
  作者：Yejun Han、Hongzhang Chen

  DOI：10.1016/j.molcatb.2010.01.004

  日期：2010.5

  To study the potential of plant glycoside hydrolase for hemicelluloses hydrolysis, a beta-xylosidase with molecular weight of 68.5 kDa was purified from the maize during senescent stage. The optimal conditions for the beta-xylosidase were 37 degrees C and pH 4.5. In absence of substrate, the beta-xylosidase was comparatively stable at 37 degrees C and pH 4.5-5.5. At the optimum condition, the K-m and k(cat) values of the beta-xylosidase against p-nitrophenyl-xyloside were 2.5 mM and 6.5 s(-1), respectively. The enzyme activity was promoted by LiCl, CaCl2, MnCl2, MgCl2, KCl. and NaCl, however severely inhibited by CuCl2, ZnCl2, AgNO3, HgCl2, and NiCl2. The purified beta-xylosidase was active against xylobiose, xylotriose, xylotetraose, and xylopentaose. In hydrolysis of corn stover hemicellulose, the xylose production increased by 94.9% and 140% when Trichoderma reesei hemicellulase supplemented with purified beta-xylosidase and crude cell wall proteins of corn stover, respectively. The biochemical characterization of the maize beta-xylosidase makes it a promising candidate enzyme additive for hemicelluloses hydrolysis. (C) 2010 Elsevier By. All rights reserved.
• Characterization of a recombinant multifunctional glycoside hydrolase family 3 β-xylosidase/α-l-arabinofuranosidase/β-glucosidase from Cellulosimicrobium cellulans sp. 21
  作者：Ye Yuan、Yanbo Hu、Han Zhang、Jiayi Leng、Fan Li、Xuesong Zhao、Juan Gao、Yifa Zhou

  DOI：10.1016/j.molcatb.2016.06.002

  日期：2016.9

  A multifunctional beta-xylosidase/alpha-L-arabinofuranosidase/beta-glucosidase gene (ccxyl3a) belonging to glycoside hydrolase family 3 (GH3) was cloned from Cellulosimicrobium cellulans sp. 21 and expressed in Escherichia coli BL21 (DE3). The molecular mass of recombinant CcXyl3A was estimated to be approximately 95 kDa. With p-nitrophenyl-beta-D-xyloside (pNP beta Xyl) as a substrate, the purified protein, presented an optimal pH of 8.5 and an optimal temperature of 45 degrees C. Moreover, CcXyl3A was activated in the presence of the metals K+ and Na+. Purified CcXyl3A demonstrated multifunctional activities on pNP beta Xyl, p-nitrophenyl-beta-D-glucoside (pNP beta G1c), and p-nitrophenyl-alpha-L-arabinofuranoside (pNP alpha Araf). The greatest catalytic activity were found on pNP beta Xyl followed by pNPaAraf and pNP beta G1c, respectively. Using xylooligosaccharides as substrate, CcXyl3A completely hydrolyzed xylobiose, xylotriose, xylotetraose and xylohexaose, xylose was the sole product. In addition, CcXyl3A synergistically acted with Thermomyces lanuginosus xylanase in the degradation of beechwood xylan, released xyloses from intermediate xylooligosaccharides produced by T. lanuginosus xylanase. To date, this is the first report to demonstrate the cloning and characterization of a multifunctional GH3 enzyme in C. cellulans that may have applications in hemicellulose degradation. (C) 2016 Elsevier B.V. All rights reserved.