xylotetraose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: xylotetraose
• 英文别名: (2S,3R,4S,5R)-2-[(3R,4R,5R,6S)-6-[(3R,4R,5R,6S)-4,5-dihydroxy-6-[(3R,4R,5R)-4,5,6-trihydroxyoxan-3-yl]oxyoxan-3-yl]oxy-4,5-dihydroxyoxan-3-yl]oxyoxane-3,4,5-triol
• 化学式: C₂₀H₃₄O₁₇
• 分子量: 546.48
• InChiKey: KPTPSLHFVHXOBZ-BIKCPUHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -7.1
• 重原子数：
  37
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  267
• 氢给体数：
  10
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  xylotetraose 在 sodium tetrahydroborate 、 Xn-B enzyme 作用下， 以 水 为溶剂， 反应 3.0h， 生成 O-BETA-D-吡喃木糖基-(1-4)-O-BETA-D-吡喃木糖基-(1-4)-D-木糖醇
  参考文献：
  名称：

  Mitsuishi, Yasushi; Yamanobe, Takashi; Yagisawa, Mitsuo, Agricultural and Biological Chemistry, 1988, vol. 52, # 4, p. 921 - 928

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-(1<*>4)-2,3-di-O-acetyl-1-thio-β-D-xylopyranoside 在 palladium on activated charcoal 吡啶 、 甲醇 、 N-碘代丁二酰亚胺 、 4 A molecular sieve 、 氢气 、 sodium methylate 、 silver trifluoromethanesulfonate 、 二正丁基氧化锡 、 硫脲 、 氯乙酰氯 作用下， 以 甲醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， -20.0~25.0 ℃ 、101.33 kPa 条件下， 反应 9.34h， 生成 xylotetraose
  参考文献：
  名称：

  dp 4-10的（1→4）-β-d-木糖寡糖的合成

  摘要：

  二丁基氧化锡介导的1-硫代-β-木糖苷甲基的区域选择性氯乙酰化，然后用4-甲基苯甲酰氯-吡啶处理产物，得到甲基4-O-氯乙酰基-2,3-二-O-（4-甲基苯甲酰基） -β-D-吡喃并吡喃糖基-（1→4）-2.3-二-O-（4-甲基苯甲酰基）-1-硫代β-D-吡喃并吡喃糖苷（18），收率为70％。将18与苄醇偶联得到二糖苄基β-糖苷，将其进行O-脱氯乙酰化，得到甲基2,3-二-O-（4-甲基苯甲酰基）-β-D-吡喃并吡喃糖基-（1→4）- 2,3-二-O-（4-甲基苯甲酰基）-1-硫代-β-D-吡喃吡喃糖苷（20）。通过使用20作为糖基受体，18，甲基1-硫代-甲基，以嵌段方式合成了从四糖到十糖的一系列同源（1-> 4）-β-D-木糖寡糖。 β-木糖甙五乙酸盐，

  DOI：

  10.1016/0008-6215(95)00259-6

文献信息

• An approach to the systematic synthesis of (1→4)-β-d-xylo-oligosaccharides
  作者：Ján Hirsch、Pavol Kováč、Eva Petráková

  DOI：10.1016/s0008-6215(00)81074-5

  日期：1982.8

  Abstract The first approach to a general synthesis of (1→4)-β- d -xylo-oligosaccharides is described. Thus, 1,2,3-tri- O -acetyl-4- O -benzyl-β- d -xylopyranose was treated with hydrogen bromide in dichloromethane to give the corresponding glycosyl bromide 3 , which was condensed with 1,2,3-tri- O -acetyl-β- d -xylopyranose. The β-linked disaccharide formed, bearing at O-4 of its non-reducing end the

  摘要描述了一般合成（1→4）-β-d-木糖寡糖的第一种方法。因此，用二氯甲烷中的溴化氢处理1,2,3-三-O-乙酰基-4-O-苄基-β-d-吡喃木糖，得到相应的糖基溴化物3，将其与1,2,3-缩合。三-O-乙酰基-β-d-吡喃木糖。形成的，在其非还原端的O-4处带有可选择性除去的苄基的β-连接的二糖进行氢解，得到无HO-4'的二糖亲核体21，再次用3处理。该反应序列再重复两次，将分离出的产物17-20脱保护，得到一系列同源的低级木糖寡糖（从二糖到五糖），因此证明了木糖寡糖分子逐步构建的可行性。缩合反应混合物中存在的相应的α-连接的低聚糖5-8也被分离出来并进行了表征。给出了六个同源序列的不同取代的（1→4）-d-木糖寡糖的13 CN.mr光谱特征。
• Enzymatically-synthesized xylo-oligosaccharides laurate esters as surfactants of interest
  作者：D. Gérard、T. Méline、M. Muzard、M. Deleu、R. Plantier-Royon、C. Rémond

  DOI：10.1016/j.carres.2020.108090

  日期：2020.9

  Lipase-catalyzed synthesis of xylo-oligosaccharides esters from pure xylobiose, xylotriose and xylotetraose in the presence of vinyl laurate was investigated. The influence of different experimental parameters such as the loading of lipase, the reaction duration or the use of a co-solvent was studied and the reaction conditions were optimized with xylobiose. Under the best conditions, a regioselective

  研究了在月桂酸乙烯酯的存在下，脂肪酶催化纯木糖，木三糖和木四糖合成木糖寡糖的酯。研究了不同实验参数的影响，如脂肪酶的负载量，反应持续时间或助溶剂的使用，并用木二糖优化了反应条件。在最佳条件下，发生区域选择性酯化反应，生成在非还原端木糖单元的OH-4上带有酰基链的单酯。已经评估了这些纯木糖寡糖脂肪酯的表面活性。它们显示出有趣的表面活性剂活性，其随甘氨酸部分的聚合度（DP）的不同而不同。
• Novel substrates for the automated and manual assay of endo -1,4-β-xylanase
  作者：David Mangan、Claudio Cornaggia、Agnija Liadova、Niall McCormack、Ruth Ivory、Vincent A. McKie、Aaron Ormerod、Barry V. McCleary

  DOI：10.1016/j.carres.2017.02.009

  日期：2017.6

  reproducible, automatable assay for this enzyme that is based on the use of a chemically defined substrate has not been described to date. Reported herein is a new enzyme coupled assay procedure, termed the XylX6 assay, that employs a novel substrate, namely 4,6-O-(3-ketobutylidene)-4-nitrophenyl-β-45-O-glucosyl-xylopentaoside. The development of the substrate and associated assay is discussed here and

  1，4-β-木聚糖内切酶（EC 3.2.1.8）被广泛应用于动物饲料，酿造，烘焙，生物燃料，洗涤剂和纸浆（纸）等行业。尽管其重要性，迄今为止尚未描述基于使用化学确定的底物对该酶进行快速，可靠，可再现，可自动化的测定。本文报道了一种新的酶偶联测定方法，称为XylX6测定法，其采用了新型底物，即4，6-O-（3-酮丁烯）-4-硝基苯基-β-45-O-葡糖基-木糖基opentaoside。本文讨论了底物和相关测定法的发展，并彻底研究了XylX6测定法与传统还原糖测定法获得的活性值之间的关系及其特异性和可重复性。
• A typical endo-xylanase from Streptomyces rameus L2001 and its unique characteristics in xylooligosaccharide production
  作者：Xiuting Li、E. Li、Yunping Zhu、Chao Teng、Baoguo Sun、Huanlu Song、Ran Yang

  DOI：10.1016/j.carres.2012.05.005

  日期：2012.10

  The activity of the extracellular xylanase produced by Streptomyces rameus L2001 against different xylans and xylooligosaccharides (XOS) was investigated. The main products of hydrolysis of birchwood xylan and oat-spelt xylan by the S. rameus L2001 xylanase were xylobiose (X2) and xylotriose (X3), suggesting that this is an endo-acting xylanase. This was confirmed by analysis of XOS degradation products. The enzyme hardly hydrolyzed X2 and X3, but hydrolyzed xylotetraose (X4) and xylopentaose (X5) producing mainly X2 and X3 through transglycosylation. Depending on the substrate, different quantities of reducing sugars were produced by the xylanase: 150 mg/g from corncob, 105 mg/g from bean culms, and 133 mg/g from bagasse. With the bagasse substrate, the xylanase yielded 2.36, 2.76, 2.03, and 2.17 mg/mL of X2, X3, X4, and X5, respectively. The structure of xylobiose and xylotriose from the hydrolysis of corncob xylan was identified by MS and NMR. The production of XOS from various agricultural wastes has potential industrial applications. This is the first report of XOS production by S. rameus L2001. (c) 2012 Elsevier Ltd. All rights reserved.
• Biochemical and catalytic properties of an endoxylanase purified from the culture filtrate of Sporotrichum thermophile
  作者：Petros Katapodis、Maria Vršanská、Dimitris Kekos、Wim Nerinckx、Peter Biely、Marc Claeyssens、Basil J Macris、Paul Christakopoulos

  DOI：10.1016/s0008-6215(03)00291-x

  日期：2003.9

  An endo-beta-1,4-xylanase (1,4-beta-D-xylan xylanoxydrolase, EC 3.2.1.8) present in culture filtrates of Sporotrichum thermophile ATCC 34628 was purified to homogeneity by Q-Sepharose Lind Sephacryl S-200 column chromatographies. The enzyme has a molecular mass of 25,000 Da, an isoelectric point of 6.7, and is optimally active at pH 5 and at 70 degreesC. Thin-layer chromatography (TLC) analysis showed that endo-xylanase liberates mainly xylose (Xyl) and xylobiose (Xyl,) from beechwood 4-O-methyl-D-glucuronoxylan, O-acetyl-4-O-methylglucuronoxylan and rhodymenan (a beta-(1-->4)-beta(1-->3)-xylan). Also, the enzyme releases an acidic xylo-oligosaccharide from 4-O-methyl-D-glucuronoxylan, and an isomeric xylotetraose and an isomeric xylopentaose from rhodymenan. Analysis of reaction mixtures by high performance liquid chromatography (HPLC) revealed that the enzyme cleaves preferentially the internal glycosidic bonds of xylooligosaccharides, [1-H-3]-xylooligosaccharides and xylan. The enzyme also hydrolyses the 4-methylumbelliferyl glycosides of beta-xylobiose and beta-xylotriose at the second glycosidic bond adjacent to the aglycon. The endoxylanase is not active on pNPX and pNPC. The enzyme mediates a decrease in the viscosity of xylan associated with a release of only small amounts of reducing sugar. The enzyme is irreversibly inhibited by series of omega-epoxyalkyl glycosides of D-Xylopyranose. The results suggest that the endoxylanase from S. thermophile has catalytic properties similar to the enzymes belonging to family 11. (C) 2003 Elsevier Ltd. All rights reserved.