β-D-xylopyranosyl-(1 <*> 4)-tris<β-D-xylopyranosyl-(1 <*> 4)>-D-xylopyranose | 83009-08-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-D-xylopyranosyl-(1 <*> 4)-tris<β-D-xylopyranosyl-(1 <*> 4)>-D-xylopyranose
• 英文别名: 1,4-β-D-xylopentaose；xylopentaose；(2S,3R,4S,5R)-2-[(3R,4R,5R,6S)-6-[(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]oxy-4,5-dihydroxyoxan-3-yl]oxyoxane-3,4,5-triol
• CAS: 83009-08-9；139327-84-7
• 化学式: C₂₅H₄₂O₂₁
• 分子量: 678.596
• InChiKey: LFFQNKFIEIYIKL-BLPAIIJASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -8.6
• 重原子数：
  46
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  326
• 氢给体数：
  12
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  β-D-xylopyranosyl-(1 <*> 4)-tris<β-D-xylopyranosyl-(1 <*> 4)>-D-xylopyranose 在 Xn-A enzime 、 Xn-B enzyme 作用下， 反应 5.0h， 生成 D-(+)-xylobiose
  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：

  O-(2,3-di-O-acetyl-4-O-benzyl-β-D-xylopyranosyl)-(1->4)-O-(2,3-di-O-acetyl-β-D-xylopyranosyl)-(1->4)-1,2,3-tri-O-acetyl-β-D-xylopyranose 在 palladium on activated charcoal sodium methylate 、 氰化汞 作用下， 以 吡啶 、 甲醇 、 丙酮 、 乙腈 为溶剂， 反应 22.0h， 生成 β-D-xylopyranosyl-(1 <*> 4)-tris<β-D-xylopyranosyl-(1 <*> 4)>-D-xylopyranose
  参考文献：
  名称：

  系统合成（1→4）-β-d-木糖寡糖的方法

  摘要：

  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。

  DOI：

  10.1016/s0008-6215(00)81074-5

文献信息

• Synthesis of (1 → 4)-β-d-xylo-oligosaccharides of dp 4–10 by a blockwise approach
  作者：Kenichi Takeo、Yasushi Ohguchi、Rumi Hasegawa、Shinichi Kitamura

  DOI：10.1016/0008-6215(95)00259-6

  日期：1995.12

  xylopyranosyl-(1-->4) -2.3-di - O-(4-methylbenzoyl)-1-thio-beta-D-xylopyranoside (18) in 70% yield. Coupling of 18 with benzyl alcohol afforded the disaccharide benzyl beta-glycoside, which was O-dechloroacetylated to provide methyl 2,3-di-O-(4-methylbenzoyl)-beta-D-xylopyranosyl-(1-->4)-2,3-di-O-(4- methylbenzoyl)-1-thio-beta-D-xylopyranoside (20). A homologous series of (1-->4)-beta-D-xylo-oligosaccharides

  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，
• 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.
• Correlation of the conformational structure and catalytic activity of the highly thermostable xylanase of <i>Thermomyces lanuginosus</i> PC7S1T
  作者：Carla Lieko Della Torre、Rosemeire Aparecida Silva-Lucca、Rodrigo da Silva Ferreira、Luciana Andrade Luz、Maria Luiza Vilela Oliva、Marina Kimiko Kadowaki

  DOI：10.1080/10242422.2021.1950696

  日期：2023.3.4
• 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。