3-O-β-D-xylopyranosyl-4-O-β-D-xylopyranosyl-D-xylose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-β-D-xylopyranosyl-4-O-β-D-xylopyranosyl-D-xylose
• 英文别名: O-β-D-xylopyranosyl-(1->3)-O-β-D-xylopyranosyl-(1->4)-D-xylopyranose；3²-β-xylopyranosylxylobiose；β-D-Xylp-(1->3)-β-D-Xylp-(1->4)-D-Xylp；2³-β-D-xylosylxylobiose；β-(1→3)-xylosylxylobiose；Xyl(b1-3)Xyl(b1-4)Xyl；(2S,3R,4S,5R)-2-[(2S,3R,4S,5R)-3,5-dihydroxy-2-[(3R,4R,5R)-4,5,6-trihydroxyoxan-3-yl]oxyoxan-4-yl]oxyoxane-3,4,5-triol
• 化学式: C₁₅H₂₆O₁₃
• 分子量: 414.364
• InChiKey: QIBJLUWGMJRJEQ-QABWTVKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.6
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  208
• 氢给体数：
  8
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  3-O-β-D-xylopyranosyl-4-O-β-D-xylopyranosyl-D-xylose 在 Bifidobacterium adolescentis β-D-xylosidase BAD0423 作用下， 以 aq. phosphate buffer 为溶剂， 反应 1.0h， 生成 D-(+)-xylobiose 、 beta-D-吡喃木糖
  参考文献：
  名称：

  Identification of a Key Enzyme for the Hydrolysis of β-(1→3)-Xylosyl Linkage in Red Alga Dulse Xylooligosaccharide from Bifidobacterium Adolescentis

  摘要：

  红藻多糖具有独特的木聚糖，由线性β-(1→3)/β-(1→4)-木聚糖键组成。我们之前从红藻中制备了特征性木聚糖（DX3，(β-(1→3)-木聚糖-木二糖)）。在这项研究中，我们评估了DX3对肠道细菌的益生作用。虽然Bacteroides sp.和Bifidobacterium adolescentis利用了DX3，但与β-(1→4)-木三糖（X3）相比，Bacteroides Ksp.生长较慢，但B. adolescentis的生长与X3类似。因此，我们旨在找到B. adolescentis中关键的DX3水解酶。通过生物信息学分析，从糖苷水解酶家族43中选择了两个酶（BAD0423：亚家族12和BAD0428：亚家族11），并在大肠杆菌中表达。BAD0423以2988 mU/mg的特异活性水解DX3中的β-(1→3)-木聚糖键，产生木糖（X1）和木二糖（X2），对X2和X3的活性较低。BAD0428对X2和X3具有较高的活性，产生X1，而BAD0428对DX3的活性为1298 mU/mg，产生X1。BAD0423和BAD0428的协同水解作用发现，在组合中产生X1作为主要产物。从酶的特性来看，X3的水解由一个酶BAD0428完成，而DX3的水解需要两个以上的酶。

  DOI：

  10.3390/md18030174
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 Streptomyces β-xylanase 作用下， 生成 3-O-β-D-xylopyranosyl-4-O-β-D-xylopyranosyl-D-xylose 、 3²-β-xylobiosylxylobiose 、 2²-β-xylopyranosylxylobiose
  参考文献：
  名称：

  Structure of Hardwood Xylan and Specificity ofStreptomyces β-Xylanase toward the Xylan

  摘要：

  Three kinds of xylo-oligosaccharides having structures of 32-β-xylosylxylobiose, 32-β-xylobiosylxylobiose, and 22-β-xylobiosylxylobiose were isolated from an enzymatic hydrolysate of hardwood xylan with Streptomyces β-xylanase. The structures suggest that the hardwood xylan has both (1 → 2)- and (1 → 3)-β-d-xylopyranosyl linkages in the structure, and the specificity of Streptomyces β-xylanase toward the stubs is similar to that toward glucuronic acid stubs, but is somewhat different from that toward arabinose and xylosylarabinose stubs.

  DOI：

  10.1271/bbb.58.2068

文献信息

• Win, Maung; Kamiyama, Yoshi; Matsuo, Masaru, Agricultural and Biological Chemistry, 1988, vol. 52, # 5, p. 1151 - 1158
  作者：Win, Maung、Kamiyama, Yoshi、Matsuo, Masaru、Yasui, Tsuneo

  DOI：——

  日期：——
• Identification of a Key Enzyme for the Hydrolysis of β-(1→3)-Xylosyl Linkage in Red Alga Dulse Xylooligosaccharide from Bifidobacterium Adolescentis
  作者：Manami Kobayashi、Yuya Kumagai、Yohei Yamamoto、Hajime Yasui、Hideki Kishimura

  DOI：10.3390/md18030174

  日期：——

  Red alga dulse possesses a unique xylan, which is composed of a linear β-(1→3)/β-(1→4)-xylosyl linkage. We previously prepared characteristic xylooligosaccharide (DX3, (β-(1→3)-xylosyl-xylobiose)) from dulse. In this study, we evaluated the prebiotic effect of DX3 on enteric bacterium. Although DX3 was utilized by Bacteroides sp. and Bifidobacterium adolescentis, Bacteroides Ksp. grew slowly as compared with β-(1→4)-xylotriose (X3) but B. adolescentis grew similar to X3. Therefore, we aimed to find the key DX3 hydrolysis enzymes in B. adolescentis. From bioinformatics analysis, two enzymes from the glycoside hydrolase family 43 (BAD0423: subfamily 12 and BAD0428: subfamily 11) were selected and expressed in Escherichia coli. BAD0423 hydrolyzed β-(1→3)-xylosyl linkage in DX3 with the specific activity of 2988 mU/mg producing xylose (X1) and xylobiose (X2), and showed low activity on X2 and X3. BAD0428 showed high activity on X2 and X3 producing X1, and the activity of BAD0428 on DX3 was 1298 mU/mg producing X1. Cooperative hydrolysis of DX3 was found in the combination of BAD0423 and BAD0428 producing X1 as the main product. From enzymatic character, hydrolysis of X3 was completed by one enzyme BAD0428, whereas hydrolysis of DX3 needed more than two enzymes.

  红藻多糖具有独特的木聚糖，由线性β-(1→3)/β-(1→4)-木聚糖键组成。我们之前从红藻中制备了特征性木聚糖（DX3，(β-(1→3)-木聚糖-木二糖)）。在这项研究中，我们评估了DX3对肠道细菌的益生作用。虽然Bacteroides sp.和Bifidobacterium adolescentis利用了DX3，但与β-(1→4)-木三糖（X3）相比，Bacteroides Ksp.生长较慢，但B. adolescentis的生长与X3类似。因此，我们旨在找到B. adolescentis中关键的DX3水解酶。通过生物信息学分析，从糖苷水解酶家族43中选择了两个酶（BAD0423：亚家族12和BAD0428：亚家族11），并在大肠杆菌中表达。BAD0423以2988 mU/mg的特异活性水解DX3中的β-(1→3)-木聚糖键，产生木糖（X1）和木二糖（X2），对X2和X3的活性较低。BAD0428对X2和X3具有较高的活性，产生X1，而BAD0428对DX3的活性为1298 mU/mg，产生X1。BAD0423和BAD0428的协同水解作用发现，在组合中产生X1作为主要产物。从酶的特性来看，X3的水解由一个酶BAD0428完成，而DX3的水解需要两个以上的酶。
• Structure of Hardwood Xylan and Specificity of<i>Streptomyces β</i>-Xylanase toward the Xylan
  作者：Shigeki Yoshida、Tetsuo Ono、Noriki Matsuo、Isao Kusakabe

  DOI：10.1271/bbb.58.2068

  日期：1994.1

  Three kinds of xylo-oligosaccharides having structures of 32-β-xylosylxylobiose, 32-β-xylobiosylxylobiose, and 22-β-xylobiosylxylobiose were isolated from an enzymatic hydrolysate of hardwood xylan with Streptomyces β-xylanase. The structures suggest that the hardwood xylan has both (1 → 2)- and (1 → 3)-β-d-xylopyranosyl linkages in the structure, and the specificity of Streptomyces β-xylanase toward the stubs is similar to that toward glucuronic acid stubs, but is somewhat different from that toward arabinose and xylosylarabinose stubs.