β-D-mannopyranosyl-(1→4)-β-D-mannopyranosyl-(1→4)-β-D-mannopyranosyl-(1→4)-β-D-mannopyranosyl-(1→4)-β-D-mannopyranosyl-(1→4)-D-mannopyranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-D-mannopyranosyl-(1→4)-β-D-mannopyranosyl-(1→4)-β-D-mannopyranosyl-(1→4)-β-D-mannopyranosyl-(1→4)-β-D-mannopyranosyl-(1→4)-D-mannopyranose
• 英文别名: β-(1,4)-D-mannohexose；1,4-β-D-mannoohexaose；mannohexaose；Mannohexaose；(2S,3S,4S,5S,6R)-2-[(2R,3S,4R,5S,6S)-6-[(2R,3S,4R,5S,6S)-6-[(2R,3S,4R,5S,6S)-6-[(2R,3S,4R,5S,6S)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(2R,3S,4R,5S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• 化学式: C₃₆H₆₂O₃₁
• 分子量: 990.87
• InChiKey: OCIBBXPLUVYKCH-KKQGKRJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -13.3
• 重原子数：
  67
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  506
• 氢给体数：
  20
• 氢受体数：
  31

反应信息

• 作为反应物：
  描述：

  β-D-mannopyranosyl-(1→4)-β-D-mannopyranosyl-(1→4)-β-D-mannopyranosyl-(1→4)-β-D-mannopyranosyl-(1→4)-β-D-mannopyranosyl-(1→4)-D-mannopyranose 在 recombinant Podospora anserina GH₂₆ mannanase A 、 recombinant Podospora anserina GH₅ mannanase A 作用下， 以 aq. acetate buffer 为溶剂， 反应 1.0h， 生成 mannotriose
  参考文献：
  名称：

  Structural and Biochemical Analyses of Glycoside Hydrolase Families 5 and 26 β-(1,4)-Mannanases from Podospora anserina Reveal Differences upon Manno-oligosaccharide Catalysis

  摘要：

  The microbial deconstruction of the plant cell wall is a key biological process that is of increasing importance with the development of a sustainable biofuel industry. The glycoside hydrolase families GH5 (PaMan5A) and GH26 (PaMan26A) endo-beta-1,4-mannanases from the coprophilic ascomycete Podospora anserina contribute to the enzymatic degradation of lignocellulosic biomass. In this study, P. anserina mannanases were further subjected to detailed comparative analysis of their substrate specificities, active site organization, and transglycosylation capacity. Although PaMan5A displays a classical mode of action, PaMan26A revealed an atypical hydrolysis pattern with the release of mannotetraose and mannose from mannopentaose resulting from a predominant binding mode involving the -4 subsite. The crystal structures of PaMan5A and PaMan26A were solved at 1.4 and 2.85 angstrom resolution, respectively. Analysis of the PaMan26A structure supported strong interaction with substrate at the -4 subsite mediated by two aromatic residues Trp-244 and Trp-245. The PaMan26A structure appended to its family 35 carbohydrate binding module revealed a short and proline-rich rigid linker that anchored together the catalytic and the binding modules.

  DOI：

  10.1074/jbc.m113.459438
• 作为产物：
  描述：

  β-D-mannopyranosyl-(1→4)-β-D-mannopyranosyl-(1→4)-2-O-acetyl-β-D-mannopyranosyl-(1→4)-2-O-acetyl-β-D-mannopyranosyl-(1→4)-β-D-mannopyranosyl-(1→4)-D-mannopyranose 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 2.0h， 以84%的产率得到β-D-mannopyranosyl-(1→4)-β-D-mannopyranosyl-(1→4)-β-D-mannopyranosyl-(1→4)-β-D-mannopyranosyl-(1→4)-β-D-mannopyranosyl-(1→4)-D-mannopyranose
  参考文献：
  名称：

  β-（1→4）连接的寡甘露糖和部分乙酰化衍生物的合成及生物活性

  摘要：

  β-（1→4）-连接的六至八甘露糖及其部分乙酰化衍生物的合成可通过以下方式有效地进行：使用β-选择性糖基化组装适当的寡聚片段，然后在合成途径的后期进行葡萄糖到甘露糖的差向异构化。在该研究过程中，我们还观察到由于乙酰基的分子内迁移，2- O-乙酰化的低聚甘露糖与3- O-乙酰化的异构体在平衡中共存。研究了合成的低聚甘露糖和部分乙酰化衍生物的生物活性，以鉴定诱导细胞因子的最小寡聚体，如从霍山石end提取的多糖中所示。

  DOI：

  10.1021/jo4005266

文献信息

• Synthesis and bioassay of β-(1,4)-D-mannans as potential agents against Alzheimer's disease
  作者：Ru-wei Jiang、Xiao-guang Du、Xuan Zhang、Xin Wang、Ding-yu Hu、Tao Meng、Yue-lei Chen、Mei-yu Geng、Jing-kang Shen

  DOI：10.1038/aps.2013.104

  日期：2013.12

  Oligomannurarate 971 derived from a marine plant has shown neuroprotective effects. In this study we synthesized a series of truncated derivatives of the oligosaccharide, and investigated the effect of these derivatives against Aβ peptide toxicity in vitro. The sulfoxide method was applied to synthesize the derivatives. SH-SY5Y human neuroblastoma cells were treated with Aβ1-40 (2 μmol/L), and the cell viability was detected using a CCK8 assay. A series of β-(1,4)-D-mannosyl oligosaccharide, ranging from the disaccharide to the hexasaccharide, were synthesized. Addition of 10 μmol/L β-(1,4)-D-mannobiose 6, β-(1,4)-D-mannotriose 9 or β-(1,4)-D-mannotetraose 12 in SH-SY5Y cells significantly attenuated Aβ1-40-induced toxicity. The efficacies were similar to those caused by 10 μmol/L oligomannurarate 971 or alzhemed. Other oligosaccharides including oligomaltoses and oligocelluloses were less active. Synthetic homogeneous short chain β-(1,4)-D-mannans shows neuroprotective effect against Aβ peptide toxicity similar to that of heterogeneous oligomannurarate 971 and alzhemed.

  来源于海洋植物的低聚甘露糖酸盐971显示出神经保护效果。在本研究中，我们合成了一系列低聚糖的截短衍生物，并研究了这些衍生物对Aβ肽毒性的抑制作用。采用亚磺酸方法合成了这些衍生物。用Aβ1-40（2 μmol/L）处理SH-SY5Y人神经母细胞瘤细胞，并通过CCK8检测细胞活力。合成了一系列β-(1,4)-D-甘露糖低聚糖，范围从二糖到六糖。在SH-SY5Y细胞中添加10 μmol/L β-(1,4)-D-甘露二糖6、β-(1,4)-D-甘露三糖9或β-(1,4)-D-甘露四糖12显著减轻了Aβ1-40诱导的毒性。这些效果与10 μmol/L低聚甘露糖酸盐971或阿尔兹海默药物的效果相似。其他低聚糖如低聚麦芽糖和低聚纤维素的活性较低。合成的均匀短链β-(1,4)-D-甘露糖表现出对Aβ肽毒性的神经保护效果，类似于非均匀的低聚甘露糖酸盐971和阿尔兹海默药物。
• Structural and Biochemical Analyses of Glycoside Hydrolase Families 5 and 26 β-(1,4)-Mannanases from Podospora anserina Reveal Differences upon Manno-oligosaccharide Catalysis
  作者：Marie Couturier、Alain Roussel、Anna Rosengren、Philippe Leone、Henrik Stålbrand、Jean-Guy Berrin

  DOI：10.1074/jbc.m113.459438

  日期：2013.5

  The microbial deconstruction of the plant cell wall is a key biological process that is of increasing importance with the development of a sustainable biofuel industry. The glycoside hydrolase families GH5 (PaMan5A) and GH26 (PaMan26A) endo-beta-1,4-mannanases from the coprophilic ascomycete Podospora anserina contribute to the enzymatic degradation of lignocellulosic biomass. In this study, P. anserina mannanases were further subjected to detailed comparative analysis of their substrate specificities, active site organization, and transglycosylation capacity. Although PaMan5A displays a classical mode of action, PaMan26A revealed an atypical hydrolysis pattern with the release of mannotetraose and mannose from mannopentaose resulting from a predominant binding mode involving the -4 subsite. The crystal structures of PaMan5A and PaMan26A were solved at 1.4 and 2.85 angstrom resolution, respectively. Analysis of the PaMan26A structure supported strong interaction with substrate at the -4 subsite mediated by two aromatic residues Trp-244 and Trp-245. The PaMan26A structure appended to its family 35 carbohydrate binding module revealed a short and proline-rich rigid linker that anchored together the catalytic and the binding modules.
• Synthesis and Bioactivity of β-(1→4)-Linked Oligomannoses and Partially Acetylated Derivatives
  作者：Keiichiro Ohara、Chih-Chien Lin、Pei-Jung Yang、Wei-Ting Hung、Wen-Bin Yang、Ting-Jen Rachel Cheng、Jim-Min Fang、Chi-Huey Wong

  DOI：10.1021/jo4005266

  日期：2013.7.5

  The synthesis of β-(1→4)-linked hexa- to octamannoses and their partially acetylated derivatives was efficiently carried out by assembly of appropriate oligomeric fragments using β-selective glucosylation followed by gluco to manno epimerization at a late stage of the synthetic pathway. In the course of this study, we also observed that 2-O-acetylated oligomannoses coexisted in equilibrium with the

  β-（1→4）-连接的六至八甘露糖及其部分乙酰化衍生物的合成可通过以下方式有效地进行：使用β-选择性糖基化组装适当的寡聚片段，然后在合成途径的后期进行葡萄糖到甘露糖的差向异构化。在该研究过程中，我们还观察到由于乙酰基的分子内迁移，2- O-乙酰化的低聚甘露糖与3- O-乙酰化的异构体在平衡中共存。研究了合成的低聚甘露糖和部分乙酰化衍生物的生物活性，以鉴定诱导细胞因子的最小寡聚体，如从霍山石end提取的多糖中所示。