O-β-D-mannopyranosyl-(1-4)-O-β-D-mannopyranosyl-(1-4)-O-β-D-mannopyranosyl-(1-4)-D-mannopyranose | 1263-76-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-β-D-mannopyranosyl-(1-4)-O-β-D-mannopyranosyl-(1-4)-O-β-D-mannopyranosyl-(1-4)-D-mannopyranose
• 英文别名: O-β-D-mannopyranosyl-(1-4)-O-β-D-mannopyranosyl-(1-4)-O-β-D-mannopyranosyl-(1-4)-D-mannose；β-D-Manp(1->4)-β-D-Manp(1->4)-β-D-Manp(1->4)-D-Manp；β-(1,4)-D-mannotetraose；1,4-β-mannotetraose；β-D-mannotetraose；mannotetraose；(2S,3S,4S,5S,6R)-2-[(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-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 1263-76-9；13086-23-2；20702-56-1；69429-16-9；133574-70-6
• 化学式: C₂₄H₄₂O₂₁
• 分子量: 666.585
• InChiKey: LUEWUZLMQUOBSB-MHJOMNRISA-N

物化性质

• 沸点：
  1030.9±65.0 °C(predicted)
• 密度：
  1.83±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)
• 碰撞截面：
  234.12 Ų [M+Na]+ [CCS Type: DT, Method: stepped-field]

计算性质

• 辛醇/水分配系数(LogP)：
  -9
• 重原子数：
  45
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  348
• 氢给体数：
  14
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  O-β-D-mannopyranosyl-(1-4)-O-β-D-mannopyranosyl-(1-4)-O-β-D-mannopyranosyl-(1-4)-D-mannopyranose 在 recombinant Podospora anserina GH₅ mannanase A 作用下， 以 aq. acetate buffer 为溶剂， 反应 1.0h， 生成 O-β-D-mannopyranosyl-(1->4)-D-mannopyranose 、 D-甘露糖
  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：

  在 palladium hydroxide, 20 wt% on carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以18 mg的产率得到O-β-D-mannopyranosyl-(1-4)-O-β-D-mannopyranosyl-(1-4)-O-β-D-mannopyranosyl-(1-4)-D-mannopyranose
  参考文献：
  名称：

  Synthesis and bioassay of β-(1,4)-D-mannans as potential agents against Alzheimer's disease

  摘要：

  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。

  DOI：

  10.1038/aps.2013.104

文献信息

• Characterisation of the oligosaccharides produced on hydrolysis of galactomannan with β-d-mannase
  作者：Barry V. McCleary、Elizabeth Nurthen、François R. Taravel、Jean-Paul Joseleau

  DOI：10.1016/0008-6215(83)88038-0

  日期：1983.7

  Treatment of hot-water-soluble carob galactomannan with β- d -mannanases from A. niger or lucerne seed affords an array of d -galactose-containing β- d -mannosaccharides as well as β- d -manno-biose, -triose, and -tetraose (lucerne-seed enzyme only). The d -galactose-containing β- d -mannosaccharides of d.p. 3–9 produced by A. niger β- d -mannanase have been characterised, using enzymic, n.m.r., and chemical

  摘要用黑曲霉或卢塞恩种子中的β-d-甘露聚糖酶处理热水可溶性角豆半乳甘露聚糖，可得到一系列含d-半乳糖的β-d-甘露糖糖以及β-d-甘露糖二糖，三糖，和-四糖（仅限于琉森种子酶）。黑曲霉β-d-甘露聚糖酶产生的dp 3-9的含d-半乳糖的β-d-甘露糖已通过酶，核磁共振和化学技术表征为6 1-α-d-半乳糖基-β -d-甘露二糖，6 1-α-d-半乳糖基-β-d-甘露三糖，6 3，6 4-di-α-d-半乳糖基-β-d-甘露糖半乳糖（唯一的七糖）和6 3，6 4-di-α-d-半乳糖基-β-d-甘露糖己糖，6 4，6 5-di-α-d-半乳糖基-β-d-甘露糖己糖和6 1，6 3，6 4-tri-α- d-半乳糖基-β-d-甘露半乳糖（唯一的八糖）。还鉴定了四种九糖。没有五糖和六糖。卢塞恩种子β-d-甘露聚糖酶产生相同的支链三糖，四糖和七糖，以及五糖和六糖，其特征为6 1-α-d-半乳糖基-β-d-甘露糖，6
• 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 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。