O-β-D-Glucopyranosyl-(1->4)-O-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: O-β-D-Glucopyranosyl-(1->4)-O-β-D-mannopyranosyl-(1->4)-D-mannopyranose
• 英文别名: Glc(b1-4)Man(b1-4)Man；(2S,3R,4S,5S,6R)-2-[(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-6-(hydroxymethyl)oxane-3,4,5-triol
• 化学式: C₁₈H₃₂O₁₆
• 分子量: 504.442
• InChiKey: FYGDTMLNYKFZSV-RQYJIIQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.9
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  269
• 氢给体数：
  11
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 生成 4-O-β-D-glucopyranosyl-D-mannose 、 O-β-D-mannopyranosyl-(1->4)-D-mannopyranose 、 O-β-D-Glucopyranosyl-(1->4)-O-β-D-mannopyranosyl-(1->4)-D-mannopyranose 、 β-Manp-(1->4)-[α-Galp-(1->6)]-Man
  参考文献：
  名称：

  Chemical characterization of the immunomodulating polysaccharide of Aloe vera L.

  摘要：

  The polysaccharide isolated by alcohol precipitation of Aloe vera mucilaginous gel was found to have a Man:Glc:Gal: GalA:Fuc:Ara:Xyl ratio of 120:9:6:3:2:2:1 with traces of Rha and GlcA. Linkage analysis of the endo-(1 -> 4)-beta-D-mannanase-treated sample yielded Manp-(1 ->(similar to 26%), 4-Manp(similar to 53%), 2,4-Manp (similar to 3%), 3,4-Manp (similar to 1%), 4,6-Manp (similar to 1%), 4-Glcp (similar to 5%), 4-Xylp (similar to 1%), Xylp-(1 ->(similar to 2%), Galp-(1 ->(similar to 5%), and traces of 4,6-Galp and 3,6-Galp. Hydrolysis with strong acids produced a mixture of short oligosaccharides and an acid-resistant fraction containing greater relative fractions of Manp-(1 -> Araf-(1 -> Xylp-(1 -> and 4-Xylp than the bulk polysaccharide. NMR analysis of oligosaccharides generated by endo-(1 -> 4)-beta-D-mannanase and acid hydrolysis showed the presence of di-, tri-, and tetrasaccharides of 4-beta-Manp, beta-Glcp-(1 -> 4)-Man, beta-Glcp-(1 -> 4)-beta-Manp-(1 -> 4)-Man, and beta-Manp-(1 -> 4)-[alpha-Galp-(1 -> 6)]-Man, consistent with a backbone containing alternating and -> 4)-beta-Manp-(1 -> and -> 4)-beta- Glcp(1 -> residues in a similar to 15:1 ratio. Analysis of the sample treated sequentially with endo-(1 -> 4)-beta-D-mannanase and alpha-D-galactosidase showed that the majority of alpha-Galp-(1 -> residues were linked to O-2, O-3, or O-6 of -> 4)-beta-Manp-(1 -> residues, with similar to 16 -> 4)-beta-Manp-(1 -> residues between side chains. Our data provide direct evidence of a previously proposed glucomannan backbone, but draw into question previously proposed side-chain structures. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2005.02.016

文献信息

• Polysaccharides ofEremurus. XV. Structure of the glucomannan ofEremurus lactiflorus
  作者：A. Dzhumamuratova、D. A. Rakhimov、E. S. Kondratenko

  DOI：10.1007/bf00579414

  日期：1982.11
• Chemical characterization of the immunomodulating polysaccharide of Aloe vera L.
  作者：Jimmy Tai-Nin Chow、David A. Williamson、Kenneth M. Yates、Warren J. Goux

  DOI：10.1016/j.carres.2005.02.016

  日期：2005.5

  The polysaccharide isolated by alcohol precipitation of Aloe vera mucilaginous gel was found to have a Man:Glc:Gal: GalA:Fuc:Ara:Xyl ratio of 120:9:6:3:2:2:1 with traces of Rha and GlcA. Linkage analysis of the endo-(1 -> 4)-beta-D-mannanase-treated sample yielded Manp-(1 ->(similar to 26%), 4-Manp(similar to 53%), 2,4-Manp (similar to 3%), 3,4-Manp (similar to 1%), 4,6-Manp (similar to 1%), 4-Glcp (similar to 5%), 4-Xylp (similar to 1%), Xylp-(1 ->(similar to 2%), Galp-(1 ->(similar to 5%), and traces of 4,6-Galp and 3,6-Galp. Hydrolysis with strong acids produced a mixture of short oligosaccharides and an acid-resistant fraction containing greater relative fractions of Manp-(1 -> Araf-(1 -> Xylp-(1 -> and 4-Xylp than the bulk polysaccharide. NMR analysis of oligosaccharides generated by endo-(1 -> 4)-beta-D-mannanase and acid hydrolysis showed the presence of di-, tri-, and tetrasaccharides of 4-beta-Manp, beta-Glcp-(1 -> 4)-Man, beta-Glcp-(1 -> 4)-beta-Manp-(1 -> 4)-Man, and beta-Manp-(1 -> 4)-[alpha-Galp-(1 -> 6)]-Man, consistent with a backbone containing alternating and -> 4)-beta-Manp-(1 -> and -> 4)-beta- Glcp(1 -> residues in a similar to 15:1 ratio. Analysis of the sample treated sequentially with endo-(1 -> 4)-beta-D-mannanase and alpha-D-galactosidase showed that the majority of alpha-Galp-(1 -> residues were linked to O-2, O-3, or O-6 of -> 4)-beta-Manp-(1 -> residues, with similar to 16 -> 4)-beta-Manp-(1 -> residues between side chains. Our data provide direct evidence of a previously proposed glucomannan backbone, but draw into question previously proposed side-chain structures. (c) 2005 Elsevier Ltd. All rights reserved.