O-β-D-Mannopyranosyl(1->4)-O-β-D-mannopyranosyl(1->4)-D-glucopyranose | 6401-81-6

• 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)-D-glucopyranose
• 英文别名: Man(b1-4)Man(b1-4)Glc；(2S,3S,4S,5S,6R)-2-[(2R,3S,4R,5S,6S)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 6401-81-6；17659-52-8；19141-16-3；20702-55-0；52485-13-9；69429-19-2；80446-86-2；80446-87-3；94799-30-1；94799-74-3；113158-51-3；118396-93-3；121153-20-6；133267-59-1；142185-35-1
• 化学式: C₁₈H₃₂O₁₆
• 分子量: 504.442
• InChiKey: FYGDTMLNYKFZSV-UJFCUHIISA-N

物化性质

• 沸点：
  865.2±65.0 °C(Predicted)
• 密度：
  1.80±0.1 g/cm3(Predicted)

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

• 作为反应物：
  描述：

  O-β-D-Mannopyranosyl(1->4)-O-β-D-mannopyranosyl(1->4)-D-glucopyranose 、 乙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 16.0h， 生成 O-(2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl)-(1->4)-O-(2,3,6-tri-O-acetyl-β-D-mannopyranosyl)-(1->4)-1,2,3,6-tetra-O-acetyl-D-glucopyranose
  参考文献：
  名称：

  三和四己糖苷小麦面粉神经酰胺的立体选择性全合成。

  摘要：

  小麦糖鞘脂，O-（β-D-甘露吡喃糖基-[（1-> 4）-O-（β-D-甘露吡喃糖基）] nO-（β-D-吡喃葡萄糖基）-（1-> 1）-立体选择性地合成了（2S，3S，4R）-4-羟基-N-十四烷酰基鞘氨醇（n = 1和2）当4-O-乙酰基-2,3,6-三-O-苄基时，硅酸银促进了糖基化使用-α-D-甘露酰吡喃糖基溴来延长聚糖链，该聚糖链随后通过三氯乙酰亚胺酸酯方法与神经酰胺衍生物偶联。

  DOI：

  10.1271/bbb.57.698
• 作为产物：
  描述：

  benzyl O-(4-O-acetyl-2,3,6-tri-O-benzyl-β-D-mannopyranosyl)-(1->4)-O-(2,3,6-tri-O-benzyl-β-D-mannopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 在 palladium on activated charcoal 甲酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 1.0h， 生成 O-β-D-Mannopyranosyl(1->4)-O-β-D-mannopyranosyl(1->4)-D-glucopyranose
  参考文献：
  名称：

  三和四己糖苷小麦面粉神经酰胺的立体选择性全合成。

  摘要：

  小麦糖鞘脂，O-（β-D-甘露吡喃糖基-[（1-> 4）-O-（β-D-甘露吡喃糖基）] nO-（β-D-吡喃葡萄糖基）-（1-> 1）-立体选择性地合成了（2S，3S，4R）-4-羟基-N-十四烷酰基鞘氨醇（n = 1和2）当4-O-乙酰基-2,3,6-三-O-苄基时，硅酸银促进了糖基化使用-α-D-甘露酰吡喃糖基溴来延长聚糖链，该聚糖链随后通过三氯乙酰亚胺酸酯方法与神经酰胺衍生物偶联。

  DOI：

  10.1271/bbb.57.698

文献信息

• Hydrolysis of konjac glucomannan by Trichoderma reesei mannanase and endoglucanases Cel7B and Cel5A for the production of glucomannooligosaccharides
  作者：Atte Mikkelson、Hannu Maaheimo、Terhi K. Hakala

  DOI：10.1016/j.carres.2013.02.012

  日期：2013.5

  In this paper we describe the enzymatic hydrolysis of konjac glucomannan for the production of glucomannooligosaccharides using purified Trichoderma reesei mannanase, endoglucanases EGI (Tr Cel7b) and EGII (Tr Cel5a). Hydrolysis with each of the three enzymes produced a different pattern of oligosaccharides. Mannanase was the most selective of the three enzymes in the hydrolysis of konjac mannan and over 99% of the formed oligosaccharides had mannose as their reducing end pyranosyl unit. Tr Cel5A hydrolysate shared similarities with mannanase and Tr Cel7B hydrolysates and the enzyme had the lowest substrate specificity of the studied enzymes. The hydrolysate of Tr Cel7B contained a series of oligosaccharides with non-reducing end mannose (M) and reducing end glucose (G) (MG, MMG, MMMG, and MMMMG). These oligosaccharides were isolated from the hydrolysate by size exclusion chromatography in relatively high purity (86-95%) and total yield (23% of substrate). The isolated oligosaccharides were characterized using acid hydrolysis and HPAEC-PAD (carbohydrate composition), HPLC-RI and HPAEC-MS (to determine the DP of purified oligosaccharides), enzymatic hydrolysis (determination of non-reducing end carbohydrate) and NMR (both 1D and 2D, to verify structure and purity of purified compounds). Hydrolysis of konjac mannan with a specific enzyme, such as T. reesei Cel7B or mannanase, followed by fractionation with SEC offers the possibility to produce glucomannooligosaccharides with defined structure. The isolated oligosaccharides can be utilised as analytical standards, for determination of bioactivity of oligosaccharides with defined structure or as substrates for defining substrate specificity of novel carbohydrate hydrolyzing enzymes. (C) 2013 Elsevier Ltd. All rights reserved.
• Stereoselective Total Synthesis of Tri- and Tetrahexoside Wheat Flour Ceramide
  作者：Katsuya Koike、Masato Mori、Yukishige Ito、Yoshiaki Nakahara、Tomoya Ogawa

  DOI：10.1271/bbb.57.698

  日期：1993.1

  The wheat glycosphingolipids, O-(beta-D-mannopyranosyl-[(1-->4)-O-(beta-D-mannopyranosyl)]n-O-(beta-D -glucopyranosyl)-(1-->1)-(2S,3S,4R)-4-hydroxy-N-tetracosanoylsphingan ine (n = 1 and 2), were stereoselectively synthesized. Silver silicate promoted glycosylation when 4-O-acetyl-2,3,6-tri-O-benzyl-alpha-D-mannopyranosyl bromide was used for elongating the glycan chains, which were latter coupled

  小麦糖鞘脂，O-（β-D-甘露吡喃糖基-[（1-> 4）-O-（β-D-甘露吡喃糖基）] nO-（β-D-吡喃葡萄糖基）-（1-> 1）-立体选择性地合成了（2S，3S，4R）-4-羟基-N-十四烷酰基鞘氨醇（n = 1和2）当4-O-乙酰基-2,3,6-三-O-苄基时，硅酸银促进了糖基化使用-α-D-甘露酰吡喃糖基溴来延长聚糖链，该聚糖链随后通过三氯乙酰亚胺酸酯方法与神经酰胺衍生物偶联。