1-O-(2-glyceryl)-α-D-mannopyranoside | 40593-14-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: 1-O-(2-glyceryl)-α-D-mannopyranoside
• 英文别名: (β,β'-dihydroxy-isopropyl)-α-D-mannopyranoside；(β,β'-Dihydroxy-isopropyl)-α-D-mannopyranosid；2-O-alpha-d-mannopyranosyl glycerol；(2S,3S,4S,5S,6R)-2-(1,3-dihydroxypropan-2-yloxy)-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 40593-14-4
• 化学式: C₉H₁₈O₈
• 分子量: 254.237
• InChiKey: AQTKXCPRNZDOJU-DFTQBPQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.5
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  140
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-硝基苯甲酰氯 、 1-O-(2-glyceryl)-α-D-mannopyranoside 在 吡啶 作用下， 生成 [β,β'-bis-(4-nitro-benzoyloxy)-isopropyl]-[tetrakis-O-(4-nitro-benzoyl)-α-D-mannopyranoside]
  参考文献：
  名称：

  寡糖中糖苷键的构型：III.O-α-D-吡喃甘露糖基-(1 → 2)-O-α-D-甘露糖基-(1 → 2)-D-甘露糖

  摘要：

  Saccharomycesrouxii 甘露聚糖乙酰化后获得的三糖显示为 O-α-D-吡喃甘露糖基-(1 → 2)-O-α-D-吡喃甘露糖基-(1 → 2)-D-甘露糖。甲基化和四乙酸铅氧化技术定义了糖苷键的位置。这两个键的构型是通过使用两种新的降解方法确定的，这些方法产生 2-O-α-D-吡喃甘露糖基-D-甘露糖和 2-O-α-D-吡喃甘露糖基-甘油，每一种都含有一个糖苷键母体三糖。

  DOI：

  10.1139/v57-037
• 作为产物：
  描述：

  2-O-α-D-Mannopyranosyl-D-mannit 在 lead(IV) acetate 、 溶剂黄146 作用下， 生成 1-O-(2-glyceryl)-α-D-mannopyranoside
  参考文献：
  名称：

  寡糖中糖苷键的构型：II．通过将二糖还原为 2-O-糖基-甘油

  摘要：

  还原性吡喃己糖二糖通过一系列氧化和还原作用降解，产生 2-O-糖基-甘油，其构型根据 Hudson 的定义进行分配。例如，麦芽糖用 2 摩尔四乙酸铅处理得到 2-O-α-D-吡喃葡萄糖基-D-赤藓糖；后者被还原为相应的醇，依次用 1 摩尔四乙酸铅氧化生成 2-O-α-D-吡喃葡萄糖基-L-甘油醛，第二次还原生成 2-O-α-D-吡喃葡萄糖基-甘油。纤维二糖通过相同的反应序列转化为 2-O-β-D-吡喃葡萄糖基甘油。其他含有 D-吡喃葡萄糖非还原性末端单元的还原性二糖也可以被降解以得到这些异头甘油衍生物中的一种或另一种，其身份确定了原始二糖中糖苷键的构型。这对异头 2-OD-吡喃半乳糖基甘油由天然存在的 α-异头物提供，产物 o...

  DOI：

  10.1139/v56-234

文献信息

• Design of new enzyme stabilizers inspired by glycosides of hyperthermophilic microorganisms
  作者：Tiago Q. Faria、Ana Mingote、Filipa Siopa、Rita Ventura、Christopher Maycock、Helena Santos

  DOI：10.1016/j.carres.2008.08.030

  日期：2008.12

  In response to stressful conditions like supra-optimal salinity in the growth medium or temperature, many microorganisms accumulate low-molecular-mass organic compounds known as compatible solutes. In contrast with mesophiles that accumulate neutral or zwitterionic compounds, the solutes of hyperthermophiles are typically negatively charged. (2R)-2-(alpha-D-Mannopyranosyl)glycerate (herein abbreviated as mannosylglycerate) is one of the most widespread solutes among thermophilic and hyperthermophilic prokaryotes. In this work, several molecules chemically related to mannosylglycerate were namely (2S)-2-(1-O-alpha-D-mannopyranosyl)propionate, 2-(1-O-alpha-D-mannopyranosyl)acetate, synthesized, (2R)-2-(1-O-alpha-D-glucopyranosyl)glycerate and 1-O-(2-glyceryl)-alpha-D-mannopyraiioside. The effectiveness of the newly synthesized compounds for the protection of model enzymes against heat-induced denaturation, aggregation and inactivation was evaluated, using differential scanning calorimetry, light scattering and measurements of residual activity. For comparison, the protection induced by natural compatible solutes, either neutral (e.g., trehalose, glycerol, ectoine) or negatively charged (di-myo-inositol-1,3 '-phosphate and diglycerol phosphate), was assessed. Phosphate, sulfate, acetate and KCl were also included in the assays to rank the solutes and new compounds in the Hofmeister series. The data demonstrate the superiority of charged organic solutes as thermo-stabilizers of enzymes and strongly support the view that the extent of protein stabilization rendered by those solutes depends clearly on the specific solute/enzyme examined. The relevance of these findings to our knowledge on the mode of action of charged solutes is discussed. (C) 2008 Elsevier Ltd. All rights reserved.
• THE CONFIGURATION OF GLYCOSIDIC LINKAGES IN OLIGOSACCHARIDES: II. BY DEGRADATION OF REDUCING DISACCHARIDES TO 2-<i>O</i>-GLYCOSYL-GLYCEROLS
  作者：A. J. Charlson、P. A. J. Gorin、A. S. Perlin

  DOI：10.1139/v56-234

  日期：1956.12.1

  degraded by employing a series of oxidations and reductions to yield 2-O-glycosyl-glycerols, configurations of which are assigned according to Hudson's definition. Maltose, for example, treated with 2 moles of lead tetraacetate gives 2-O-α-D-glucopyranosyl-D-erythrose; the latter is reduced to the corresponding alcohol, which is oxidized in turn with 1 mole of lead tetraacetate to give 2-O-α-D-gluco

  还原性吡喃己糖二糖通过一系列氧化和还原作用降解，产生 2-O-糖基-甘油，其构型根据 Hudson 的定义进行分配。例如，麦芽糖用 2 摩尔四乙酸铅处理得到 2-O-α-D-吡喃葡萄糖基-D-赤藓糖；后者被还原为相应的醇，依次用 1 摩尔四乙酸铅氧化生成 2-O-α-D-吡喃葡萄糖基-L-甘油醛，第二次还原生成 2-O-α-D-吡喃葡萄糖基-甘油。纤维二糖通过相同的反应序列转化为 2-O-β-D-吡喃葡萄糖基甘油。其他含有 D-吡喃葡萄糖非还原性末端单元的还原性二糖也可以被降解以得到这些异头甘油衍生物中的一种或另一种，其身份确定了原始二糖中糖苷键的构型。这对异头 2-OD-吡喃半乳糖基甘油由天然存在的 α-异头物提供，产物 o...
• THE CONFIGURATION OF GLYCOSIDIC LINKAGES IN OLIGOSACCHARIDES: III. <i>O</i>-α-<scp>D</scp>-MANNOPYRANOSYL-(1 → 2)-<i>O</i>-α-<scp>D</scp>-MANNOPYRANOSYL-(1 → 2)-<scp>D</scp>-MANNOSE
  作者：P. A. J. Gorin、A. S. Perlin

  DOI：10.1139/v57-037

  日期：1957.3.1

  Methylation and lead tetraacetate Oxidation techniques define the positions of the glycosidic linkages. The configurations of the two linkages are determined through use of two novel degradative methods which yield 2-O-α-D-mannopyranosyl-D-mannose and 2-O-α-D-mannopyranosyl-glycerol, each containing one of the glycosidic linkages of the parent trisaccharide.

  Saccharomycesrouxii 甘露聚糖乙酰化后获得的三糖显示为 O-α-D-吡喃甘露糖基-(1 → 2)-O-α-D-吡喃甘露糖基-(1 → 2)-D-甘露糖。甲基化和四乙酸铅氧化技术定义了糖苷键的位置。这两个键的构型是通过使用两种新的降解方法确定的，这些方法产生 2-O-α-D-吡喃甘露糖基-D-甘露糖和 2-O-α-D-吡喃甘露糖基-甘油，每一种都含有一个糖苷键母体三糖。