methyl 2-(2,3,4,6-tetra-O-acetyl-1-O-α-D-mannopyranosyl)acetate | 1096143-52-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 2-(2,3,4,6-tetra-O-acetyl-1-O-α-D-mannopyranosyl)acetate
• 英文别名: methyl 2-[(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)oxy]acetate
• CAS: 1096143-52-0
• 化学式: C₁₇H₂₄O₁₂
• 分子量: 420.37
• InChiKey: ZNFDYVFTESVWMQ-ZUOZUFPHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.74
• 重原子数：
  29.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  149.96
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  methyl 2-(2,3,4,6-tetra-O-acetyl-1-O-α-D-mannopyranosyl)acetate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以80%的产率得到methyl 2-(1-O-α-D-mannopyranosyl)acetate
  参考文献：
  名称：

  Design of new enzyme stabilizers inspired by glycosides of hyperthermophilic microorganisms

  摘要：

  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.

  DOI：

  10.1016/j.carres.2008.08.030
• 作为产物：
  描述：

  羟乙酸甲酯 、 2,3,4,6-四-O-乙酰基-α-D-吡喃甘露糖 三氯乙酰亚胺酯 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以69%的产率得到methyl 2-(2,3,4,6-tetra-O-acetyl-1-O-α-D-mannopyranosyl)acetate
  参考文献：
  名称：

  Design of new enzyme stabilizers inspired by glycosides of hyperthermophilic microorganisms

  摘要：

  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.

  DOI：

  10.1016/j.carres.2008.08.030

文献信息

• Solvent- and catalyst-free transamidations of unprotected glycosyl carboxamides
  作者：Fouzia Ouadah Bensalah、Abed Bil、Karlo Wittine、Salima Bellahouel、David Lesur、Dean Markovic、Sylvain Laclef

  DOI：10.1039/c9ob02096a

  日期：——

  The transamidation reactions of unprotected mono- and disaccharidic carboxamides with various primary and secondary arylic, heterocyclic or aliphatic amines are described. This new method is green and atom efficient and gives good to high yields. Notably, the conditions do not require either a solvent or a catalyst and give ammonia as a single by-product. The described coupling reaction is compatible

  描述了未保护的单和二糖羧酰胺与各种伯和仲芳族，杂环或脂族胺的氨基转移反应。这种新方法具有绿色环保和原子效率高的优点。明显地，该条件不需要溶剂或催化剂，并且给出氨作为单一副产物。所描述的偶联反应与多种官能团相容，并且被用于合成各种糖苷衍生物和生物学上相关的糖脂。提出了一种可能的反应机理，涉及起始羧酰胺的分子间氢键活化。