2,3,4,6-tetra-O-acetyl-1-O-(2-glyceryl)-α-D-mannopyranoside | 213264-96-1

• 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: 2,3,4,6-tetra-O-acetyl-1-O-(2-glyceryl)-α-D-mannopyranoside
• CAS: 213264-96-1
• 化学式: C₁₇H₂₆O₁₂
• 分子量: 422.386
• InChiKey: XZWUDSNITUMJJW-NRKLIOEPSA-N

物化性质

• 沸点：
  527.2±50.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.56
• 重原子数：
  29.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  164.12
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-acetyl-1-O-(2-glyceryl)-α-D-mannopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以90%的产率得到1-O-(2-glyceryl)-α-D-mannopyranoside
  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：

  2,3,4,6-四-O-乙酰基-1-溴-Alpha-D-甘露糖 在 palladium on activated charcoal 氢气 、 碘 、 silver carbonate 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 120.0h， 生成 2,3,4,6-tetra-O-acetyl-1-O-(2-glyceryl)-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of Glycosyl Glycerols and Related Glycolipids

  摘要：

  Several isomeric glycosyl glycerols were synthesized. Acetylated allyl glycosides of D-glucose and D-galactose were transformed into 1-O-(glycopyranosyl)-rac-glycerols in a three step procedure via the corresponding 2,3-epoxypropyl glycosides and the peracetylated glycosyl glycerols. Tetra-O-benzyl-D-glucose was glycosylated with 1,3-di-O-benzylglycerol to give the alpha-anomer preferentially. The 2-O-(tetra-O-acetyl-beta-glycopyranosyl)-sn-glycerols and 2-O-(beta-glycopyranosyl)-sn-glycerols of D-glucose, D-galactose and N-acetyl-D-glucosamine and the corresponding alpha-derivatives of D-mannose were synthesized by selective glycosylation methods from 1,3-di-O-benzylglycerol and 1,3-O-benzylideneglycerol, respectively, and activated sugar compounds followed by hydrogenolysis. After long chain acylation and selective deacetylation the 1,3-di-O-acyl-2-O-(beta-glycopyranosyl)-sn-glycerols of D-glucose, D-galactose and N-acetyl-D-glucosamine and the corresponding a-derivative of D-mannose were synthesized.

  DOI：

  10.1080/07328309808007465