1,3-di-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2-deoxy-2-amino-glycerol | 809270-17-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1,3-di-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2-deoxy-2-amino-glycerol
• 英文别名: 2-amino-1,3-di-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)propane
• CAS: 809270-17-5
• 化学式: C₃₁H₄₅NO₂₀
• 分子量: 751.693
• InChiKey: MJYOFYYMHKXWDE-GNZBLXBPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.49
• 重原子数：
  52.0
• 可旋转键数：
  16.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  273.34
• 氢给体数：
  1.0
• 氢受体数：
  21.0

反应信息

• 作为反应物：
  描述：

  1,3-di-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2-deoxy-2-amino-glycerol 在 吡啶 、 甲醇 、 sodium methylate 作用下， 以 二氯甲烷 为溶剂， 生成 N-(palmitoyl)-1,3-di-O-(β-D-glucopyranosyl)-2-deoxy-2-amino-glycerol
  参考文献：
  名称：

  Synthesis and mesogenic properties of a Y-shaped glyco-glycero-lipid

  摘要：

  We synthesised a new glycoglycerolipid [1,3-di-O-(beta-D-glucopyranosyl)-2-deoxy-2-amino-N-palmitoyl-sn-glycerol] with a Y-shaped structure bearing two sugar head groups and only one fatty acid chain. Instead of an ester linkage between the glycerol and the fatty acid an amido function was introduced. The mesogenic properties were investigated using polarising microscopy and are discussed with respect to similar compounds. The lyotropism, was measured using the contact preparation method and small-angle neutron-scattering. (C) 2004 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2004.03.011
• 作为产物：
  描述：

  β-D-葡萄糖五乙酸酯 在 palladium on activated charcoal 、 三氟化硼乙醚 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、400.01 kPa 条件下， 反应 30.0h， 生成 1,3-di-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2-deoxy-2-amino-glycerol
  参考文献：
  名称：

  Synthesis of a series of multivalent homo-, and heteroglycosides and their anti-adhesion activities

  摘要：

  Adhesion of leukocytes to endothelium plays an important role in inflammatory diseases. We previously found that the tetravalent lactoside Gu-4 was able to inhibit leukocyte-endothelial cell adhesion significantly and that CD11b was the target of Gu-4 on the surface of leukocytes. In this report, we aimed to explore the relationship between structural characteristics of glycoclusters and anti-adhesion activity. Using selective glycosylation method and convergent strategy, we synthesized a new series of homoglycoclusters and heteroglycoclusters with diverse structures. And the bioactivities of these compounds were assessed by a static state cell-based adhesion assay. We found that when the linked saccharide fragments are the same, the anti-adhesion activities of compounds with flexible linkers were stronger than those with rigid scaffold such as the benzene ring, and the best flexible linker in the tested compounds was L-glutamic acid. When L-glutamic acid was employed as the linker, glycoclusters with four valences, but not other valences, exhibited the most significant anti-adhesion activity; however, no significant differences in anti-adhesion activity were found among the tetravalentglycosides that were made by linking glucose (32), mannose (TMa-4), cellobiose (34), or lactose (Gu-4). Thus, we conclude that a flexible linker with proper length, such as that of L-glutamic acid, and the linking of four saccharide fragments might be the preferable structural characteristics for the glycocluster compounds with potent anti-adhesion activity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.06.011

文献信息

• Synthesis of a series of new glycoclusters and the evaluation of their anti-adhesion activities
  作者：Xiaorong Zhang、Aqin Liu、Zhihui Zhao、Zhongjun Li、Qing Li

  DOI：10.1016/j.carres.2017.08.013

  日期：2017.10

  cellose and lactose residues showed good anti-adhesion activity of leukocytes to endothelial cells and exerted anti-inflammatory effects. Based on these results and combination principles of drugs, a series of new glycoclusters modifying with potentially anti-oxidant activity pharmacophores have been synthesized, and their anti-adhesion activities were assessed by static state cell-based adhesion assay

  根据我们的早期研究，一些具有葡萄糖，甘露糖，纤维素和乳糖残基的糖团显示出良好的白细胞对内皮细胞的抗粘附活性，并发挥了抗炎作用。基于这些结果和药物的组合原理，已合成了一系列用潜在的抗氧化活性药效团修饰的新糖簇，并通过基于静态细胞的粘附测定法评估了它们的抗粘附活性。结果表明，某些修饰的糖簇显示出比其先导化合物更好的活性。