1-(α-D-mannopyranosyl)propane | 141042-23-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(α-D-mannopyranosyl)propane
• 英文别名: (2R,3S,4R,5S,6R)-2-(hydroxymethyl)-6-propyloxane-3,4,5-triol
• CAS: 141042-23-1
• 化学式: C₉H₁₈O₅
• 分子量: 206.239
• InChiKey: PNQDGCOQVLHKHH-JGKVKWKGSA-N

物化性质

• 沸点：
  383.1±42.0 °C(Predicted)
• 密度：
  1.280±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  90.2
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)propene 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以93%的产率得到1-(α-D-mannopyranosyl)propane
  参考文献：
  名称：

  C-glycosyl compounds bind to receptors on the surface of Escherichia coli and can target proteins to the organism

  摘要：

  A series of C-mannopyranosyl derivatives have been synthesized and their inhibitory activity towards the receptor-mediated adhesion of E. coli to yeast cells has been tested. Total inhibition of yeast-cell agglutination by C-glycosyl derivatives 4 and 9 is achieved at a concentration approximately one order of magnitude lower than that of methyl alpha-D-mannopyranoside, indicating that the binding affinity to the receptor is related to the hydrophobicity of the carbon-linked side chain. A biotin-linked C-glycosyl derivative of mannose (compound 9) has been synthesized and used to target avidin and streptavidin to the bacterial cell surface. Of the C-glycosyl derivatives tested in our study, the conjugate of compound 9 with avidin had the highest avidity for the bacterial receptors, inhibiting agglutination at a concentration three orders of magnitude lower than methyl alpha-D-mannopyranoside. The use of such bifunctional compounds as the mannose-biotin conjugate 9 is a general strategy to target molecules to pathogenic organisms via their cell-surface carbohydrate receptors and to change the antigenicity of the bacterial cell surface.

  DOI：

  10.1016/0008-6215(92)80021-r

文献信息

• Sites for Dynamic Protein-Carbohydrate Interactions of O- and C-Linked Mannosides on the E. coli FimH Adhesin
  作者：Mohamed Touaibia、Eva-Maria Krammer、Tze Shiao、Nao Yamakawa、Qingan Wang、Anja Glinschert、Alex Papadopoulos、Leila Mousavifar、Emmanuel Maes、Stefan Oscarson、Gerard Vergoten、Marc Lensink、René Roy、Julie Bouckaert

  DOI：10.3390/molecules22071101

  日期：——

  amide, or sulfonamide were investigated to fit a hydrophobic substituent with up to two aryl groups within the tyrosine gate emerging from the mannose-binding pocket of FimH. The results were summarized into a set of structure-activity relationships to be used in FimH-targeted inhibitor design: alkene linkers gave an improved affinity and inhibitory potential, because of their relative flexibility combined

  大肠杆菌1型纤维粘附素FimH的拮抗剂被公认为是针对急性和复发性细菌感染的抗生素疗法和预防剂的诱人替代品。在这项研究中，研究了与烷基，烯烃，炔烃，硫代烷基，酰胺或磺酰胺O-或C-连接的α-d-甘露糖吡喃糖苷，以使疏水取代基在甘露糖-酪氨酸的酪氨酸门内具有最多两个芳基。 FimH的装订袋。结果总结为一组结构-活性关系，可用于以FimH为靶标的抑制剂设计：烯烃连接基具有相对​​的柔韧性以及与位于中间的异亮氨酸52的良好相互作用，从而提高了亲和力和抑制潜力酪氨酸门。特别令人感兴趣的是C联甘露糖苷，与邻取代联苯连接的烯烃，其亲和力类似于其O-甘露糖苷类似物，但优于其对位取代类似物。其高分辨率NMR溶液结构与FimH粘附素的对接表明，其最终的，邻位的苯环能够与异亮氨酸13相互作用，该异亮氨酸位于钳环中，并在施加于细菌的剪切力作用下发生构象变化。分子动力学模拟证实，C-甘露糖苷构象子的亚群能够在Fim