phenyl 3,4,5-tri-O-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-1-thio-β-D-galactopyranoside | 847359-70-0

• 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: phenyl 3,4,5-tri-O-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-1-thio-β-D-galactopyranoside
• 英文别名: phenyl 3,4,6-tri-O-acetyl-2-O-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-1-thio-β-D-galactopyranoside
• CAS: 847359-70-0
• 化学式: C₃₀H₃₈O₁₅S
• 分子量: 670.689
• InChiKey: HDUZADDAHUSRNE-SLVBLLCYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.86
• 重原子数：
  46.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  185.49
• 氢给体数：
  0.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  phenyl 3,4,5-tri-O-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-1-thio-β-D-galactopyranoside 在 N-碘代丁二酰亚胺 、 4 A molecular sieve 、 silver trifluoromethanesulfonate 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 14.0h， 生成 (2S,3S,4R,5S,6S)-2-{(2R,3R,4S,5R,6R)-2-[2-(2-Amino-ethoxy)-ethoxy]-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yloxy}-6-methyl-tetrahydro-pyran-3,4,5-triol
  参考文献：
  名称：

  A Role for Fucose α(1−2) Galactose Carbohydrates in Neuronal Growth

  摘要：

  We report a fucose alpha(1-2) galactose-mediated pathway for the modulation of neuronal growth and morphology. Our studies provide strong evidence for the presence of Fucalpha(1-2)Gal glycoproteins and lectin receptors in hippocampal neurons. Additionally, we show that manipulation of Fucalpha(1-2)Gal-associated proteins using small-molecule and lectin probes induces dramatic changes in neuronal morphology. These findings may provide a novel pathway to stimulate neuronal growth and regeneration.

  DOI：

  10.1021/ja044631v
• 作为产物：
  描述：

  3,4-di-O-acetyl-1,6-anhydro-2-O-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-β-D-galactopyranose 在 吡啶 、 zinc(II) iodide 作用下， 以 二氯甲烷 为溶剂， 反应 21.33h， 生成 phenyl 3,4,5-tri-O-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  A Role for Fucose α(1−2) Galactose Carbohydrates in Neuronal Growth

  摘要：

  We report a fucose alpha(1-2) galactose-mediated pathway for the modulation of neuronal growth and morphology. Our studies provide strong evidence for the presence of Fucalpha(1-2)Gal glycoproteins and lectin receptors in hippocampal neurons. Additionally, we show that manipulation of Fucalpha(1-2)Gal-associated proteins using small-molecule and lectin probes induces dramatic changes in neuronal morphology. These findings may provide a novel pathway to stimulate neuronal growth and regeneration.

  DOI：

  10.1021/ja044631v

文献信息

• Carbohydrate modifiers of neuronal growth
  申请人：Kalovidouris Stacey

  公开号：US20060177413A1

  公开（公告）日：2006-08-10

  Fucose galactose carbohydrates have been shown to induce neuronal outgrowth. The invention includes methods of inducing neuronal outgrowth using carbohydrates, assemblies, and polymers bearing fucose-galactose moieties, as well as associated proteins. Cell growth can be stimulated in cells in culture or in cells within an animal or patient. Growth stimulation has application to understanding and treatment of neurodegenerative diseases including, for example, Parkinson's disease, Alzheimer's disease and multiple sclerosis and conditions such as stroke, brain injury and spinal cord injury. Such compounds, polymers, and assemblies also can be used to increase neural stem or progenitor cells in culture or in an animal, and to enervate engineered tissue.

  富糖半乳糖碳水化合物已被证明能诱导神经突出生长。该发明涉及利用富糖半乳糖基团、相关蛋白质的碳水化合物、组装体和聚合物诱导神经突出生长的方法。细胞生长可以在培养细胞中或动物或患者体内的细胞中被刺激。生长刺激对于理解和治疗神经退行性疾病具有应用，例如帕金森病、阿尔茨海默病、多发性硬化症以及中风、脑损伤和脊髓损伤等疾病。这些化合物、聚合物和组装体还可以用于增加培养细胞或动物中的神经干细胞或祖细胞，并使工程组织恢复活力。